Synthesis and Reactions of a 2(5H)-Furanone Bearing Two Furyl Substituents

Ahmed I. Hashem,a Wael S. I. Abou-Elmagd,a* Eman A. El-Bordany,a and Ahmed Abdel Azizb

Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt b
Fire and Explosive Department, Egyptian Criminal Lab, Cairo, Egypt
*E-mail: waelmagd97@yahoo.com
Received April 25, 2018
DOI 10.1002/jhet.3398
Published online 19 November 2018 in Wiley Online Library (wileyonlinelibrary.com).

 

INTRODUCTION
2(5H)-Furanones represent a group of heterocyclic compounds of synthetic and biological importance [1–3]. The chemistry compounds had been reviewed by one of us [4]. The 2(5H)-furanone nucleus is present in a wide variety of biologically active natural products. Some of these derivatives have medicinal importance; thus, Rofecoxib (A) was proved to have good efficiency in animal models of
inflammation and effective clinical efficacy in both dental pain and osteoarthritis [5]. Furthermore, the 2(5H) furanone (B) was considered as the most selective Cox-2 inhibitor reported. Its high selectivity
makes this compound potentially very useful in chromic dosing situation [6].

In a previous investigation [7], we studied the reaction of benzoin 1a with ethyl cyanoacetate in sodium ethoxide/ethanol. The reaction was found to give a mixture of 3-cyano-4,5-diphenyl-2(5H)-furanone 2a in 85% yield and its isomeric product, namely, 3-cyano-4,5-diphenyl-2(3H)-furanone 3 in 15% yield (Scheme 1).

 

The formation of 3 was explained on the basis of isomerization of 2a in the presence of the strong base (ethoxide ion). Such isomerization might involve the intermediacy of carbanions (C) and (D), which are
stabilized by the phenyl group at position-5 and the cyano group at position-3 (Scheme 2). It was of interest to the authors to reinvestigate this reaction using furoin 1b instead of benzoin 1a by carrying
out the reaction under the same conditions.

 

RESULTS AND DISCUSSION
The 2(5H)-furanone, namely, 3-cyano-4,5-di(furyl-2-yl)-2(5H)-furanone 2b, was formed as the only isolable product, without the formation of its 2(3H)-isomeric product when the furoin 1b was allowed to react with ethyl cyanoacetate in sodium ethoxide/ethanol mixture. We believe that the unfavored formation of the 2(3H)-isomer may be attributed to the fact that the furyl group at position-5, compared with the phenyl group, is not capable of stabilizing the carbanion intermediate (C) (cf. Scheme 2). This behavior may be explained on the basis that (i) the resonance energy of the furan nucleus is
16 kcal/mol, a value that is much smaller than that of the benzene ring (35.9) kcal/mol, and (ii) the furane ring is known to be a л electron donor and a σ-electron acceptor [8]. The structure of 2b was substantiated from its spectral data. Thus, the IR spectrum shows appearance of absorption of C=O group of lactone at 1769 cm1 and the appearance of an absorption of CN group at 2233 cm1. The assigned structure is supported from 1 H-NMR and mass spectra (cf. experimental part).

The study was extended to explore the behavior of the synthesized 2(5H)-furanone 2b toward some nitrogen nucleophiles. Thus, when the 2(5H)-furanone 2b was refluxed with hydrazine hydrate in ethanol, the acid hydrazide derivative 4 was obtained (Scheme 3). The formation of 4 may be explained on the basis of isomerization of the 2(5H)-furanone 2b to its 2(3H)-isomer (not isolated), followed by ring opening to give the open chain hydrazide 4. The structure of 4 was illustrated from its analytical as well as spectral data. The IR spectrum showed disappearance of absorption of C=O group of the lactone and the appearance of the absorption of hydrazino group at 3100, 3200, and 3270 cm1 beside ketonic and amidic C=O groups at 1735 and 1665 cm1, respectively. On the other hand, the reaction of the
furanone 2b with benzylamine in refluxing ethanol gave the benzylamide derivative 5. This behavior again indicates that under these conditions, the 2(5H)-isomer 2b isomerized firstly to its 2(3H)-tautomer before ring opening by benzylamine (Scheme 4). On fusion of the furanone 2b with benzylamine in neat, the pyrrolone derivative 6 was obtained as the only isolable product.

 

The reaction of the furanone 2b with ammonium acetate was also tried. On refluxing 2b with ammonium acetate in acetic acid, the reaction gave the hydroxy pyrrole derivative 7. The presence of cyano group at position-3 initiated our interest to construct a thiazolidinone ring at this position. Thus, 2b was allowed to react with thioglycolic acid to give the hydroxy thiazole derivative 8 (Scheme 3). The structures of all the products obtained were elucidated from their analytical as well as spectral analyses (cf. experimental part).

 

The presence of acid hydrazide group in compound 4 promoted our interest to construct some nitrogen containing heterocycles. Thus, treatment of the acid hydrazide derivative 4 with acetonylacetone in refluxing ethanol/dioxane mixture afforded the pyrrolylpyrrole derivative 9 (Scheme 5). The structure of compound 9 was substantiated from its analytical and spectral data. The IR spectrum showed the disappearance of NH2 and NH bands. Further support for its structure was gained from its 1 H-NMR and mass spectra (cf. experimental part). The mechanistic pathway for the formation of the pyrrolylpyrrole derivative 9 is represented by Scheme 6.

 

The hydroxypyrrole derivative 10 was obtained upon treatment of the acid hydrazide derivative 4 with acetylacetone in refluxing ethanol/AcOH mixture. Treatment of an ethanolic solution of the acid hydrazide derivative 4 with ethyl acetoacetate afforded the hydroxypyrazole derivative 11. The IR spectrum of 11 exhibits band corresponding to OH at 3205 cm1 (br.) and the disappearance of the carbonyl groups. Fusion of 4 with ethyl cinnamate afforded the Michael adduct followed by cyclization to form the pyrazolopyridazinone derivative 12. The IR spectrum of 12 exhibits bands corresponding to the carbonyls vibrational coupling at 1712 and 1695 cm1. The mechanistic pathway for the formation of the pyrazolopyridazinone derivative 12 is represented in (Scheme 7).

 

On the other hand, when the acid hydrazide derivative 4 was allowed to react with diethylmalonate, the pyrazolidinone derivative 13 was obtained. Inspection of the 1 H-NMR spectrum of compound 13 revealed its existence as lactam–lactim tautomer. Thus, the 1 H-NMR shows two singlet signals for CH2 at δ 2.98 and 3.17 ppm corresponding to lactam–lactim mixture, respectively, beside two broad singlet for OH and amide NH groups at δ 13.31 and 10.72 ppm, respectively. Further support for the structure of compounds 9–13 was gained from 1 H-NMR and their mass spectra, which showed the correct molecular ion peaks beside some abundance peaks (cf. experimental part).

 

The N-phthalimide derivative 14 was obtained upon treatment of the acid hydrazide derivative 4 with phthalic anhydride (Scheme 8). The structure of compound 14 was illustrated from its analytical and spectral data. Inspection of the IR and the 1 H-NMR spectra of compound 14 revealed its existence as mixture of ketoenol tautomers. The IR spectrum exhibits broad band characteristic of the OH group of enol form at 3420 cm1 beside the vibrational coupling bands of the carbonyl groups at 1744 and 1724 cm1. The 1 H-NMR shows singlet signal corresponding to the CH of keto-form at δ 3.55 ppm and signal for OH at δ 8.81 ppm corresponding to the enol-form. Refluxing the acid hydrazide derivative 4 with 1-bromononane in dry DMF afforded the pyridazinone derivative 15. The formation of 15 can be explained by nucleophilic substitution reaction between the acid hydrazide and the alkyl halide followed by cyclization. On the other hand, treatment of the acid hydrazide derivative 4 with benzil gave the hydrazone derivative 16. Inspection of the 1 H-NMR spectrum of compound 16 revealed its existence as a mixture of syn/anti-stereoisomers in the ratio of 3:2, respectively, based on the appearance of two
singlets for CH proton (cf. experimental part).

 

Treatment of the acid hydrazide derivative 4 with 4-methoxybenzaldehyde gave the Schiff base product 17. Inspection of the 1 H-NMR spectrum of compound 17 revealed its existence as a mixture of syn/antistereoisomers in the ratio of 1:5, respectively, based on the appearance of two singlets for =CH and two singlets for OCH3 protons (cf. experimental part). The hydrazone derivative 17 obtained in the previous step was treated with thioglycolic acid to give the thiazolidinone derivative 18 (Scheme 8). The structures of compounds 14–18 were ascertained from their microanalytical and spectral data (cf. experimental part).

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CAS No. 101084-51-9 6-Benzothiazolecarboxamide Catalog No.:AG0003PE MDL No.:MFCD11643189 MF:C8H6N2OS MW:178.2110	CAS No. 101084-52-0 5(4H)-Isoxazolone, 3-(4-pyridinyl)- Catalog No.:AG0003PD MDL No.:MFCD01936026 MF:C8H6N2O2 MW:162.1454	CAS No. 101084-60-0 2(3H)-Benzoxazolone, 3-methyl-5-nitro- Catalog No.:AG0003PC MDL No.:MFCD19375109 MF:C8H6N2O4 MW:194.1442
CAS No. 101084-76-8 Boronic acid, B-(4-bromo-3-thienyl)- Catalog No.:AG0003PB MDL No.:MFCD06801663 MF:C4H4BBrO2S MW:206.8534	CAS No. 101084-77-9 3-Pyridinesulfinic acid Catalog No.:AG0003PA MDL No.:MFCD18384596 MF:C5H5NO2S MW:143.1637	CAS No. 101084-78-0 4-Pyridinesulfinic acid Catalog No.:AG0003P9 MDL No.: MF:C5H5NO2S MW:143.1637
CAS No. 101084-81-5 Benzoic acid, 3-borono-5-nitro- Catalog No.:AG0003P8 MDL No.:MFCD00757433 MF:C7H6BNO6 MW:210.9366	CAS No. 101084-82-6 Benzene, 4-bromo-2-chloro-1-(methylthio)- Catalog No.:AG0003QG MDL No.:MFCD22543648 MF:C7H6BrClS MW:237.5445	CAS No. 101084-86-0 Benzenemethanamine, 2,3,5-trichloro- Catalog No.:AG0003QF MDL No.: MF:C7H6Cl3N MW:210.4882
CAS No. 101084-94-0 5(4H)-Isoxazolone, 3-(3-pyridinyl)- Catalog No.:AG0003QE MDL No.:MFCD21334968 MF:C8H6N2O2 MW:162.1454	CAS No. 101084-95-1 5-Benzothiazolecarboxylic acid, 2-amino- Catalog No.:AG0003QD MDL No.:MFCD00160079 MF:C8H6N2O2S MW:194.2104	CAS No. 101084-96-2 Benzonitrile, 2-methoxy-4-nitro- Catalog No.:AG0003QC MDL No.:MFCD02093781 MF:C8H6N2O3 MW:178.1448
CAS No. 1010840-17-1 1,3,2-Dioxaborolane, 2,2'-(1,2-ethynediyl)bis[4,4,5,5-tetramethyl- Catalog No.:AG0003PU MDL No.:MFCD22666429 MF:C14H24B2O4 MW:277.9600	CAS No. 101085-03-4 Benzoic acid, 2-bromo-4-hydroxy-, methyl ester Catalog No.:AG0003QB MDL No.: MF:C8H7BrO3 MW:231.0434	CAS No. 101085-21-6 2-Propenamide, 3-(4-bromophenyl)-2-cyano- Catalog No.:AG0003QA MDL No.: MF:C10H7BrN2O MW:251.0794
CAS No. 101085-25-0 Oxazole, 5-bromo-4-(bromomethyl)-2-phenyl- Catalog No.:AG0003Q9 MDL No.: MF:C10H7Br2NO MW:316.9767	CAS No. 101087-11-0 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-butyl-5-[2-(1-piperidinyl)ethyl]- Catalog No.:AG0003Q8 MDL No.: MF:C15H25N3O3 MW:295.3773	CAS No. 101089-40-1 Ethanone, 1-phenyl-2-[(phenylmethyl)amino]-, hydrochloride (1:1) Catalog No.:AG0003Q7 MDL No.: MF:C15H16ClNO MW:261.7466
CAS No. 101089-45-6 2H-1,3-Benzoxazine, 3,4-dihydro-6-methyl-3-phenyl- Catalog No.:AG0003Q6 MDL No.: MF:C15H15NO MW:225.2857	CAS No. 101089-46-7 1-Butanone, 1-phenyl-4-(4-pyridinyl)- Catalog No.:AG0003Q5 MDL No.: MF:C15H15NO MW:225.2857	CAS No. 101089-51-4 9H-Fluoren-9-ol, 2-(dimethylamino)- Catalog No.:AG0003Q4 MDL No.: MF:C15H15NO MW:225.2857
CAS No. 101089-63-8 Carbamothioic acid, N-phenyl-, O-(2-phenylethyl) ester Catalog No.:AG0003Q3 MDL No.: MF:C15H15NOS MW:257.3507	CAS No. 1010898-45-9 3-Pyridinecarbonitrile, 1,2-dihydro-1-(2-methoxyethyl)-4,6-dimethyl-2-oxo- Catalog No.:AG0003PT MDL No.:MFCD12200747 MF:C11H14N2O2 MW:206.2411	CAS No. 10109-95-2 1,4-Benzenedicarboxylic acid, 2,5-bis(phenylamino)- Catalog No.:AG0003QH MDL No.: MF:C20H16N2O4 MW:348.3520
CAS No. 101091-29-6 Hydrazinecarbothioamide, 2-[[4-(phenylmethoxy)phenyl]methylene]- Catalog No.:AG0003Q2 MDL No.: MF:C15H15N3OS MW:285.3641	CAS No. 101091-67-2 Urea, N-ethyl-N'-(4-nitrophenyl)-N-phenyl- Catalog No.:AG0003Q1 MDL No.: MF:C15H15N3O3 MW:285.2979	CAS No. 101092-03-9 2-Pteridinamine, 6,7-dimethyl-4-(phenylmethoxy)- Catalog No.:AG0003Q0 MDL No.: MF:C15H15N5O MW:281.3125
CAS No. 101093-37-2 Benzenemethanol, 4-(2-phenylethenyl)- Catalog No.:AG0003PZ MDL No.: MF:C15H14O MW:210.2711	CAS No. 101093-56-5 Benzaldehyde, 2-methyl-4-(phenylmethoxy)- Catalog No.:AG0003PY MDL No.:MFCD01317809 MF:C15H14O2 MW:226.2705	CAS No. 101093-66-7 Benzene, 1-methyl-4-[2-(phenylsulfonyl)ethenyl]- Catalog No.:AG0003PX MDL No.: MF:C15H14O2S MW:258.3355
CAS No. 101093-81-6 1-Naphthaleneacetic acid, 4-methyl-α-oxo-, ethyl ester Catalog No.:AG0003PW MDL No.:MFCD09801435 MF:C15H14O3 MW:242.2699	CAS No. 101093-83-8 Benzoic acid, 2-[[(4-methoxyphenyl)methyl]thio]- Catalog No.:AG0003PV MDL No.: MF:C15H14O3S MW:274.3349	CAS No. 101093-93-0 Benzoic acid, 2-(2-phenoxyethoxy)- Catalog No.:AG0003QU MDL No.:MFCD02724891 MF:C15H14O4 MW:258.2693
CAS No. 101094-57-9 Indolizine, 1-(4-chlorophenyl)- Catalog No.:AG0003QT MDL No.: MF:C14H10ClN MW:227.6889	CAS No. 101094-85-3 Phthalazine, 1-chloro-4-(4-pyridinylmethyl)- Catalog No.:AG0003QS MDL No.:MFCD00631940 MF:C14H10ClN3 MW:255.7023	CAS No. 101095-61-8 Benzene, 1-(chloromethyl)-4-(2-phenylethenyl)- Catalog No.:AG0003QR MDL No.: MF:C15H13Cl MW:228.7167
CAS No. 101095-67-4 Urea, N-(4-acetylphenyl)-N'-(4-chlorophenyl)- Catalog No.:AG0003QQ MDL No.: MF:C15H13ClN2O2 MW:288.7289	CAS No. 101096-01-9 Benzene, 1-(1-chloro-2-phenylethenyl)-4-methoxy- Catalog No.:AG0003QP MDL No.: MF:C15H13ClO MW:244.7161	CAS No. 101096-64-4 Ethanone, 1-[2-hydroxy-3-iodo-4-(phenylmethoxy)phenyl]- Catalog No.:AG0003QO MDL No.: MF:C15H13IO3 MW:368.1664
CAS No. 101096-72-4 Benzeneacetonitrile, 4-(phenylmethyl)- Catalog No.:AG0003QN MDL No.:MFCD00060310 MF:C15H13N MW:207.2704	CAS No. 101096-81-5 2-Propenamide, 3-[1,1'-biphenyl]-4-yl- Catalog No.:AG0003QM MDL No.: MF:C15H13NO MW:223.2698	CAS No. 101097-11-4 2-(2-Methoxyphenyl)-5-methylbenzo[d]oxazole Catalog No.:AG0003QL MDL No.: MF:C15H13NO2 MW:239.2692
CAS No. 101097-45-4 Benzoic acid, 4-(aminocarbonyl)-, phenylmethyl ester Catalog No.:AG0003QK MDL No.: MF:C15H13NO3 MW:255.2686	CAS No. 101098-71-9 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(3,7-dimethyloctyl)- Catalog No.:AG0003QJ MDL No.: MF:C14H24N2O3 MW:268.3520	CAS No. 101099-24-5 Furan, 2,5-bis(butoxymethyl)- Catalog No.:AG0003QI MDL No.: MF:C14H24O3 MW:240.3386
CAS No. 1011-10-5 4,7(3H,6H)-Pteridinedione, 2-amino-5,8-dihydro- Catalog No.:AG0003R6 MDL No.: MF:C6H7N5O2 MW:181.1521	CAS No. 1011-12-7 Cyclohexanone, 2-cyclohexylidene- Catalog No.:AG0003R5 MDL No.:MFCD19443386 MF:C12H18O MW:178.2707	CAS No. 1011-13-8 Piperazine, 1-(2-bromophenyl)- Catalog No.:AG0003R4 MDL No.:MFCD03844726 MF:C10H13BrN2 MW:241.1276
CAS No. 1011-15-0 Piperazine, 1-(2-fluorophenyl)- Catalog No.:AG0003R3 MDL No.:MFCD00040726 MF:C10H13FN2 MW:180.2220	CAS No. 1011-16-1 Piperazine, 1-(2-fluorophenyl)-, hydrochloride (1:1) Catalog No.:AG0003R2 MDL No.:MFCD00134409 MF:C10H14ClFN2 MW:216.6830	CAS No. 1011-17-2 Phenol, 2-(1-piperazinyl)- Catalog No.:AG0003R1 MDL No.:MFCD00190246 MF:C10H14N2O MW:178.2310
CAS No. 1011-19-4 Pyridine, 2-(1-piperidinyl)-, 1-oxide Catalog No.:AG0003R0 MDL No.:MFCD00234673 MF:C10H14N2O MW:178.2310	CAS No. 1011-24-1 4(3H)-Quinazolinone, 2-methoxy- Catalog No.:AG0003QZ MDL No.:MFCD00126781 MF:C9H8N2O2 MW:176.1720	CAS No. 1011-26-3 1-Butanone, 2-bromo-1-(4-chlorophenyl)- Catalog No.:AG0003QY MDL No.:MFCD12031566 MF:C10H10BrClO MW:261.5428
CAS No. 1011-27-4 Benzaldehyde, 3,5-dimethoxy-4-methyl- Catalog No.:AG0003QX MDL No.: MF:C10H12O3 MW:180.2005	CAS No. 1011-37-6 Isoxazole, 5-(chloromethyl)-3-phenyl- Catalog No.:AG0003QW MDL No.:MFCD01935949 MF:C10H8ClNO MW:193.6296	CAS No. 1011-38-7 5-Isoxazolecarbonitrile, 4,5-dihydro-3-phenyl- Catalog No.:AG0003QV MDL No.: MF:C10H8N2O MW:172.1833
CAS No. 1011-39-8 5-Isoxazolecarbonitrile, 3-phenyl- Catalog No.:AG0003RU MDL No.: MF:C10H6N2O MW:170.1674	CAS No. 1011-40-1 5-Thiazolecarboxaldehyde, 2-phenyl- Catalog No.:AG0003RT MDL No.:MFCD04973719 MF:C10H7NOS MW:189.2337	CAS No. 1011-41-2 5-Thiazolecarboxaldehyde, 2-(4-morpholinyl)- Catalog No.:AG0003RS MDL No.:MFCD01568825 MF:C8H10N2O2S MW:198.2422
CAS No. 1011-42-3 7-Isoquinolinol, 1,2,3,4-tetrahydro-6-methoxy- Catalog No.:AG0003RR MDL No.: MF:C10H13NO2 MW:179.2157	CAS No. 1011-46-7 3(2H)-Pyridazinone, 4,5-dihydro-6-phenyl- Catalog No.:AG0003RQ MDL No.:MFCD00099597 MF:C10H10N2O MW:174.1992	CAS No. 1011-47-8 Ethanone, 1-(2-quinolinyl)- Catalog No.:AG0003RP MDL No.:MFCD08062664 MF:C11H9NO MW:171.1953
CAS No. 1011-48-9 Ethanone, 1-(2,3-dihydro-1,4-benzodioxin-2-yl)- Catalog No.:AG0003RO MDL No.:MFCD00457680 MF:C10H10O3 MW:178.1846	CAS No. 1011-49-0 1H-Indole, 2-ethoxy-1-methyl- Catalog No.:AG0003RN MDL No.:MFCD01463480 MF:C11H13NO MW:175.2270	CAS No. 1011-50-3 2-Quinolineethanol Catalog No.:AG0003RM MDL No.:MFCD01685503 MF:C11H11NO MW:173.2111
CAS No. 1011-51-4 Oxazole, 5-(4-methoxyphenyl)- Catalog No.:AG0003RL MDL No.:MFCD00085108 MF:C10H9NO2 MW:175.1840	CAS No. 1011-59-2 Benzenepropanamine, γ-chloro-N,N-dimethyl-, hydrochloride (1:1) Catalog No.:AG0003RK MDL No.:MFCD04114488 MF:C11H17Cl2N MW:234.1654	CAS No. 1011-60-5 Benzenebutanoic acid, γ-amino- Catalog No.:AG0003RJ MDL No.:MFCD00844723 MF:C10H13NO2 MW:179.2157
CAS No. 1011-61-6 1,5-Pentanediol, 1-phenyl- Catalog No.:AG0003RI MDL No.: MF:C11H16O2 MW:180.2435	CAS No. 1011-65-0 1H-Indole-5-carboxylic acid, methyl ester Catalog No.:AG0003RH MDL No.:MFCD00153023 MF:C10H9NO2 MW:175.1840	CAS No. 1011-74-1 Benzenemethanol, α-(aminomethyl)-4-hydroxy-3-methoxy-, hydrochloride (1:1) Catalog No.:AG0003RF MDL No.:MFCD00012882 MF:C9H14ClNO3 MW:219.6654
CAS No. 1011-84-3 Benzenecarboximidoyl chloride, N-hydroxy-4-nitro- Catalog No.:AG0003RE MDL No.:MFCD01878547 MF:C7H5ClN2O3 MW:200.5792	CAS No. 1011-85-4 1,4-Cyclohexanedicarboxylic acid, 1-methyl ester, cis- Catalog No.:AG0003RD MDL No.:MFCD01311246 MF:C9H13O4- MW:185.1971	CAS No. 1011-92-3 2-Propenoic acid, 2-cyano-3-phenyl- Catalog No.:AG0003RC MDL No.:MFCD00016813 MF:C10H7NO2 MW:173.1681
CAS No. 1011-95-6 Stannane, diphenyl- Catalog No.:AG0003RB MDL No.: MF:C12H12Sn MW:274.9247	CAS No. 101102-31-2 1,3,5-Triazine, 2-hydrazinyl-4,6-diphenoxy- Catalog No.:AG0003R9 MDL No.: MF:C15H13N5O2 MW:295.2960	CAS No. 101102-36-7 Acetamide, N-[4-[[2-(2,4-dinitrophenyl)hydrazinylidene]methyl]phenyl]- Catalog No.:AG0003R8 MDL No.: MF:C15H13N5O5 MW:343.2942
CAS No. 101105-22-0 2,5-Pyrrolidinedione, 1-butyl-3-(phenylmethyl)- Catalog No.:AG0003R7 MDL No.: MF:C15H19NO2 MW:245.3169	CAS No. 10111-08-7 1H-imidazole-2-carbaldehyde Catalog No.:AG0003RA MDL No.:MFCD00003544 MF:C4H4N2O MW:96.0874	CAS No. 10111-14-5 Phosphonium, 1,4-phenylenebis[triphenyl-, dibromide (9CI) Catalog No.:AG0003SJ MDL No.: MF:C42H34Br2P2 MW:760.4749
CAS No. 10111-23-6 Phosphonium, (4-methylphenyl)triphenyl-, iodide (1:1) Catalog No.:AG0003SI MDL No.: MF:C25H22IP MW:480.3204	CAS No. 10111-76-9 Ethanethioic acid, S-2-pyridinyl ester Catalog No.:AG0003SH MDL No.: MF:C7H7NOS MW:153.2016	CAS No. 101110-06-9 3(2H)-Furanone, dihydro-2,2-diphenyl- Catalog No.:AG0003SB MDL No.: MF:C16H14O2 MW:238.2812
CAS No. 101110-21-8 5-Acenaphthyleneacetic acid, 1,2-dihydro-α-oxo-, ethyl ester Catalog No.:AG0003SA MDL No.:MFCD09801382 MF:C16H14O3 MW:254.2806	CAS No. 101110-68-3 Methanone, [2-hydroxy-4-(1-oxopropoxy)phenyl]phenyl- Catalog No.:AG0003S9 MDL No.: MF:C16H14O4 MW:270.2800	CAS No. 101111-39-1 Phosphonic acid, P-2-propen-1-yl-, diphenyl ester Catalog No.:AG0003S8 MDL No.: MF:C15H15O3P MW:274.2516
CAS No. 101111-62-0 Propanamide, 2-chloro-N-ethyl-N-1-naphthalenyl- Catalog No.:AG0003S7 MDL No.:MFCD06359999 MF:C15H16ClNO MW:261.7466	CAS No. 101112-61-2 1H-Pyrido[3,4-b]indole, 2,9-diacetyl-2,3,4,9-tetrahydro- (6CI,9CI) Catalog No.:AG0003S6 MDL No.: MF:C15H16N2O2 MW:256.2997	CAS No. 101113-14-8 4H-Quinolizine-1,3-dicarboxylic acid, 4-imino-, 1,3-diethyl ester Catalog No.:AG0003S5 MDL No.: MF:C15H16N2O4 MW:288.2985
CAS No. 101113-66-0 Acetamide, N-ethyl-N-(1,2,3,4-tetrahydro-2-naphthalenyl)- Catalog No.:AG0003S4 MDL No.: MF:C14H19NO MW:217.3068	CAS No. 101113-74-0 Butanamide, N-(1,2,3,4-tetrahydro-2-naphthalenyl)- Catalog No.:AG0003S3 MDL No.: MF:C14H19NO MW:217.3068	CAS No. 101113-92-2 3-Oxa-1-azaspiro[4.5]decane, 2-phenyl- Catalog No.:AG0003S2 MDL No.: MF:C14H19NO MW:217.3068
CAS No. 101116-44-3 2H-Benzimidazol-2-one, 1,3-dihydro-1-[2-(1-piperidinyl)ethyl]- Catalog No.:AG0003S1 MDL No.: MF:C14H19N3O MW:245.3202	CAS No. 101117-48-0 4H-Imidazol-4-one, 3-amino-3,5-dihydro-2-phenyl-5-(phenylmethylene)- Catalog No.:AG0003S0 MDL No.: MF:C16H13N3O MW:263.2939	CAS No. 101119-04-4 Benzeneacetyl chloride, 3-methoxy-2-nitro-4-(phenylmethoxy)- Catalog No.:AG0003RZ MDL No.: MF:C16H14ClNO5 MW:335.7391
CAS No. 10112-09-1 Silane, (chloromethyl)- (6CI,7CI,8CI,9CI) Catalog No.:AG0003SG MDL No.: MF:CH5ClSi MW:80.5889	CAS No. 10112-11-5 Silane, (trifluoromethyl)- Catalog No.:AG0003SF MDL No.: MF:CH3F3Si MW:100.1152	CAS No. 10112-15-9 Benzenamine, N-ethyl-2-nitro- Catalog No.:AG0003SE MDL No.:MFCD00007091 MF:C8H10N2O2 MW:166.1772
CAS No. 10112-41-1 Formamide, N-(iminomethyl)- (9CI) Catalog No.:AG0003SD MDL No.: MF:C2H4N2O MW:72.0660	CAS No. 101122-64-9 1,12-Dodecanediaminium, N1,N1,N1,N12,N12,N12-hexaethyl-, bromide (1:2) Catalog No.:AG0003RY MDL No.: MF:C24H54Br2N2 MW:530.5070	CAS No. 101123-27-7 1,2-Propanediol, 3-(octadecadienyloxy)- Catalog No.:AG0003RX MDL No.: MF:C21H40O3 MW:340.5405
CAS No. 1011231-34-7 2-Pyridinecarboximidamide, 6-chloro- Catalog No.:AG0003RV MDL No.: MF:C6H6ClN3 MW:155.5849	CAS No. 101125-08-0 Spiro[1H-isoindole-1,2'-[2H]thiet]-3(2H)-one, 2-methyl-3',4'-diphenyl- Catalog No.:AG0003RW MDL No.: MF:C23H17NOS MW:355.4522	CAS No. 1011257-42-3 Phosphinic acid, P,P-diphenyl-, copper(1+) salt (1:1) Catalog No.:AG0003SO MDL No.:MFCD09702021 MF:C12H10CuO2P MW:280.7264
CAS No. 1011263-90-3 4-Pyridinecarboxylic acid, 2,6-dimethyl-, 1,1-dimethylethyl ester Catalog No.:AG0003SN MDL No.: MF:C12H17NO2 MW:207.2689	CAS No. 1011264-05-3 4-Pyridinecarboxylic acid, 2-ethoxy-6-methyl- Catalog No.:AG0003SM MDL No.: MF:C9H11NO3 MW:181.1885	CAS No. 101128-42-1 Benzeneacetic acid, α-oxo-, 2,2-dimethylpropyl ester Catalog No.:AG0003SS MDL No.: MF:C13H16O3 MW:220.2643
CAS No. 101128-56-7 4,7-Methano-1H-indenecarboxaldehyde, octahydro-5-methoxy- Catalog No.:AG0003SR MDL No.: MF:C12H18O2 MW:194.2701	CAS No. 1011291-78-3 Phthalazine, 7-bromo-1-chloro- Catalog No.:AG0003SL MDL No.:MFCD13190050 MF:C8H4BrClN2 MW:243.4878	CAS No. 1011296-64-2 1,4-Dioxaspiro[4.5]decane, 8-(2-iodoethyl)- Catalog No.:AG0003SK MDL No.: MF:C10H17IO2 MW:296.1453
CAS No. 101130-32-9 [1]Benzothieno[2,3-d]pyrimidine, 4-chloro-5,6,7,8-tetrahydro-2-(2-phenylethenyl)-, (E)- (9CI) Catalog No.:AG0003SQ MDL No.: MF:C18H15ClN2S MW:326.8431