Stereoselective Synthesis of (E)- and (Z)-Fluoroalkenylboronates Using 2-Fluoroalkylideneiodonium Ylides Generated from (2-Fluoro-1-alkenyl)iodonium Salts

 

Tong Guan, Masanori Yoshida, and Shoji Hara*
Graduate School of Engineering, Hokkaido UniVersity, Sapporo 060-8628, Japan
shara@eng.hokudai.ac.jp
ReceiVed August 15, 2007

 

Introduction
Transition metal-catalyzed cross-coupling reactions of alkenylmetals with aryl or alkenyl halides have been successfully used for the stereoselective synthesis of alkenes with various functional groups.1 Although (fluoroalkenyl)metals, such as (1-fluoroalkenyl)metals,2 (1,2-difluoroalkenyl)metals,3 and (2,2-difluoroalkenyl)metals,4 have been used as versatile building blocks for fluoroalkene synthesis by cross-coupling reactions,5 (2-fluoroalkenyl)metals have not been used for the crosscoupling reactions. Recently, we reported the stereoselective synthesis of (E)- and (Z)-(2-fluoroalkenyl)iodonium salts (1)6
and their use for the synthesis of various fluoroalkenes by crosscoupling reactions.7 Quite recently, we succeeded in generation of 2-fluoroalkylideneiodonium ylides from 1 and their use for the stereoselective synthesis of (E)- and (Z)-dialkyl(2-fluoro-alkenyl)boranes (2a) by the reaction with trialkylboranes (Scheme 1).8 Though R-hydrogen of alkenyliodonium salts is known to be acidic and is readily abstracted by base, the generated iodonium ylide is unstable and decomposes to a carbene species quickly.9 By treatment of 1 with LDA in the presence of trialkylborane, the generated iodonium ylide made a borate complex with trialkylborane before decomposition to the carbene. Migration of an alkyl group from the boron to R-carbon with inversion of sp2 carbon took place as in the reaction of R-haloalkenylborates to give 2a stereoselectively.10

However, the resulting dialkyl(2-fluoroalkenyl)borane 2a is not stable enough to isolate by column chromatography, and we converted it to 2-fluoroalkene, 1-iodo-2-fluoroalkene, and R-fluoroketone without isolation.8 (2-Fluoroalkenyl)boronate (2b) is more stable than 2a and suitable for isolation. In particular, a pinacol ester is highly stable and can be purified by silica gel column chromatography.11 Therefore, we examined the reaction of the iodonium ylide with various alkylboronate derivatives for the preparation of 2b (Scheme 1).

 

Results and Discussion
Synthesis of (Fluoroalkenyl)boronates. We applied hexylboronate derivatives of various alcohols and phenols to the reaction with the iodonium ylide generated from the (Z)-2-fluorododecen-1-yliodonium salt (1a),7 and the yield was obtained after converting the product 2b to 8-fluorooctadecan-7-one (3) by oxidation (Table 1). The boronate derivatives of aliphatic alcohols are less reactive than that of phenols, and 3 was obtained only in poor yield (<10%) (entries 1, 2, 4, and5). On the other hand, B-hexylcatecholborane and hexyldiphenoxyborane gave 3 in 57% and 70% yields, respectively (entries
3 and 6). The best result was obtained using di(p-fluorophenoxy)hexylborane, which gave 3 in 82% yield (entry 7).

 

Di(p-fluorophenoxy)(8-fluoro-7-octadecenyl)borane, prepared by the reaction of 1a with di(p-fluorophenoxy)hexylborane, is moisture sensitive, and its purification by silica gel column chromatography is difficult. Therefore, we converted it to the stable pinacolborane derivative by transesterification12 and (E)-2-(8-fluorooctadec-7-en-7-yl)-4,4,5,5-tetramethyl[1,3,2]-dioxaborolane (4a) was obtained in 72% yield after purification by column chromatography. The (Z)-isomer (4b) was also obtained in 50% yield from the (E)-2-fluorododecen-1-yliodonium salt (1b)6 in a similar manner. The yield of 4b was lower
than that of 4a because of the instability of 4b.8 The stereochemistry of 4a and 4b was determined by two methods: observation of NOE in their 1H NMR spectra and their conversion to (Z)- and (E)-trisubstituted fluoroalkenes (5a and 5b). In 1H NMR of (E)-isomer 4a, NOE interaction was observed between the protons attached to the allylic carbons.

 

On the other hand, the NOE interaction of the allylic protons was not observed in (Z)-isomer 4b (Scheme 2). By the Suzuki-Miyaura coupling reaction with iodobenzene, 4a and 4b were converted to (Z)- and (E)-7-phenyl-8-fluorooctadec-7-ene (5a) and (5b), respectively,1b and their spectra data were in good agreement with the previously reported data (Scheme 3).8 These results support the (E)- and (Z)-stereochemistry of 4a and 4b.

 

From various (fluoroalkenyl)iodonium salts (1a-f), corresponding (fluoroalkenyl)boronates (4a-h) were obtained stereoselectively (Table 2). (Fluoroalkenyl)iodonium salts with functional groups such as acetate (1c), benzyl ether (1d), ester (1e), and acetal (1f) can be prepared from corresponding alkynes,6 and the corresponding functionalized (fluoroalkenyl)-boronates (4c-f) can be prepared from them. Introduction of the functional groups into 4 using the functionalized alkylboronates is also possible. Using di(p-fluorophenoxy)(3-bromopropyl)borane, the (1-bromo-5-fluoropentadecan-4-en-4 yl)boronate (4h) was obtained. An alkenylboronate can be also used for the reaction: for example, from di(p-fluorophenoxy)hex-1-en-1-ylborane, (8-fluorooctadeca-5,7-dien-7-yl)boronate (4g) was
obtained stereoselectively.

 

 

Application of (Fluoroalkenyl)boronates in the SuzukiMiyaura Coupling Reaction. The resulting (fluoroalkenyl)-boronates were used in the Suzuki-Miyaura coupling reaction for the synthesis of polyfunctionalized trisubstituted fluoroalkenes (Table 3).1b The cross-coupling reactions with aryl halides or alkenyl halides proceeded stereospecifically, and from (E)-(fluoroalkenyl)boronates (4a,e-g), arylated (Z)-fluoroalkenes (5a, 6, 8) or fluoroalkadienes (7, 9, 10) were obtained. On the other hand, from (Z)-isomer (4b), (E)-fluoroalkene (5b) was selectively formed. The functional groups such as ester, acetal can tolerate the reaction conditions, and corresponding polyfunctionalized arylated fluoroalkene (8) or fluoroalkadiene (9) was obtained stereoselectively. Though we did not optimized the conditions of the cross-coupling well, lower reaction temperature (80-85 °C) is preferable for the functionalized fluoroalkene synthesis.

Summary
We succeeded in the stereoselective synthesis of (fluoroalkenyl)boronates by the reaction of alkylideneiodonium ylide generated from (fluoroalkenyl)iodonium salts with di(p-fluorophenoxy)alkylborane. The (fluoroalkenyl)boronates were isolated as stable pinacol esters. Starting from (E)- or (Z)-fluoroalkenyliodonium salts, (E)- or (Z)-(fluoroalkenyl)boronates can be prepared stereoselectively. Various functional groups can be introduced into the (fluoroalkenyl)boronates using functionalized (fluoroalkenyl)iodonium salts or functionalized alkylboronates. The resulting (E)- and (Z)-(fluoroalkenyl)boronates can be used in a cross-coupling reaction with aryl or alkenyl halides for the synthesis of trisubstituted fluoroalkenes.
 

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CAS No. 1015-97-0 1H-Benz[f]indazole-4,9-dione Catalog No.:AG0004MQ MDL No.: MF:C11H6N2O2 MW:198.1775	CAS No. 10150-19-3 Urea, N-(9,10-dihydro-4-hydroxy-9,10-dioxo-1-anthracenyl)-N'-phenyl- Catalog No.:AG0004NY MDL No.: MF:C21H14N2O4 MW:358.3469	CAS No. 10150-27-3 Pyridine, 2-[2-(diphenylphosphino)ethyl]- Catalog No.:AG0004NX MDL No.: MF:C19H18NP MW:291.3267
CAS No. 10150-40-0 1,2-Ethanediamine, N1,N2-dicyclopentyl-, hydrochloride (1:2) Catalog No.:AG0004NW MDL No.: MF:C12H26Cl2N2 MW:269.2542	CAS No. 10150-87-5 2-Butanone, 4-(acetyloxy)- Catalog No.:AG0004NV MDL No.:MFCD00010230 MF:C6H10O3 MW:130.1418	CAS No. 10150-92-2 2-Pentenoic acid, 4-hydroxy-, ethyl ester, (2E)- Catalog No.:AG0004NU MDL No.: MF:C7H12O3 MW:144.1684
CAS No. 10150-93-3 2-Pentenoic acid, 4-oxo-, ethyl ester, (2E)- Catalog No.:AG0004NT MDL No.:MFCD00100521 MF:C7H10O3 MW:142.1525	CAS No. 101500-22-5 Benzaldehyde, 3-bromo-4-(octyloxy)- Catalog No.:AG0004NS MDL No.:MFCD18586003 MF:C15H21BrO2 MW:313.2300	CAS No. 101500-64-5 Furo[3'',4'':3',4']cyclobuta[1',2':3,4]cyclobut[1,2-d]isoxazole (9CI) Catalog No.:AG0004NR MDL No.: MF:C9H3NO2 MW:157.1256
CAS No. 101502-01-6 Ethanedioic acid, 1,2-bis[2-[3-oxo-3-[(phenylmethyl)amino]propyl]hydrazide] Catalog No.:AG0004NQ MDL No.: MF:C22H28N6O4 MW:440.4955	CAS No. 101504-83-0 2-Propenoic acid, 2-methyl-, 2,3-dihydroxybutyl ester Catalog No.:AG0004NP MDL No.: MF:C8H14O4 MW:174.1944	CAS No. 1015056-80-0 Pyridine, 4-ethyl-2,3,5-trimethyl-, 1-oxide Catalog No.:AG0004NK MDL No.:MFCD23135318 MF:C10H15NO MW:165.2322
CAS No. 1015056-89-9 2-Pyridinemethanol, 4-ethyl-3,5-dimethyl-, 2-acetate Catalog No.:AG0004NJ MDL No.: MF:C12H17NO2 MW:207.2689	CAS No. 1015056-94-6 Pyridine, 2-(chloromethyl)-4-ethyl-3,5-dimethyl-, hydrochloride (1:1) Catalog No.:AG0004NI MDL No.:MFCD18909274 MF:C10H15Cl2N MW:220.1388	CAS No. 101506-39-2 Carbamic acid, N-octyl-, 1,1-dimethylethyl ester Catalog No.:AG0004NO MDL No.: MF:C13H27NO2 MW:229.3590
CAS No. 101506-43-8 Carbonothioic acid, O-(1-chloroethyl) S-ethyl ester Catalog No.:AG0004NN MDL No.: MF:C5H9ClO2S MW:168.6418	CAS No. 101506-88-1 1H-Indol-3-ol, 1-[2-[[(4-methylphenyl)sulfonyl]amino]-1-oxopropyl]-, (S)- (9CI) Catalog No.:AG0004NM MDL No.: MF:C18H18N2O4S MW:358.4115	CAS No. 1015060-26-0 Pyridine, 3-bromo-2-(bromomethyl)-6-ethoxy-, hydrobromide (1:1) Catalog No.:AG0004NH MDL No.:MFCD14706826 MF:C8H10Br3NO MW:375.8831
CAS No. 1015060-31-7 Pyridine, 5-bromo-2-(chloromethyl)-3-methyl- Catalog No.:AG0004NG MDL No.:MFCD18254357 MF:C7H7BrClN MW:220.4942	CAS No. 1015068-44-6 6-Isoquinolinecarboxylic acid, hydrazide Catalog No.:AG0004NF MDL No.:MFCD22201122 MF:C10H9N3O MW:187.1980	CAS No. 1015068-75-3 1H-Indazole-1,5-dicarboxylic acid, 3-Methyl-, 1-(1,1-diMethylethyl) 5-Methyl ester Catalog No.:AG0004NE MDL No.:MFCD13182983 MF:C15H18N2O4 MW:290.3144
CAS No. 1015068-76-4 1H-Indazole-5-carboxylic acid, 3-methyl-, methyl ester Catalog No.:AG0004ND MDL No.:MFCD22628068 MF:C10H10N2O2 MW:190.1986	CAS No. 101507-15-7 1-Naphthalenecarboxamide, 1,4-dihydro-N-(2-methyl-1-phenylpropyl)- Catalog No.:AG0004NL MDL No.: MF:C21H23NO MW:305.4134	CAS No. 1015070-56-0 4-Isoquinolinol, 6-bromo- Catalog No.:AG0004NC MDL No.:MFCD18257891 MF:C9H6BrNO MW:224.0540
CAS No. 1015070-57-1 Isoquinoline, 6-ethynyl- Catalog No.:AG0004NB MDL No.:MFCD12406191 MF:C11H7N MW:153.1800	CAS No. 1015070-59-3 Benzenepropanoic acid, α-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]- Catalog No.:AG0004NA MDL No.: MF:C16H23NO4 MW:293.3581	CAS No. 1015070-97-9 1,2-Benzisothiazole-6-carboxylic acid Catalog No.:AG0004O5 MDL No.:MFCD19687659 MF:C8H5NO2S MW:179.1958
CAS No. 1015071-22-3 2,3-Thiophenedicarboxaldehyde, 5-fluoro- Catalog No.:AG0004O4 MDL No.:MFCD15143649 MF:C6H3FO2S MW:158.1502	CAS No. 1015078-03-1 5-Quinolinecarboxaldehyde, 3-methyl- Catalog No.:AG0004O3 MDL No.: MF:C11H9NO MW:171.1953	CAS No. 101508-72-9 Phosphonic acid, [(butylamino)-3-pyridinylmethyl]- (9CI) Catalog No.:AG0004OK MDL No.: MF:C10H17N2O3P MW:244.2273
CAS No. 1015082-71-9 Borate(1-), trifluoro(4-hydroxyphenyl)-, potassium (1:1), (T-4)- Catalog No.:AG0004O2 MDL No.:MFCD09992974 MF:C6H5BF3K2O MW:239.1061	CAS No. 1015082-77-5 Borate(1-), trifluoro[3-(hydroxymethyl)phenyl]-, potassium (1:1), (T-4)- Catalog No.:AG0004O1 MDL No.:MFCD09993091 MF:C7H7BF3KO MW:214.0344	CAS No. 1015082-78-6 Borate(1-), trifluoro[4-(hydroxymethyl)phenyl]-, potassium (1:1), (T-4)- Catalog No.:AG0004O0 MDL No.:MFCD08276800 MF:C7H7BF3KO MW:214.0344
CAS No. 1015082-80-0 Borate(1-), trifluoro[3-(2-hydroxyethyl)phenyl]-, potassium (1:1), (T-4)- Catalog No.:AG0004NZ MDL No.: MF: MW:	CAS No. 101509-27-7 Sulfuric acid, neodymium(3+) salt, hydrate (9CI) Catalog No.:AG0004OJ MDL No.:MFCD00149802 MF:H8Nd2O13S3 MW:600.7307	CAS No. 101509-46-0 Benzoic acid, 2-[[(5-carboxypentyl)amino]carbonyl]- Catalog No.:AG0004OI MDL No.: MF:C14H17NO5 MW:279.2885
CAS No. 10151-02-7 Formamide, N-(1,1,3,3-tetramethylbutyl)- Catalog No.:AG0004ON MDL No.:MFCD00039569 MF:C9H19NO MW:157.2533	CAS No. 10151-46-9 2-Naphthalenesulfonic acid, hydrazide Catalog No.:AG0004OM MDL No.:MFCD00596250 MF:C10H10N2O2S MW:222.2636	CAS No. 10151-95-8 Acetamide, 2-nitro-N-phenyl- Catalog No.:AG0004OL MDL No.: MF:C8H8N2O3 MW:180.1607
CAS No. 101510-87-6 L-Lysine, glycyl-L-leucyl-L-leucyl-L-α-aspartyl-L-leucyl- Catalog No.:AG0004OH MDL No.: MF:C30H55N7O9 MW:657.7992	CAS No. 101511-34-6 Benzoic acid, 4-hydroxy-3-(3-methyl-2-buten-1-yl)-, methyl ester Catalog No.:AG0004OG MDL No.: MF:C13H16O3 MW:220.2643	CAS No. 101511-71-1 Benzenamine, N-[3-(dimethoxymethylsilyl)propyl]- Catalog No.:AG0004OF MDL No.: MF:C12H21NO2Si MW:239.3861
CAS No. 101511-85-7 Cyclohexanone, 2-(2-methylpropylidene)-, oxime Catalog No.:AG0004OE MDL No.: MF:C10H17NO MW:167.2481	CAS No. 101512-07-6 9-Anthraceneacetic acid, ethyl ester Catalog No.:AG0004OD MDL No.: MF:C18H16O2 MW:264.3184	CAS No. 101512-21-4 3-Pyridinecarboxamide, 5-hydroxy- Catalog No.:AG0004OC MDL No.:MFCD01199201 MF:C6H6N2O2 MW:138.1240
CAS No. 101512-22-5 3-Pyridinecarboxylic acid, 5-(benzoylamino)-, ethyl ester Catalog No.:AG0004OB MDL No.: MF:C15H14N2O3 MW:270.2833	CAS No. 101512-30-5 Adenosine, 5'-S-[4-(aminooxy)butyl]-5'-thio- (9CI) Catalog No.:AG0004OA MDL No.: MF:C14H22N6O4S MW:370.4273	CAS No. 101512-39-4 Phenol, 2-[[[3-(dimethylamino)propyl]imino]methyl]- Catalog No.:AG0004O9 MDL No.: MF:C12H18N2O MW:206.2841
CAS No. 101512-65-6 Propanedinitrile, 2-[[4-[bis(2-methoxyethyl)amino]phenyl]methylene]- Catalog No.:AG0004O8 MDL No.: MF:C16H19N3O2 MW:285.3410	CAS No. 101513-13-7 2-Naphthalenecarboxylic acid, 6-(1-methylethyl)-, methyl ester Catalog No.:AG0004O7 MDL No.: MF:C15H16O2 MW:228.2863	CAS No. 101513-14-8 2-Butenal, 4,4-bis(acetyloxy)-2-methyl-, (Z)- (9CI) Catalog No.:AG0004O6 MDL No.: MF:C9H12O5 MW:200.1886
CAS No. 101513-20-6 Benzenamine, 4-[(4-aminophenyl)sulfonyl]-N,3-dimethyl- Catalog No.:AG0004PB MDL No.: MF:C14H16N2O2S MW:276.3540	CAS No. 101513-21-7 Benzenamine, 4-[(4-aminophenyl)sulfonyl]-3-methyl-N-propyl- Catalog No.:AG0004PA MDL No.: MF:C16H20N2O2S MW:304.4072	CAS No. 101513-22-8 Benzenamine, 4-[(4-aminophenyl)sulfonyl]-3-chloro-N-ethyl- Catalog No.:AG0004P9 MDL No.: MF:C14H15ClN2O2S MW:310.7991
CAS No. 101513-60-4 Benzenamine, 2-chloro-N-methyl-5-nitro- Catalog No.:AG0004P8 MDL No.: MF:C7H7ClN2O2 MW:186.5957	CAS No. 101513-69-3 Benzoyl fluoride, 5-chloro-2,3,4-trifluoro- Catalog No.:AG0004P7 MDL No.: MF:C7HClF4O MW:212.5289	CAS No. 101513-72-8 Benzoyl chloride, 3,5-dichloro-2,4-difluoro- Catalog No.:AG0004P6 MDL No.: MF:C7HCl3F2O MW:245.4380
CAS No. 101513-77-3 Benzoic acid, 3-chloro-2,4,5-trifluoro- Catalog No.:AG0004P5 MDL No.:MFCD00153101 MF:C7H2ClF3O2 MW:210.5378	CAS No. 101513-78-4 Benzoyl chloride, 3-chloro-2,4,5-trifluoro- Catalog No.:AG0004P4 MDL No.:MFCD04039245 MF:C7HCl2F3O MW:228.9834	CAS No. 101513-80-8 Benzaldehyde, 3-chloro-2,4,5-trifluoro- Catalog No.:AG0004P3 MDL No.:MFCD04972744 MF:C7H2ClF3O MW:194.5384
CAS No. 101513-85-3 Benzamide, 3-chloro-2,4,5-trifluoro- Catalog No.:AG0004P2 MDL No.: MF:C7H3ClF3NO MW:209.5530	CAS No. 101514-23-2 2-Cyclohexen-1-one, 6-hydroxy-3-methyl- Catalog No.:AG0004P1 MDL No.:MFCD24689479 MF:C7H10O2 MW:126.1531	CAS No. 101515-22-4 Benzenamine, N-[[4-(hexyloxy)phenyl]methylene]-4-pentyl-, [N(E)]- Catalog No.:AG0004P0 MDL No.: MF:C24H33NO MW:351.5249
CAS No. 101515-65-5 Oxaziridine, 2-chloro-3,3-bis(1,1-dimethylethyl)- Catalog No.:AG0004OZ MDL No.: MF:C9H18ClNO MW:191.6983	CAS No. 101515-66-6 Pentane, 3-chloro-2,2,4,4-tetramethyl-3-nitroso- Catalog No.:AG0004OY MDL No.: MF:C9H18ClNO MW:191.6983	CAS No. 101516-96-5 Carbamic acid, 1,3-benzodioxol-5-yl-, 2-(2-pyridinyl)ethyl ester (9CI) Catalog No.:AG0004OX MDL No.: MF:C15H14N2O4 MW:286.2827
CAS No. 101516-97-6 Glycine, N-[[(4-methoxy-1-naphthalenyl)amino]carbonyl]-, ethyl ester Catalog No.:AG0004OW MDL No.: MF:C16H18N2O4 MW:302.3251	CAS No. 101516-99-8 Glycine, N-[[[(4-hydroxy-3-methoxyphenyl)methyl]amino]thioxomethyl]-, butyl ester Catalog No.:AG0004OV MDL No.: MF:C15H22N2O4S MW:326.4112	CAS No. 101517-00-4 Hydrazinecarboximidamide, N-1-naphthalenyl-, hydriodide (1:1) Catalog No.:AG0004OU MDL No.: MF: MW:
CAS No. 101517-04-8 Guanidine, N-(1,1-dimethylethyl)-N'-2-thiazolyl-, (2Z)-2-butenedioate (1:1) Catalog No.:AG0004OT MDL No.: MF:C12H18N4O4S MW:314.3607	CAS No. 101517-06-0 Guanidine, N-dodecyl-N'-nitro- (9CI) Catalog No.:AG0004OS MDL No.: MF:C13H28N4O2 MW:272.3870	CAS No. 101517-07-1 Guanidine, N-[2-(3,4,5,6-tetrahydro-1-benzazocin-1(2H)-yl)ethyl]-, hydriodide (1:1) Catalog No.:AG0004OR MDL No.: MF:C19H16N2O5 MW:352.3407
CAS No. 101517-09-3 Guanidine, [(4-methoxy-1-naphthalenyl)methyl]-, sulfate (2:1) (9CI) Catalog No.:AG0004OQ MDL No.: MF:C13H17N3O5S MW:327.3562	CAS No. 101517-14-0 Heptanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-[(1-methylethyl)thio]- Catalog No.:AG0004OP MDL No.: MF:C18H29NO3S MW:339.4928	CAS No. 101517-71-9 2-Butenoic acid, 2-methyl-4-oxo-4-phenyl-, ethyl ester, (2E)- Catalog No.:AG0004OO MDL No.: MF:C13H14O3 MW:218.2485
CAS No. 101517-79-7 4H-1,3,5-Dithiazine, 4-butyldihydro-2,6-dimethyl- Catalog No.:AG0004PR MDL No.: MF:C9H19NS2 MW:205.3839	CAS No. 101517-87-7 4H-1,3,5-Dithiazine, dihydro-4,6-dimethyl-2-(2-methylpropyl)- Catalog No.:AG0004PQ MDL No.:MFCD10000649 MF:C9H19NS2 MW:205.3839	CAS No. 101517-94-6 1,2,3,5,6-Pentathiepane, 4,7-dimethyl- Catalog No.:AG0004PP MDL No.: MF:C4H8S5 MW:216.4313
CAS No. 1015170-66-7 2,3-Diazaspiro[4.4]non-2-ene Catalog No.:AG0004PL MDL No.: MF:C7H12N2 MW:124.1836	CAS No. 101518-61-0 Benzenepropanamide, α,α-dimethyl- Catalog No.:AG0004PO MDL No.: MF:C11H15NO MW:177.2429	CAS No. 101519-68-0 Antimony, compd. with palladium (3:5) Catalog No.:AG0004PN MDL No.: MF:Pd5Sb3 MW:897.3800
CAS No. 10152-41-7 1,2-Propanediol, 3-(octadecyloxy)-, diacetate, (2R)- (9CI) Catalog No.:AG0004Q0 MDL No.: MF:C25H48O5 MW:428.6456	CAS No. 10152-42-8 1,2-Propanediol, 3-(hexadecyloxy)-, diacetate, (2R)- (9CI) Catalog No.:AG0004PZ MDL No.: MF:C23H44O5 MW:400.5925	CAS No. 10152-58-6 Oxirane, 2,2-dimethyl-3-phenyl- Catalog No.:AG0004PY MDL No.:MFCD21339443 MF:C10H12O MW:148.2017
CAS No. 10152-61-1 Cyclopropaneoctanoic acid, 2-hexyl-, methyl ester Catalog No.:AG0004PX MDL No.: MF:C18H34O2 MW:282.4614	CAS No. 10152-62-2 Cyclopropaneoctanoic acid, 2-octyl-, methyl ester Catalog No.:AG0004PW MDL No.: MF:C20H38O2 MW:310.5145	CAS No. 10152-65-5 Cyclopropanedodecanoic acid, 2-octyl-, methyl ester Catalog No.:AG0004PV MDL No.: MF:C24H46O2 MW:366.6208
CAS No. 10152-75-7 Ethyne, (methylthio)- (9CI) Catalog No.:AG0004PU MDL No.:MFCD17013351 MF:C3H4S MW:72.1289	CAS No. 10152-76-8 1-Propene, 3-(methylthio)- Catalog No.:AG0004PT MDL No.:MFCD00008657 MF:C4H8S MW:88.1713	CAS No. 10152-77-9 1-Propene,1-(methylthio)- Catalog No.:AG0004PS MDL No.:MFCD27996257 MF:C4H8S MW:88.1713
CAS No. 1015223-89-8 Propanal, 3-[[7-(benzoyloxy)thieno[3,2-b]pyridin-5-yl]amino]-, hydrochloride (1:1) Catalog No.:AG0004PK MDL No.: MF:C17H15ClN2O3S MW:362.8306	CAS No. 1015229-31-8 Boronic acid, B-[5-(2-methoxyethoxy)-3-pyridinyl]- Catalog No.:AG0004PJ MDL No.:MFCD13183780 MF:C8H12BNO4 MW:196.9962	CAS No. 1015236-21-1 Pteridine, 4-chloro-2-(5-chloro-2-fluorophenyl)- Catalog No.:AG0004PI MDL No.: MF:C12H5Cl2FN4 MW:295.0993
CAS No. 101524-04-3 4-Pyridinecarboxylic acid, 2-(1-oxohexadecyl)hydrazide Catalog No.:AG0004PM MDL No.: MF:C22H37N3O2 MW:375.5481	CAS No. 1015241-96-9 1H-Azepine, 1-(5-bromo-2-pyrimidinyl)hexahydro- Catalog No.:AG0004PH MDL No.:MFCD18903003 MF:C10H14BrN3 MW:256.1423	CAS No. 1015242-03-1 Piperazine, 1-(phenylmethyl)-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]- Catalog No.:AG0004PG MDL No.:MFCD06798275 MF:C22H30BN3O2 MW:379.3035
CAS No. 1015242-06-4 2-Pyrimidinamine, N-methyl-N-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG0004PF MDL No.:MFCD18734714 MF:C15H26BN3O2 MW:291.1968	CAS No. 1015242-07-5 Pyrimidine, 2-(1-pyrrolidinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG0004PE MDL No.:MFCD07781249 MF:C14H22BN3O2 MW:275.1544	CAS No. 1015242-08-6 Pyrimidine, 2-(1-piperidinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG0004PD MDL No.:MFCD07368250 MF:C15H24BN3O2 MW:289.1810
CAS No. 1015242-58-6 Boronic acid, B-(3,4-dihydro-4-methyl-2H-1,4-benzoxazin-6-yl)- Catalog No.:AG0004PC MDL No.:MFCD20441848 MF:C9H12BNO3 MW:193.0075	CAS No. 101526-61-8 1,2-Ethanediamine, N1-ethyl-N1-heptyl- Catalog No.:AG0004QL MDL No.: MF:C11H26N2 MW:186.3375	CAS No. 101527-45-1 Thymidine, α-fluoro- (9CI) Catalog No.:AG0004QK MDL No.: MF:C10H13FN2O5 MW:260.2190
CAS No. 101527-46-2 Thymidine, α,α-difluoro- (9CI) Catalog No.:AG0004QJ MDL No.: MF:C10H12F2N2O5 MW:278.2095	CAS No. 101527-68-8 2,4(1H,3H)-Pyrimidinedione, 1-[6-(hydroxymethyl)-1,4-dioxan-2-yl]-, (2R-cis)- (9CI) Catalog No.:AG0004QI MDL No.: MF:C9H12N2O5 MW:228.2020	CAS No. 101529-24-2 2H-1-Benzopyran-2-ethanol, 6-chloro-3,4-dihydro-2-methyl- Catalog No.:AG0004QH MDL No.: MF:C12H15ClO2 MW:226.6993
CAS No. 10153-22-7 1-Triazene, 3-(4-methoxyphenyl)-1-(4-methylphenyl)- Catalog No.:AG0004QP MDL No.: MF:C14H15N3O MW:241.2884	CAS No. 10153-31-8 2,4-Benzodithiepin, 1,5-dihydro-3,7,8-trimethyl- Catalog No.:AG0004QO MDL No.: MF:C12H16S2 MW:224.3854	CAS No. 10153-83-0 Pentanoic acid, 2,4-dioxo-, butyl ester Catalog No.:AG0004QN MDL No.: MF:C9H14O4 MW:186.2051
CAS No. 101530-10-3 1H-Imidazole-1-acetonitrile, α-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-, (αE)- Catalog No.:AG0004QG MDL No.:MFCD00865590 MF:C14H10ClN3S2 MW:319.8323	CAS No. 1015308-63-0 Propanal, 3-[[7-(benzoyloxy)thieno[3,2-b]pyridin-5-yl]amino]- Catalog No.:AG0004Q1 MDL No.: MF:C17H14N2O3S MW:326.3697	CAS No. 101531-22-0 Ethanone, 1-[2-(2-bromoethyl)phenyl]- Catalog No.:AG0004QF MDL No.: MF:C10H11BrO MW:227.0977
CAS No. 101532-23-4 Benzoic acid, 4-methoxy-, 2-propyn-1-yl ester Catalog No.:AG0004QE MDL No.: MF:C11H10O3 MW:190.1953	CAS No. 101532-38-1 Benzene, 1-bromo-4-(trans-4-heptylcyclohexyl)- Catalog No.:AG0004QD MDL No.: MF:C19H29Br MW:337.3376	CAS No. 101533-37-3 Benzothiazolium, 2-(dimethylamino)-3-methyl-, iodide (1:1) Catalog No.:AG0004QC MDL No.: MF:C10H13IN2S MW:320.1931
CAS No. 101533-70-4 Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-1-naphthalenyl ester Catalog No.:AG0004QB MDL No.: MF:C11H11F3O3S MW:280.2634	CAS No. 101533-94-2 2-Pentyne, 5-(methoxymethoxy)- Catalog No.:AG0004QA MDL No.: MF:C7H12O2 MW:128.1690	CAS No. 101536-75-8 6-Heptene-2,4-diol, 4-(2-propen-1-yl)- Catalog No.:AG0004Q9 MDL No.: MF:C10H18O2 MW:170.2487
CAS No. 101536-78-1 Benzoic acid, 3-chloro-5-ethyl-6-hydroxy-2-methoxy- Catalog No.:AG0004Q8 MDL No.: MF:C10H11ClO4 MW:230.6449	CAS No. 101537-09-1 2,5,8,11,14-Pentaoxapentadecane, 1,15-bis(2,5-dimethoxyphenyl)- Catalog No.:AG0004Q7 MDL No.: MF:C26H38O9 MW:494.5745	CAS No. 101537-17-1 1-Heptanaminium, N,N,N-triheptyl-, sulfate (1:1) Catalog No.:AG0004Q6 MDL No.: MF:C28H61NO4S MW:507.8532
CAS No. 101537-21-7 Ethene, 1,1-dibromo-2-chloro-2-methoxy- Catalog No.:AG0004Q5 MDL No.: MF:C3H3Br2ClO MW:250.3163	CAS No. 101537-26-2 Octane, 1-(ethynyloxy)- Catalog No.:AG0004Q4 MDL No.: MF:C10H18O MW:154.2493	CAS No. 101537-64-8 2-Thiophenecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]- Catalog No.:AG0004Q3 MDL No.:MFCD02682396 MF:C10H13NO4S MW:243.2795
CAS No. 101538-89-0 Benzamide, N-[cyano[(3-iodo-2-propyn-1-yl)oxy]methyl]- Catalog No.:AG0004Q2 MDL No.: MF:C12H9IN2O2 MW:340.1165	CAS No. 10154-04-8 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, butyl ester, (E,E)- (8CI,9CI) Catalog No.:AG0004QM MDL No.: MF:C21H36O2 MW:320.5093	CAS No. 10154-08-2 1H-Purine-8-propanoic acid, α-amino-2,3,6,7-tetrahydro-3,7-dimethyl-2,6-dioxo- Catalog No.:AG0004RE MDL No.: MF:C10H13N5O4 MW:267.2413
CAS No. 10154-10-6 9H-Purine-6-methanamine, 2-chloro-N,N-bis(2-chloroethyl)-9-methyl-, hydrochloride (1:1) Catalog No.:AG0004RD MDL No.: MF:C11H15Cl4N5 MW:359.0823	CAS No. 10154-54-8 1,3,2-Benzodioxaphosphol-2-amine, N-phenyl- Catalog No.:AG0004RC MDL No.: MF:C12H10NO2P MW:231.1871	CAS No. 10154-60-6 Benzenecarbothioic acid, S-2-naphthalenyl ester Catalog No.:AG0004RB MDL No.: MF:C17H12OS MW:264.3416
CAS No. 10154-63-9 Benzenesulfonic acid, 2,5-dichloro-, tetramethylene ester (7CI,8CI) Catalog No.:AG0004RA MDL No.: MF:C16H14Cl4O6S2 MW:508.2208	CAS No. 10154-71-9 Propanoic acid, 3-(phenylsulfonyl)- Catalog No.:AG0004R9 MDL No.:MFCD00010141 MF:C9H10O4S MW:214.2383	CAS No. 10154-72-0 Propanoic acid, 3-(phenylsulfonyl)-, methyl ester Catalog No.:AG0004R8 MDL No.: MF:C10H12O4S MW:228.2649
CAS No. 10154-75-3 Propanenitrile, 3-(phenylsulfonyl)- Catalog No.:AG0004R7 MDL No.:MFCD00047798 MF:C9H9NO2S MW:195.2383	CAS No. 10154-76-4 Propanoic acid, 3-[(4-methylphenyl)sulfonyl]- Catalog No.:AG0004R6 MDL No.:MFCD00222077 MF:C10H12O4S MW:228.2649	CAS No. 10154-77-5 Propanoic acid, 3-[(4-methylphenyl)sulfonyl]-, methyl ester Catalog No.:AG0004R5 MDL No.: MF:C11H14O4S MW:242.2915
CAS No. 10154-82-2 Benzenesulfonic acid, 2,5-dibromo-, 2-butynylene ester (7CI,8CI) Catalog No.:AG0004R4 MDL No.: MF:C16H10Br4O6S2 MW:681.9930	CAS No. 10154-84-4 Benzenesulfonic acid, m-nitro-, 2-butynylene ester (7CI,8CI) Catalog No.:AG0004R3 MDL No.: MF: MW:	CAS No. 10154-97-9 Propanoic acid, 2-[(4-hydroxy-1-naphthalenyl)oxy]- Catalog No.:AG0004R2 MDL No.: MF:C13H12O4 MW:232.2320
CAS No. 101540-56-1 Octadecadienoic acid, methyl ester, (Z,Z)- Catalog No.:AG0004R1 MDL No.: MF:C19H34O2 MW:294.4721	CAS No. 101540-79-8 Pyridine, 2-methyl-5-(1-methyl-2-pyrrolidinyl)- Catalog No.:AG0004R0 MDL No.: MF:C11H16N2 MW:176.2581	CAS No. 101541-79-1 Phenol, 2-[(triethylsilyl)oxy]- Catalog No.:AG0004QZ MDL No.: MF:C12H20O2Si MW:224.3715
CAS No. 101541-83-7 Phenol, 2-[(tributylsilyl)oxy]- Catalog No.:AG0004QY MDL No.: MF:C18H32O2Si MW:308.5310	CAS No. 1015423-45-6 1H,3H-Thieno[3,4-c]furan-1,3-dione, 4,6-dibromo- Catalog No.:AG0004QU MDL No.: MF:C6Br2O3S MW:311.9354	CAS No. 101543-67-3 Tricyclo[3.3.2.02,8]deca-3,6,9-triene,4-fluoro- (9CI) Catalog No.:AG0004QX MDL No.: MF:C10H9F MW:148.1769
CAS No. 1015433-96-1 Benzoic acid, 4,5-difluoro-2-nitro-, methyl ester Catalog No.:AG0004QT MDL No.:MFCD11042825 MF:C8H5F2NO4 MW:217.1264	CAS No. 101544-38-1 Ethanone, 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-[bis(phenylmethyl)amino]- Catalog No.:AG0004QW MDL No.: MF:C26H26N2O2 MW:398.4968	CAS No. 101544-49-4 1H-Indole-7-carboxamide, 5-(2-amino-1-hydroxyethyl)- Catalog No.:AG0004QV MDL No.: MF:C11H13N3O2 MW:219.2398
CAS No. 1015447-26-3 β-D-Ribofuranose, 4-thio-, 1-acetate 2,3,5-tribenzoate Catalog No.:AG0004QS MDL No.: MF: MW:	CAS No. 1015460-59-9 5H-Pyrido[4,3-b]indole, 7-bromo- Catalog No.:AG0004QR MDL No.:MFCD18803689 MF:C11H7BrN2 MW:247.0907	CAS No. 1015479-08-9 4(3H)-Quinazolinone, 6-methyl-2-(propylamino)- Catalog No.:AG0004QQ MDL No.:MFCD11053701 MF:C12H15N3O MW:217.2670
CAS No. 1015480-87-1 (3,6-Dimethoxypyridazin-4-yl)boronic acid Catalog No.:AG0004RH MDL No.:MFCD10700157 MF:C6H9BN2O4 MW:183.9577	CAS No. 1015481-14-7 Pyridazine, 3-methoxy-6-(6-methoxy-3-pyridinyl)- Catalog No.:AG0004RG MDL No.: MF:C11H11N3O2 MW:217.2239	CAS No. 1015484-22-6 Borate(1-), trifluoro[(4-methyl-1-piperazinyl)methyl]-, potassium (1:1), (T-4)- Catalog No.:AG0004RF MDL No.:MFCD18071161 MF:C6H13BF3KN2 MW:220.0853
CAS No. 101549-69-3 Zinc, didodecyl- Catalog No.:AG0004RZ MDL No.: MF:C24H50Zn MW:404.0338	CAS No. 101550-46-3 Dibenzoxepinone Catalog No.:AG0004RY MDL No.: MF:C14H10O2 MW:210.2280	CAS No. 101552-37-8 Methanesulfonamide, N-(3,5-dimethyl-4-nitrophenyl)- Catalog No.:AG0004RX MDL No.: MF:C9H12N2O4S MW:244.2676
CAS No. 101552-39-0 Benzonitrile, 3,5-dimethyl-4-nitro- Catalog No.:AG0004RW MDL No.: MF:C9H8N2O2 MW:176.1720	CAS No. 101553-94-0 3H-Naphtho[2,1-b]pyran-3-one, 1-(bromomethyl)- Catalog No.:AG0004RV MDL No.: MF:C14H9BrO2 MW:289.1241	CAS No. 101553-98-4 Benzenemethanol, 4-[5-(1,3-dioxan-2-yl)-2-methoxyphenoxy]- Catalog No.:AG0004RU MDL No.: MF:C18H20O5 MW:316.3484
CAS No. 101554-05-6 Benzoxazole, 2-[(4-methoxyphenyl)methyl]- Catalog No.:AG0004RT MDL No.: MF:C15H13NO2 MW:239.2692	CAS No. 101554-46-5 4(1H)-Pteridinone, 6,7-dihydro-6,7-dimethyl-, (6R-cis)- (9CI) Catalog No.:AG0004RS MDL No.: MF:C8H10N4O MW:178.1912	CAS No. 101554-56-7 1H-Tetrazole, 1-methyl-5-(methyldithio)- Catalog No.:AG0004RR MDL No.: MF:C3H6N4S2 MW:162.2365
CAS No. 101554-76-1 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, 2-nitro-4-sulfophenyl ester, sodium salt (1:1) Catalog No.:AG0004RQ MDL No.:MFCD00236937 MF:C16H16N2NaO9S MW:435.3610	CAS No. 101555-44-6 Benzothiazole, sulfate (1:1) Catalog No.:AG0004RP MDL No.: MF:C7H7NO4S2 MW:233.2648	CAS No. 101555-48-0 Disilane, 1,1,2,2-tetraiodo- Catalog No.:AG0004RO MDL No.: MF:H2I4Si2 MW:565.8048
CAS No. 101555-60-6 2-Pyrrolidineacetic acid, 1-[(1,1-dimethylethoxy)carbonyl]-, (2R)- Catalog No.:AG0004RN MDL No.:MFCD06202402 MF:C11H19NO4 MW:229.2729	CAS No. 101555-61-7 Benzenebutanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-, (βR)- Catalog No.:AG0004RM MDL No.:MFCD01076270 MF:C15H21NO4 MW:279.3315	CAS No. 101555-62-8 1,2-Pyrrolidinedicarboxylic acid, 1-(9H-fluoren-9-ylmethyl) ester, (2R)- Catalog No.:AG0004RL MDL No.:MFCD00077067 MF:C20H18NO4- MW:336.3612
CAS No. 101555-63-9 1,2-Piperidinedicarboxylic acid, 1-(9H-fluoren-9-ylmethyl) ester, (2R)- Catalog No.:AG0004RK MDL No.:MFCD00235899 MF:C21H20NO4- MW:350.3878	CAS No. 101558-59-2 Pyridinium, 4-benzoyl-1-methyl- Catalog No.:AG0004RJ MDL No.: MF:C13H12NO+ MW:198.2405	CAS No. 101558-72-9 Morpholine, 4-[2-(2-bromophenoxy)ethyl]- Catalog No.:AG0004RI MDL No.:MFCD01308474 MF:C12H16BrNO2 MW:286.1649