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Alkynylation of Carbon Radicals

EBX reagents are highly useful for the functionalization of carbon and heteroatom nucleophiles, as well as organometallic intermediates. The functionalization of radicals, which can be generated under neutral conditions, constitutes a further interesting area of applications. Li and co-workers were the first to report a decarboxylative alkynylation of carboxylic acids using EBX reagents and strong oxidants.49 In 2015, we developed milder conditions for the synthesis of alkynes 36a−f based on photoredox catalysis to avoid strong oxidants (Scheme 23).50 Xiao and co-workers reported a similar transformation simultaneously.

A mechanism for the decarboxylative alkynylation was proposed based on both experimental and computational studies (Scheme 24).52 Single-electron oxidation of the carboxylate by the excited state of the Ir(III)-catalyst generates radical I after extrusion of CO2. Addition to EBX then delivers the desired product and iodo radical II, which can then be reduced by Ir(II) to close the catalytic cycle. Concerning the radical addition step, two mechanisms very close in energy were proposed based on DFT calculations: a concerted α-addition via III or a β-addition via IV.

In 2018, we reported the alkynylation of nitrile-substituted alkyl radicals generated via oxidative ring fragmentation of cyclic oxime ethers (Scheme 25).53 The use of organic dye 38c with an increased reduction potential in the excited state compared to 4CzIPN (38a) led to the efficient fragmentation of both 4- and 5-membered cyclic oxime ethers to give the corresponding alkynylnitriles (39a−f). The reaction probably starts with the oxidation of the carboxylate by the excited photocatalyst. Fast decarboxylation followed by acetone extrusion leads to an imine radical. Fragmentation to an alkyl radical followed by alkynylation then gives the product.

ELECTROPHILIC AZIDATION
Azides, as alkynes, are versatile functional groups, which are usually introduced as nucleophiles. Electrophilic azide sources allow other disconnections. Noncyclic azide hypervalent iodine reagents are not stable and need to be prepared in situ. An important progress was realized when stable cyclic ABXs were introduced by Zhdankin and co-workers.9 Nevertheless, new synthetic applications emerged only in 2013, with the independent reports of Gade and co-workers,54 our group,55 and Studer and co-workers.56 Since then, the field is in full expansion.

Azidation of β-Keto Esters and Silyl Enol Ethers
In 2013, we investigated the azidation of ketoester-derived enolates with ABXs as a proof-of-concept transformation. Such azidation had been realized with other hypervalent iodine reagents,57 but had not been reported with ABXs when we started our investigations. A metal free protocol for cyclic indanones was developed using azidobenziodoxole 40 (41a−c, Scheme 26).55 However, less reactive substrates such as silyl enol ethers and noncyclic keto esters did not react with 40. In this case, activation of the reagent with zinc triflate as catalyst was necessary to give products 42a−d. In parallel to our work, Gade and co-workers reported an efficient enantioselective azidation of ketoesters using reagent 40.

We then reinvestigated the Tsuji−Trost approach on allyl β- keto esters (Scheme 27). Homoallylic azides 43a−c were obtained in good yields and excellent enantioselectivities. Staudinger reduction and 1,3 cycloaddition gave then homoallylic amine 44 and triazole 45.

Generation of Azido Radicals: Azido-Lactonization and Ring Expansion
In 2017, our group became interested in using azidobenziodoxol(on)es reagents for the azido-lactonization of styrene derivatives in the context of extending the olefin functionalization reactions developed with oxyalkynylation (Scheme 28).59 Photoredox activation of ABX 46 (Zhdankin reagent)9 resulted in formation of an azido radical,56,60 which reacted with the styrenes to form 1,2-azidolactones 47a−d. No radical was formed from the weaker oxidizing 40. In this case, the use of Pd(hfacac)2 as Lewis acid gave 1,1-azidolactones 48a−d, probably via a iodination, 1,2-aryl shift, azidation sequence, highlighting again the possibility to finely tune the reactivity of EBX reagents.

Following an accident due to the explosion of a sample of ABX 46, we investigated its safety profile in collaboration with a specialized company, and discovered that it is both shock and friction sensitive.61 However, the more stable azidobenziodazole 49 (ABZ) could also be used for the generation of radicals under photoredox conditions in a new ring-expansion process to give cyclopentanones 50a−d (Scheme 29), as well as in reported azidative transformations.

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CAS No. 101882-87-5 Octadecanedioic acid, 1,18-dihydrazide Catalog No.:AG0005TT MDL No.: MF:C18H38N4O2 MW:342.5199	CAS No. 101882-93-3 Dodecane, 1-(2-butoxyethoxy)- Catalog No.:AG0005TS MDL No.: MF:C18H38O2 MW:286.4931	CAS No. 101882-94-4 Dodecane, 1-[2-(2-methylpropoxy)ethoxy]- Catalog No.:AG0005TR MDL No.: MF:C18H38O2 MW:286.4931
CAS No. 101882-99-9 Decane, 1-[2-(2-butoxyethoxy)ethoxy]- Catalog No.:AG0005TQ MDL No.: MF:C18H38O3 MW:302.4925	CAS No. 1018826-44-2 Methanone, (4-methyl-1-piperazinyl)-4-piperidinyl-, hydrochloride (1:1) Catalog No.:AG0005TL MDL No.:MFCD09972278 MF:C11H22ClN3O MW:247.7649	CAS No. 1018826-73-7 Pyridine, 3-[1-(phenylmethyl)-4-piperidinyl]- Catalog No.:AG0005TK MDL No.:MFCD28369450 MF:C17H20N2 MW:252.3541
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CAS No. 101891-01-4 8(5H)-Quinolinone, 5-[[4-(diethylamino)phenyl]imino]- Catalog No.:AG0005UJ MDL No.: MF:C19H19N3O MW:305.3737	CAS No. 101891-90-1 Naphthalene, 2,6-dibutoxy- Catalog No.:AG0005UI MDL No.: MF:C18H24O2 MW:272.3820	CAS No. 101894-03-5 4H-Pyran-4-one, 3,5-bis(phenylmethyl)- Catalog No.:AG0005UH MDL No.: MF:C19H16O2 MW:276.3291
CAS No. 101894-05-7 Naphthalene, 1-[2-[(4-methylphenyl)sulfonyl]ethenyl]- Catalog No.:AG0005UG MDL No.: MF:C19H16O2S MW:308.3941	CAS No. 101894-48-8 Naphthalene, 2-[(2,3-dihydro-1H-inden-2-yl)thio]- Catalog No.:AG0005UF MDL No.: MF:C19H16S MW:276.3953	CAS No. 101894-60-4 2H-1-Benzopyran-2-one, 3-[1-(4-bromophenyl)-3-oxobutyl]-4-hydroxy- Catalog No.:AG0005UE MDL No.: MF:C19H15BrO4 MW:387.2240
CAS No. 101894-98-8 1H-Indole, 3-methyl-2-(2-naphthalenyl)- Catalog No.:AG0005UD MDL No.: MF:C19H15N MW:257.3291	CAS No. 1018946-38-7 Benzofuran, 2-(3,4-dimethoxyphenyl)-5-(3-methoxypropyl)- Catalog No.:AG0005U5 MDL No.: MF:C20H22O4 MW:326.3863	CAS No. 101895-15-2 Benzoic acid, 2-([1,1'-biphenyl]-4-ylamino)- Catalog No.:AG0005UC MDL No.: MF:C19H15NO2 MW:289.3279
CAS No. 101895-37-8 Benzoic acid, 2-[[2-(1-naphthalenyl)acetyl]amino]- Catalog No.:AG0005UB MDL No.:MFCD02223149 MF:C19H15NO3 MW:305.3273	CAS No. 101895-89-0 Benzoic acid, 4-[2-[4-(phenylamino)phenyl]diazenyl]- Catalog No.:AG0005UA MDL No.: MF:C19H15N3O2 MW:317.3413	CAS No. 1018953-88-2 Thieno[3,2-c]pyridine, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Catalog No.:AG0005V4 MDL No.:MFCD15143422 MF:C13H16BNO2S MW:261.1476
CAS No. 101896-21-3 4,6-Dioxa-3,7-diaza-5-phosphanonane-1,9-diol, 3,7-bis(2-hydroxyethyl)-5-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-nonadecafluoroundecyl)oxy]-, 5-oxide (9CI) Catalog No.:AG0005V8 MDL No.: MF:C19H24F19N2O8P MW:800.3459	CAS No. 101896-22-4 4,6-Dioxa-3-aza-5-phosphaheptadecan-1-ol, 9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,17-nonadecafluoro-3-(2-hydroxyethyl)-5-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-nonadecafluoroundecyl)oxy]-, 5-oxide (9CI) Catalog No.:AG0005V7 MDL No.: MF:C26H18F38NO6P MW:1193.3373	CAS No. 101896-25-7 Phenoxazin-5-ium, 7-amino-3,6,10-triethyl-2-(ethylimino)-2,10-dihydro-, perchlorate (9CI) Catalog No.:AG0005V6 MDL No.: MF:C20H37ClN3O5 MW:434.9779
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CAS No. 101901-08-0 Pyrano[3,4-b]indole-1-acetic acid, 1-ethyl-1,3,4,9-tetrahydro-8-(1-hydroxyethyl)- Catalog No.:AG0005VP MDL No.: MF:C17H21NO4 MW:303.3529	CAS No. 101901-11-5 Acetic acid, 2-[(3,6-dioxo-1,4-cyclohexadien-1-yl)thio]-, ethyl ester Catalog No.:AG0005VO MDL No.: MF:C10H10O4S MW:226.2490	CAS No. 101901-58-0 1H-Imidazole, 2,4,5-tribromo-1-[(4-methoxyphenyl)methyl]- Catalog No.:AG0005VN MDL No.: MF:C11H9Br3N2O MW:424.9140
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CAS No. 1019020-06-4 Imidazo[1,2-a]pyridine-3-carboxaldehyde, 6-fluoro- Catalog No.:AG0005WH MDL No.:MFCD09994347 MF:C8H5FN2O MW:164.1365	CAS No. 1019020-14-4 7-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde Catalog No.:AG0005WG MDL No.:MFCD09994348 MF:C8H5BrN2O MW:225.0421	CAS No. 1019021-64-7 Imidazo[1,2-a]pyridine-3-carboxylic acid, 6-methyl- Catalog No.:AG0005WF MDL No.:MFCD09994698 MF:C9H8N2O2 MW:176.1720
CAS No. 1019021-71-6 Imidazo[1,2-a]pyridine-3-carboxylic acid, 6-cyano- Catalog No.:AG0005WE MDL No.: MF:C9H5N3O2 MW:187.1549	CAS No. 1019021-78-3 Imidazo[1,2-a]pyridine-3-carboxylic acid, 6-(trifluoromethyl)- Catalog No.:AG0005WD MDL No.:MFCD09994700 MF:C9H5F3N2O2 MW:230.1434	CAS No. 1019021-85-2 Imidazo[1,2-a]pyridine-3-carboxylic acid, 6-fluoro- Catalog No.:AG0005WC MDL No.:MFCD09994701 MF:C8H5FN2O2 MW:180.1359
CAS No. 1019021-92-1 Imidazo[1,2-a]pyridine-3-carboxaldehyde, 8-fluoro- Catalog No.:AG0005WB MDL No.: MF:C8H5FN2O MW:164.1365	CAS No. 1019021-93-2 Imidazo[1,2-a]pyridine-3-carboxylic acid, 7-bromo- Catalog No.:AG0005WA MDL No.:MFCD09994702 MF:C8H5BrN2O2 MW:241.0415	CAS No. 1019024-64-6 1,2,4-Triazolo[4,3-a]pyridine-6-carbonitrile Catalog No.:AG0005W9 MDL No.:MFCD09994414 MF:C7H4N4 MW:144.1335
CAS No. 1019029-68-5 Imidazo[1,2-c]pyrimidine-2-carboxaldehyde Catalog No.:AG0005W8 MDL No.: MF:C7H5N3O MW:147.1341	CAS No. 1019030-08-0 Imidazo[1,2-a]pyrazine-2-methanamine Catalog No.:AG0005W7 MDL No.: MF:C7H8N4 MW:148.1652	CAS No. 101904-42-1 Adenosine, 8-(hydroxymethyl)- (9CI) Catalog No.:AG0005WU MDL No.: MF:C11H15N5O5 MW:297.2673
CAS No. 101904-51-2 3-Acridinecarboxylic acid, 9,10-dihydro-9-oxo-2-(phenylamino)- Catalog No.:AG0005WT MDL No.: MF:C20H14N2O3 MW:330.3368	CAS No. 101904-53-4 9(10H)-Acridinone, 2-methyl-7-[(4-methylphenyl)amino]- Catalog No.:AG0005WS MDL No.: MF:C21H18N2O MW:314.3804	CAS No. 101904-56-7 Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-yl)- Catalog No.:AG0005WR MDL No.: MF:C20H21N MW:275.3874
CAS No. 101904-93-2 1-Dodecanaminium, N,N,N-trimethyl-, methanesulfonate (1:1) Catalog No.:AG0005WQ MDL No.: MF:C16H37NO3S MW:323.5349	CAS No. 101904-95-4 1-Hexadecanaminium, N-ethyl-N,N-dimethyl-, benzenesulfonate (1:1) Catalog No.:AG0005WP MDL No.: MF:C26H49NO3S MW:455.7372	CAS No. 101905-24-2 Benzoic acid, 4-chloro-, (4-nitrobenzoyl)azanyl ester Catalog No.:AG0005WO MDL No.: MF:C14H9ClN2O5 MW:320.6847
CAS No. 101905-71-9 Benzoic acid, 2-(dimethylamino)-5-nitro-, methyl ester Catalog No.:AG0005WN MDL No.: MF:C10H12N2O4 MW:224.2133	CAS No. 1019056-31-5 5H-Pyrrolo[3,2-d]pyrimidine-7-carboxylic acid, 4-chloro- Catalog No.:AG0005W6 MDL No.:MFCD09999221 MF:C7H4ClN3O2 MW:197.5786	CAS No. 101906-05-2 Ethanone, 2,2-dihydroxy-1-[4-(trifluoromethyl)phenyl]- Catalog No.:AG0005WM MDL No.:MFCD05664098 MF:C9H7F3O3 MW:220.1453
CAS No. 101906-15-4 5-Hexen-3-ol, 5-methyl-1-(phenylmethoxy)-, (3R)- Catalog No.:AG0005WL MDL No.: MF:C14H20O2 MW:220.3074	CAS No. 101907-41-9 Carbamic acid, [4-(2-formylhydrazino)phenyl]-, phenyl ester (9CI) Catalog No.:AG0005WK MDL No.: MF:C14H13N3O3 MW:271.2713	CAS No. 101908-22-9 2-Naphthalenol, 5,6,7,8-tetrahydro-6-(4-hydroxyphenyl)-6-methyl-5-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-, (5R,6R)-rel- Catalog No.:AG0005X8 MDL No.: MF:C31H41F5O3S MW:588.7125
CAS No. 101908-41-2 Acetamide, 2-chloro-N-(2,4-dimethoxyphenyl)- Catalog No.:AG0005X7 MDL No.:MFCD00750873 MF:C10H12ClNO3 MW:229.6602	CAS No. 101908-42-3 2H-1,4-Benzoxazin-3(4H)-one, 7-methoxy-4-propyl- Catalog No.:AG0005X6 MDL No.: MF:C12H15NO3 MW:221.2524	CAS No. 101908-49-0 Propanamide, N-(2-hydroxy-4-methoxyphenyl)- Catalog No.:AG0005X5 MDL No.: MF:C10H13NO3 MW:195.2151
CAS No. 101908-73-0 1,2-Benzenediamine, N1-[1,1'-biphenyl]-2-yl- Catalog No.:AG0005X4 MDL No.: MF:C18H16N2 MW:260.3330	CAS No. 101909-42-6 1H-Indole-3-carboxylic acid, 4-chloro-, methyl ester Catalog No.:AG0005X3 MDL No.:MFCD09841616 MF:C10H8ClNO2 MW:209.6290	CAS No. 101909-43-7 1H-Indole-3-carboxylic acid, 4-bromo-, methyl ester Catalog No.:AG0005X2 MDL No.:MFCD09836009 MF:C10H8BrNO2 MW:254.0800
CAS No. 101909-44-8 1H-Indole-3-carboxylic acid, 4-iodo-, methyl ester Catalog No.:AG0005X1 MDL No.:MFCD04038681 MF:C10H8INO2 MW:301.0805	CAS No. 10191-18-1 Ethanesulfonic acid, 2-[bis(2-hydroxyethyl)amino]- Catalog No.:AG0005XH MDL No.:MFCD00007533 MF:C6H15NO5S MW:213.2520	CAS No. 10191-24-9 Hexanoic acid, 3-hydroxy- Catalog No.:AG0005XG MDL No.:MFCD02259045 MF:C6H12O3 MW:132.1577
CAS No. 10191-25-0 Pentanoic acid, 3-oxo- Catalog No.:AG0005XF MDL No.:MFCD11040434 MF:C5H8O3 MW:116.1152	CAS No. 10191-35-2 Butanoic acid, 2,3,4-trihydroxy- Catalog No.:AG0005XE MDL No.:MFCD16877117 MF:C4H8O5 MW:136.1033	CAS No. 10191-42-1 Pyridine, 2-[1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propen-1-yl]- Catalog No.:AG0005XD MDL No.: MF:C19H22N2 MW:278.3914
CAS No. 10191-61-4 Carbamodithioic acid, N-cyano-, methyl ester, potassium salt (1:1) Catalog No.:AG0005XC MDL No.:MFCD00799296 MF:C3H4KN2S2 MW:171.3056	CAS No. 10191-72-7 Cyanamide, 1,3-dithiolan-2-ylidene- (9CI) Catalog No.:AG0005XB MDL No.: MF:C4H4N2S2 MW:144.2180	CAS No. 10191-73-8 Cyanamide, 1,3-dithian-2-ylidene- (9CI) Catalog No.:AG0005XA MDL No.: MF:C5H6N2S2 MW:158.2445
CAS No. 10191-90-9 1,2,4-Thiadiazole, 3-chloro-5-(methylthio)- Catalog No.:AG0005X9 MDL No.:MFCD06658049 MF:C3H3ClN2S2 MW:166.6523	CAS No. 101910-24-1 Benzenemethanol, α-pentyl-3-(2-quinolinylmethoxy)- Catalog No.:AG0005X0 MDL No.: MF:C22H25NO2 MW:335.4394	CAS No. 101910-34-3 4-Thiazolidinecarboxylic acid, 2-(2-hydroxyphenyl)-3-[3-(methylsulfinyl)-1-oxopropyl]-, (2R,4R)- Catalog No.:AG0005WZ MDL No.: MF:C14H17NO5S2 MW:343.4185
CAS No. 101910-60-5 2H-1-Benzopyran-2-one, 3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]- Catalog No.:AG0005WY MDL No.: MF:C18H10O5 MW:306.2690	CAS No. 1019108-05-4 3H-Imidazo[4,5-b]pyridine-5-carboxylic acid Catalog No.:AG0005WX MDL No.:MFCD09863858 MF:C7H5N3O2 MW:163.1335	CAS No. 1019108-35-0 4H-Cyclopentathiazole-4-carboxylic acid, 2-amino-5,6-dihydro-, ethyl ester Catalog No.:AG0005WW MDL No.:MFCD09864118 MF:C9H12N2O2S MW:212.2688
CAS No. 1019108-45-2 Benzothiazole, 2-bromo-7-fluoro-4-methyl- Catalog No.:AG0005WV MDL No.:MFCD09749155 MF:C8H5BrFNS MW:246.0994	CAS No. 1019108-46-3 Benzothiazole, 2-bromo-4,7-difluoro- Catalog No.:AG0005XV MDL No.: MF:C7H2BrF2NS MW:250.0633	CAS No. 101911-11-9 Benzenemethanamine, N-[3-(trimethylsilyl)-2-propyn-1-ylidene]- Catalog No.:AG0005Y5 MDL No.: MF:C13H17NSi MW:215.3663
CAS No. 101911-90-4 Carbonic acid, phenyl 3-(1-piperidinyl)-1-(2-thienyl)propyl ester, hydrochloride (9CI) Catalog No.:AG0005Y4 MDL No.: MF:C19H24ClNO3S MW:381.9168	CAS No. 101911-91-5 Carbonic acid, phenyl 3-(1-pyrrolidinyl)-1-(2-thienyl)propyl ester, hydrochloride (9CI) Catalog No.:AG0005Y3 MDL No.: MF:C18H22ClNO3S MW:367.8902	CAS No. 1019111-62-6 1,3,4-Thiadiazole, 2-bromo-5-(1-methylethyl)- Catalog No.:AG0005XU MDL No.:MFCD09965539 MF:C5H7BrN2S MW:207.0915
CAS No. 1019111-64-8 Benzothiazole, 2,5-dibromo- Catalog No.:AG0005XT MDL No.:MFCD09749228 MF:C7H3Br2NS MW:292.9784	CAS No. 1019112-29-8 β-Alanine, N-[4-[(1S)-1-[(R)-(4-chlorophenyl)(7-fluoro-5-methyl-1H-indol-3-yl)methyl]butyl]benzoyl]- Catalog No.:AG0005XS MDL No.: MF:C30H30ClFN2O3 MW:521.0222	CAS No. 1019113-44-0 Benzoic acid, 4-[1-(4-chlorobenzoyl)butyl]-, 1,1-diMethylethyl ester Catalog No.:AG0005XR MDL No.: MF:C22H25ClO3 MW:372.8851
CAS No. 1019115-11-7 Benzonitrile, 3-methoxy-2-nitro-4-(phenylmethoxy)- Catalog No.:AG0005XQ MDL No.:MFCD09965535 MF:C15H12N2O4 MW:284.2668	CAS No. 1019115-53-7 2-Benzothiazolamine, 7-fluoro-4-methyl- Catalog No.:AG0005XP MDL No.: MF:C8H7FN2S MW:182.2180	CAS No. 1019115-71-9 Benzenemethanamine, 4-amino-N-ethyl- Catalog No.:AG0005XO MDL No.:MFCD09965833 MF:C9H14N2 MW:150.2209
CAS No. 1019117-09-9 Pyridine, 3-bromo-4-(1H-pyrrol-1-yl)- Catalog No.:AG0005XN MDL No.: MF:C9H7BrN2 MW:223.0693	CAS No. 1019117-36-2 Benzothiazole, 2-bromo-4,6-difluoro- Catalog No.:AG0005XM MDL No.: MF:C7H2BrF2NS MW:250.0633	CAS No. 1019117-37-3 Benzothiazole, 2-bromo-6-fluoro-4-methyl- Catalog No.:AG0005XL MDL No.:MFCD09748581 MF:C8H5BrFNS MW:246.0994
CAS No. 101912-24-7 L-Lysine, L-leucyl-L-isoleucyl-L-phenylalanyl-L-alanylglycyl- Catalog No.:AG0005Y2 MDL No.: MF:C32H53N7O7 MW:647.8059	CAS No. 1019127-04-8 4-Pyridinecarboxylic acid, 2-(propylamino)- Catalog No.:AG0005XK MDL No.:MFCD11131957 MF:C9H12N2O2 MW:180.2038	CAS No. 1019127-19-5 4-Pyridinecarboxylic acid, 2-(cyclopentylamino)- Catalog No.:AG0005XJ MDL No.:MFCD11132015 MF:C11H14N2O2 MW:206.2411
CAS No. 1019128-90-5 Benzenemethanamine, 3-(cyclohexylmethoxy)- Catalog No.:AG0005XI MDL No.:MFCD11127465 MF:C14H21NO MW:219.3226	CAS No. 101913-05-7 2H-Imidazole-2-thione, 1,3-dihydro-1-[(4-methoxy-3-nitrophenyl)methyl]- Catalog No.:AG0005Y1 MDL No.: MF:C11H11N3O3S MW:265.2883	CAS No. 101913-37-5 Benzaldehyde, 4,4'-[1,3-propanediylbis(oxy)]bis[3-methoxy- Catalog No.:AG0005Y0 MDL No.:MFCD00021063 MF:C19H20O6 MW:344.3585
CAS No. 101913-38-6 Benzaldehyde, 4,4'-[1,4-phenylenebis(methyleneoxy)]bis[3-methoxy- Catalog No.:AG0005XZ MDL No.: MF:C24H22O6 MW:406.4279	CAS No. 101913-71-7 Benzenepropanoic acid, β-methyl-β-(3-methylbutyl)- Catalog No.:AG0005XY MDL No.: MF:C15H22O2 MW:234.3340	CAS No. 101913-75-1 Heptanoic acid, 2-hydroxy-2-(1-propyn-1-yl)-, 2-methyl-1-azabicyclo[2.2.2]oct-3-yl ester Catalog No.:AG0005XX MDL No.: MF:C18H29NO3 MW:307.4278
CAS No. 101913-87-5 4-Heptanone, 1,1,1,7,7,7-hexafluoro-2,6-dihydroxy-2,6-bis(trifluoromethyl)-, 2,2-dimethylhydrazone Catalog No.:AG0005XW MDL No.: MF:C11H12F12N2O2 MW:432.2060	CAS No. 101913-93-3 4-Heptanone, 1,7-dichloro-1,1,7,7-tetrafluoro-2,6-dihydroxy-2,6-bis(trifluoromethyl)-, hydrazone Catalog No.:AG0005YL MDL No.: MF:C9H8Cl2F10N2O2 MW:437.0621	CAS No. 101914-02-7 1-Heptanamine, N,N-bis(2-chloroethyl)-, hydrochloride (1:1) Catalog No.:AG0005YK MDL No.: MF:C11H24Cl3N MW:276.6740
CAS No. 101915-49-5 Bicyclo[2.2.1]hept-2-ene-7-carboxylic acid, 5-oxo- Catalog No.:AG0005YJ MDL No.: MF:C8H8O3 MW:152.1473	CAS No. 101916-65-8 Propane, 1,2-dibromo-, (2S)- (9CI) Catalog No.:AG0005YI MDL No.: MF:C3H6Br2 MW:201.8877	CAS No. 101916-69-2 Propane, 1,2-dibromo-, (2R)- (9CI) Catalog No.:AG0005YH MDL No.: MF:C3H6Br2 MW:201.8877
CAS No. 101916-99-8 2(3H)-Furanone, 5-(3-buten-1-ylidene)dihydro-, (5E)- Catalog No.:AG0005YG MDL No.: MF:C8H10O2 MW:138.1638	CAS No. 101917-77-5 [1,2,5]Oxadiazolo[3,4-g]quinoxaline (9CI) Catalog No.:AG0005YF MDL No.: MF:C8H4N4O MW:172.1436	CAS No. 10192-32-2 1-Tetracosene Catalog No.:AG0005YR MDL No.: MF:C24H48 MW:336.6379
CAS No. 10192-46-8 Boric acid (H3BO3), zinc salt (2:3) Catalog No.:AG0005YQ MDL No.: MF: MW:	CAS No. 10192-61-7 Thallium, bromodiphenyl- Catalog No.:AG0005YP MDL No.: MF:C12H10BrTl MW:438.4951	CAS No. 10192-62-8 Phenol, 4,4'-(1-methylethylidene)bis-, 1,1'-diacetate Catalog No.:AG0005YO MDL No.:MFCD00026194 MF:C19H20O4 MW:312.3597
CAS No. 10192-85-5 2-Propenoic acid, potassium salt (1:1) Catalog No.:AG0005YN MDL No.:MFCD00067206 MF:C3H3KO2 MW:110.1530	CAS No. 10192-87-7 Benzoic acid, 5-(chloromethyl)-2-hydroxy- Catalog No.:AG0005YM MDL No.:MFCD06662321 MF:C8H7ClO3 MW:186.5924	CAS No. 1019208-03-7 2H-1,5,3-Dioxazepine, tetrahydro-3-(phenylmethyl)- Catalog No.:AG0005Y7 MDL No.: MF:C11H15NO2 MW:193.2423
CAS No. 1019208-04-8 Spiro[3-azabicyclo[3.2.1]octane-8,2'-[1,3]dioxolane], 3-(phenylmethyl)- Catalog No.:AG0005Y6 MDL No.: MF:C16H21NO2 MW:259.3434	CAS No. 101923-26-6 Manganocene, 1,1'-diethyl- Catalog No.:AG0005YE MDL No.: MF:C14H18Mn MW:241.2308	CAS No. 101925-22-8 3-Pyridinol, 4-butyl- Catalog No.:AG0005YD MDL No.: MF:C9H13NO MW:151.2056
CAS No. 101925-26-2 3-Pyridinol, 4-phenyl- Catalog No.:AG0005YC MDL No.:MFCD04114251 MF:C11H9NO MW:171.1953	CAS No. 101925-47-7 Pentanamide, 2-amino-, hydrochloride (1:1), (2S)- Catalog No.:AG0005YB MDL No.:MFCD00237404 MF:C5H13ClN2O MW:152.6225	CAS No. 101925-74-0 9,12,15-Octadecatrienoic acid, 3-hydroxypropyl ester, (Z,Z,Z)- (9CI) Catalog No.:AG0005YA MDL No.: MF:C21H36O3 MW:336.5087
CAS No. 101926-93-6 Carbamic acid, (3-hydroxy-2,2-dimethyl-4-pentenyl)-, methyl ester (9CI) Catalog No.:AG0005Y9 MDL No.: MF:C9H17NO3 MW:187.2362	CAS No. 101927-24-6 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, docosyl ester, (2E)- Catalog No.:AG0005Y8 MDL No.: MF:C32H54O4 MW:502.7688	CAS No. 101927-31-5 2-Propenoic acid, 2-methyl-, 3-(4-formylphenoxy)-2-hydroxypropyl ester Catalog No.:AG0005ZB MDL No.: MF:C14H16O5 MW:264.2738
CAS No. 101927-50-8 Benzamide, 4-(1,1-dimethylethyl)-N-propyl- Catalog No.:AG0005ZA MDL No.: MF:C14H21NO MW:219.3226	CAS No. 101927-97-3 Butanamide, 2-[2-(4-methylphenyl)hydrazinylidene]-3-oxo-N-2-pyridinyl- Catalog No.:AG0005Z9 MDL No.: MF:C16H16N4O2 MW:296.3238	CAS No. 101929-87-7 Pentanoic acid, 3-oxo-4-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]-, methyl ester Catalog No.:AG0005Z8 MDL No.: MF:C18H16F3NO5 MW:383.3185
CAS No. 10193-13-2 Acetamide, N-ethenyl-N-propyl- Catalog No.:AG0005ZF MDL No.: MF:C7H13NO MW:127.1842	CAS No. 10193-26-7 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-8-(2-propen-1-yl)- Catalog No.:AG0005ZE MDL No.: MF:C12H12O3 MW:204.2219	CAS No. 10193-30-3 Sulfuric acid, monohydrate (8CI,9CI) Catalog No.:AG0005ZD MDL No.: MF:H4O5S MW:116.0938
CAS No. 10193-95-0 Acetic acid, 2-mercapto-, 1,1'-(1,4-butanediyl) ester Catalog No.:AG0005ZC MDL No.:MFCD00266655 MF:C8H14O4S2 MW:238.3244	CAS No. 101930-01-2 Butanoic acid, 3-oxo-, (3S)-1-(phenylmethyl)-3-pyrrolidinyl ester Catalog No.:AG0005Z7 MDL No.: MF:C15H19NO3 MW:261.3163	CAS No. 101930-07-8 3-Pyrrolidinol, 1-(phenylmethyl)-, (3R)- Catalog No.:AG0005Z6 MDL No.:MFCD00075484 MF:C11H15NO MW:177.2429
CAS No. 101930-95-4 Propanedioic acid, 1,3-bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl] ester Catalog No.:AG0005Z5 MDL No.: MF:C15H24O8 MW:332.3463	CAS No. 101931-17-3 2-Naphthaleneacetamide, N-(2-aminophenyl)-N-[2-(diethylamino)ethyl]- Catalog No.:AG0005Z4 MDL No.: MF:C24H29N3O MW:375.5066	CAS No. 101931-20-8 1,5-Naphthalenedisulfonic acid, 3-[2-[4-[bis(2-chloroethyl)amino]phenyl]diazenyl]- Catalog No.:AG0005Z3 MDL No.: MF:C20H19Cl2N3O6S2 MW:532.4174
CAS No. 101931-23-1 2-Naphthalenemethanol, 2-(hydrogen sulfate), sodium salt (1:1) Catalog No.:AG0005Z2 MDL No.: MF:C11H10NaO4S MW:261.2495	CAS No. 101931-27-5 2-Oxazolamine, N-[(4-ethoxy-1-naphthalenyl)methyl]-4,5-dihydro- Catalog No.:AG0005Z1 MDL No.: MF:C16H18N2O2 MW:270.3263	CAS No. 101931-30-0 1-Naphthalenemethanamine, 4-(1-methylethoxy)-, hydrobromide (1:1) Catalog No.:AG0005Z0 MDL No.: MF:C14H18BrNO MW:296.2028
CAS No. 101931-31-1 1-Naphthalenemethanamine, 4-methoxy- Catalog No.:AG0005YZ MDL No.:MFCD06213084 MF:C12H13NO MW:187.2377	CAS No. 101931-37-7 2-Oxazolamine, 4,5-dihydro-N-[(5,6,7,8-tetrahydro-1-naphthalenyl)methyl]- Catalog No.:AG0005YY MDL No.: MF:C14H18N2O MW:230.3055	CAS No. 101931-38-8 2-Naphthalenesulfonic acid, 6-[2-[4-[bis(2-chloroethyl)amino]phenyl]diazenyl]- Catalog No.:AG0005YX MDL No.: MF:C20H19Cl2N3O3S MW:452.3542
CAS No. 101931-57-1 2,4-Pentanediol, 1,1,1-trifluoro-4-methyl-2-(trifluoromethyl)- Catalog No.:AG0005YW MDL No.: MF:C7H10F6O2 MW:240.1435	CAS No. 101931-59-3 2,4-Pentanediol, 1,1,1-trifluoro-4-(4-methylphenyl)-2-(trifluoromethyl)- Catalog No.:AG0005YV MDL No.: MF:C13H14F6O2 MW:316.2395	CAS No. 101931-60-6 1,2-Pentanedione, 5,5,5-trifluoro-4-hydroxy-1-(4-nitrophenyl)-4-(trifluoromethyl)- Catalog No.:AG0005YU MDL No.: MF:C12H7F6NO5 MW:359.1781
CAS No. 101931-81-1 Hydrazinecarboxamide, 2-[3,5,5-trimethyl-6-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2-cyclohexen-1-ylidene]- Catalog No.:AG0005ZY MDL No.: MF:C13H17F6N3O2 MW:361.2834	CAS No. 101931-82-2 Hydrazinecarbothioamide, 2-[3,5,5-trimethyl-6-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2-cyclohexen-1-ylidene]- Catalog No.:AG0005ZX MDL No.: MF:C13H17F6N3OS MW:377.3490	CAS No. 101931-96-8 Benzeneacetic acid, α-(1-hydroxycyclopentyl)-, 1-azabicyclo[2.2.2]oct-3-yl ester Catalog No.:AG0005ZW MDL No.: MF:C20H27NO3 MW:329.4333
CAS No. 101932-00-7 Cyclopentanecarboxamide, N,N-dimethyl-1-phenyl- Catalog No.:AG0005ZV MDL No.: MF:C14H19NO MW:217.3068	CAS No. 101932-01-8 Cyclopentanecarboxamide, N-methyl-1-phenyl- Catalog No.:AG0005ZU MDL No.: MF:C13H17NO MW:203.2802	CAS No. 101932-09-6 Cyclopentaneacetic acid, α-hydroxy-α-1-propen-1-yl-, 1-azabicyclo[2.2.2]oct-3-yl ester Catalog No.:AG0005ZT MDL No.: MF:C17H27NO3 MW:293.4012
CAS No. 101932-10-9 Cyclopentaneacetic acid, α-hydroxy-α-1-propyn-1-yl-, 1-(2-propen-1-yl)-4-piperidinyl ester Catalog No.:AG0005ZS MDL No.: MF:C18H27NO3 MW:305.4119	CAS No. 101932-16-5 Cyclopentanone, 2,5-bis[2-chloro-1-(chlorodifluoromethyl)-2,2-difluoro-1-hydroxyethyl]- Catalog No.:AG0005ZR MDL No.: MF:C11H8Cl4F8O3 MW:481.9786	CAS No. 101932-18-7 Cyclopentanone, 2,5-bis[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]- Catalog No.:AG0005ZQ MDL No.: MF:C11H8F12O3 MW:416.1603
CAS No. 101932-22-3 Hydrazinecarbothioamide, 2-[2-[2-chloro-1-(chlorodifluoromethyl)-2,2-difluoro-1-hydroxyethyl]cyclopentylidene]- Catalog No.:AG0005ZP MDL No.: MF:C9H11Cl2F4N3OS MW:356.1678	CAS No. 101932-27-8 2-Oxazolidinone, 5-[2-methoxy-4-(2-propen-1-yl)phenoxy]- Catalog No.:AG0005ZO MDL No.: MF:C13H15NO4 MW:249.2625	CAS No. 101932-29-0 2-Oxazolidinone, 5-(2-methoxy-4-propylphenoxy)- Catalog No.:AG0005ZN MDL No.: MF:C13H17NO4 MW:251.2784
CAS No. 101932-31-4 2-Oxazolamine, N-cyclododecyl-4,5-dihydro- Catalog No.:AG0005ZM MDL No.: MF:C15H28N2O MW:252.3956	CAS No. 101932-42-7 Oxazole, 4,5-dihydro-2-[4-(2-phenyldiazenyl)phenyl]- Catalog No.:AG0005ZL MDL No.: MF:C15H13N3O MW:251.2832	CAS No. 101932-46-1 Oxazole, 4,5-dihydro-2-(3,4,5-trimethoxyphenyl)- Catalog No.:AG0005ZK MDL No.: MF:C12H15NO4 MW:237.2518
CAS No. 101932-75-6 Manganocene, 1,1',2,2',3,3',4,4'-octamethyl- (9CI) Catalog No.:AG0005ZJ MDL No.: MF: MW:	CAS No. 101932-91-6 Anthracene, 9-[(1E)-2-(1-naphthalenyl)ethenyl]- Catalog No.:AG0005ZI MDL No.: MF:C26H18 MW:330.4211	CAS No. 1019324-25-4 4-Pyridinecarboxylic acid, 2-[(2-methylphenyl)amino]- Catalog No.:AG0005ZG MDL No.:MFCD11132204 MF:C13H12N2O2 MW:228.2466