Thiols/Mercaptans

Organosulfur Compounds

Both thiols and mercaptans are organosulfur compounds that contain a sulfur-hydrogen bond, analogous to the hydroxyl group (-OH) of alcohol. The chemical differences between oxygen and sulfur give the group its unique properties. Not only is the -SH group an acid, but it is also a nucleophile for attacks on saturated carbon. In vivo, the amino acid cysteine, whose functional group is a thiol, is essential for protein structure because of its ability to create a disulfide bond with a second cysteine, and is often involved in the active site of the enzyme.

Sigma-Aldrich offers a wide range of thiols and mercaptans. These compounds can be used as building blocks for organic syntheses and are useful in syntheses including redox chemistry, alkylations, Michael additions, and cross-coupling reactions. Commonly used reagents for the reduction of protein disulfide bonds and retardation of oxidation of biological compounds in solution, such as 2-mercaptoethanol, are available in addition to alkyl and aryl thiols/mercaptans and their halogenated derivatives.

Compounds with multiple thiol/mercaptan functional groups make it possible to prepare derivatives with multiple functionalities, such as Boc-protected amine functional groups. Biomolecules derivatized with thiols, such as glycosyl disulfides, have shown interesting biological activities, including anticancer properties. Thiols can even be used as chiral auxiliaries as a means of synthesizing enantiomerically enriched compounds (for example, the synthesis of lactam stereocenters).

Product #

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Description

Molecular Formula

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332895 Trichloromethanesulfenyl chloride ≥96% CCl4S
374008 2,2,2-Trifluoroethanethiol 95% C2H3F3S
CDS012623 5-mercapto-4H-[1,2,4]triazol-3-ol AldrichCPR C2H3N3OS
528056 Thioglycolic acid ≥99% C2H4O2S
M6250 2-Mercaptoethanol ≥99.0% C2H6OS
E3708 Ethanethiol 97% C2H6S
02390 1,2-Ethanedithiol ≥98.0% (GC) C2H6S2
398020 1,2-Ethanedithiol technical grade, ≥90% C2H6S2
CDS014592 methyl aminomethanimidothioate hydroiodide AldrichCPR C2H7IN2S
10010 Ammonium thioglycolate solution ~60% in H2O C2H7NO2S
M9768 Cysteamine ~95% C2H7NS
108995 Methyl thioglycolate 95% C3H6O2S
T31003 Thiolactic acid 95% C3H6O2S
06030 2-Propene-1-thiol technical, ~60% (GC) C3H6S
C68601 3-Chloro-1-propanethiol 98% C3H7ClS
778672 L-Cysteine produced by Wacker Chemie AG, Burghausen, Germany, ≥98.0% C3H7NO2S
328375 1-Mercapto-2-propanol 95% C3H8OS
CDS011871 2-methoxyethanethiol AldrichCPR C3H8OS
405736 3-Mercapto-1-propanol 95% C3H8OS
D1129 2,3-Dimercapto-1-propanol C3H8OS2
64046 2,3-Dimercapto-1-propanol ≥98% (iodometric) C3H8OS2
88642 1-Thioglycerol dist., ≥98.0% (GC) C3H8O2S
59590 2-Propanethiol ≥97.0% (GC) C3H8S
P50773 2-Propanethiol ≥97% C3H8S
P50609 1,3-Propanedithiol 99% C3H8S2
88460 Mercaptosuccinic acid ReagentPlus®, ≥99.0% (HPLC) C4H6O4S
M6182 Mercaptosuccinic acid 97% C4H6O4S
D7881 meso-2,3-Dimercaptosuccinic acid ~98% C4H6O4S2
CDS012290 4-ethyl-5-mercapto-4H-1,2,4-triazol-3-ol AldrichCPR C4H7N3OS
CDS013450 4-ethyl-4H-1,2,4-triazole-3-thiol AldrichCPR C4H7N3S
CDS017489 5-ethyl-4H-1,2,4-triazole-3-thiol AldrichCPR C4H7N3S
CDS006442 N-Carbamoyl-L-cysteine AldrichCPR C4H8N2O3S
CDS006923 2-mercaptoisobutyric acid AldrichCPR C4H8O2S
CDS000283 2-Methyl-3-sulfanylpropanoic acid AldrichCPR C4H8O2S
CDS004545 4-mercaptobutyric acid AldrichCPR C4H8O2S
363340 N-Acetylcysteamine 95% C4H9NOS
451878 4-Mercapto-1-butanol 95% C4H10OS
M3809 2-Mercaptoethyl ether 95% C4H10OS2
112925 1-Butanethiol 99% C4H10S
112917 2-Methyl-1-propanethiol 92%, technical grade C4H10S
109207 2-Methyl-2-propanethiol 99% C4H10S
B85404 1,4-Butanedithiol 97% C4H10S2
M4007 2,2′-Thiodiethanethiol technical grade, 90% C4H10S3
CDS000504 Ethanolamine thioglycolate (~85% in water) AldrichCPR C4H11NO3S
CDS010827 4-Cyclopropyl-4H-1,2,4-triazole-3-thiol AldrichCPR C5H7N3S
CDS012038 5-Cyclopropyl-4H-1,2,4-triazole-3-thiol AldrichCPR C5H7N3S
692581 4-Cyano-1-butanethiol 97% C5H9NS
CDS012280 4-(2-methoxyethyl)-4H-1,2,4-triazole-3-thiol AldrichCPR C5H9N3OS
CDS000220 3-Sulfanyl-2-pentanone AldrichCPR C5H10OS
319708 Cyclopentanethiol 97% C5H10S
632295 2-(2-Methoxyethoxy)ethanethiol 97% C5H12O2S
191132 2-Methyl-1-butanethiol 95% C5H12S
115924 3-Methyl-1-butanethiol 97% C5H12S
242551 1,5-Pentanedithiol 96% C5H12S2
364681 2-(Trimethylsilyl)ethanethiol 95% C5H14SSi
P5654 2,3,4,5,6-Pentafluorothiophenol 97% C6HF5S
100188 2,3,5,6-Tetrafluorobenzenethiol 97% C6H2F4S
662526 2,3-Dichlorothiophenol 97% C6H4Cl2S
540862 2,4-Dichlorobenzenethiol 97% C6H4Cl2S
144274 2,5-Dichlorobenzenethiol 98% C6H4Cl2S
144266 3,4-Dichlorobenzenethiol 97% C6H4Cl2S
540870 3,5-Dichlorobenzenethiol 97% C6H4Cl2S
537233 2,4-Difluorothiophenol 97% C6H4F2S
549223 3,4-Difluorothiophenol 96% C6H4F2S
242659 2-Bromothiophenol 97% C6H5BrS
259306 3-Bromothiophenol 95% C6H5BrS
B81956 4-Bromothiophenol 95% C6H5BrS
247146 2-Chlorothiophenol 99% C6H5ClS
242675 3-Chlorobenzenethiol 97% C6H5ClS
125237 4-Chlorothiophenol 97% C6H5ClS
275379 2-Fluorothiophenol 97% C6H5FS
275387 3-Fluorothiophenol 95% C6H5FS
F15315 4-Fluorothiophenol 98% C6H5FS
N27209 4-Nitrothiophenol technical grade, 80% C6H5NO2S
JRD0216 2-Mercapto-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one AldrichCPR C6H5N3OS
CDS011798 4-Aminothieno[2,3-d]pyrimidine-2-thiol AldrichCPR C6H5N3S2
541850 2-Amino-4-chlorobenzenethiol 96% C6H6ClNS
CDS012030 1-Methyl-1H-pyrazolo[3,4-d]pyrimidine-4-thiol AldrichCPR C6H6N4S
465348 2-Mercaptophenol 95% C6H6OS
568899   3-Mercaptophenol 96% C6H6OS
559938 4-Mercaptophenol 97% C6H6OS
275395 4-Mercaptophenol technical grade, 90% C6H6OS
89021 Thiophenol purum, ≥98.0% (GC) C6H6S
240249 Thiophenol ≥99% C6H6S
T32808 Thiophenol 97% C6H6S
269093 1,3-Benzenedithiol 99% C6H6S2
270865 Benzene-1,2-dithiol 96% C6H6S2
274240 2-Aminothiophenol 99% C6H7NS
123137 2-Aminothiophenol technical grade, 90% C6H7NS
143480 3-Aminothiophenol 96% C6H7NS
422967 4-Aminothiophenol 97% C6H7NS
JRD0261 4-Amino-2-(methylmercapto)-7H-pyrazole[2,3-d]pyrimidine AldrichCPR C6H7N5S
CDS012295 4-(3-methoxypropyl)-4H-1,2,4-triazole-3-thiol AldrichCPR C6H11N3OS
CDS009189 4-methyl-4-mercaptopentan-2-one AldrichCPR C6H12OS
CDS012047 3-Mercapto-3-methyl-1-butyl-1-formate AldrichCPR C6H12O2S
CDS010775 3-mercaptobutyl acetate AldrichCPR C6H12O2S
674974 6-Mercaptohexanoic acid 90% C6H12O2S
C105600 Cyclohexanethiol 97% C6H12S
CDS001520 3-Mercapto-1-hexanol AldrichCPR C6H14OS
CDS012171 4-mercapto-4-methylpentan-2-ol AldrichCPR C6H14OS
725226 6-Mercapto-1-hexanol 99% C6H14OS
725382 1,6-Hexanedithiol 99.5% C6H14S2
B89507 2-(Butylamino)ethanethiol 97% C6H15NS
ANV00148 7-Fluorobenzo[d]thiazole-2-thiol AldrichCPR C7H4FNS2
528196 5-Fluoro-2-mercaptobenzoic acid 96% C7H5FO2S
CDS000809 2-(Trifluoromethoxy)thiophenol AldrichCPR C7H5F3OS
CDS000823 3-(Trifluoromethoxy)thiophenol AldrichCPR C7H5F3OS
542660 2-(Trifluoromethyl)benzenethiol 96% C7H5F3S
CDS007777 4-bromo-2-fluorobenzyl mercaptan AldrichCPR C7H6BrFS
CDS003831 4-chloro-2-fluorobenzyl mercaptan AldrichCPR C7H6ClFS
CDS006153 2,6-difluorobenzyl mercaptan AldrichCPR C7H6F2S
CDS003759 3,4-difluorobenzyl mercaptan AldrichCPR C7H6F2S
CDS003557 3,5-difluorobenzyl mercaptan AldrichCPR C7H6F2S
365734 2-Amino-4-(trifluoromethyl)benzenethiol hydrochloride 97% C7H6F3NS · HCl
451436 3-Mercaptobenzoic acid 95% C7H6O2S
662534 4-Mercaptobenzoic acid technical grade, 90% C7H6O2S
706329 4-Mercaptobenzoic acid 99% C7H6O2S
T33200 Thiosalicylic acid 97% C7H6O2S
593982 2-Bromobenzyl mercaptan 97% C7H7BrS
CDS003563 3-bromobenzylmercaptan AldrichCPR C7H7BrS
566950 4-Bromobenzyl mercaptan 97% C7H7BrS
257427 2-Chlorobenzenemethanethiol 98% C7H7ClS
C28707 4-Chlorobenzenemethanethiol 98% C7H7ClS
639249 5-Fluoro-2-mercaptobenzyl alcohol 97% C7H7FOS
539155 4-Fluorobenzyl mercaptan 96% C7H7FS
566942 (3-Nitrobenzyl)mercaptan 97% C7H7NO2S
755346 (4-Nitrobenzyl)mercaptan 95% C7H7NO2S
439525 2-Mercaptobenzyl alcohol technical grade C7H8OS
184055 2-Methoxythiophenol 97% C7H8OS
155705 3-Methoxythiophenol 98% C7H8OS
550426 4-(Methylmercapto)phenol 98% C7H8OS
65357 4-Methoxythiophenol purum, ≥98.0% (GC) C7H8OS
109525 4-Methoxythiophenol 97% C7H8OS
T28509 2-Methylbenzenethiol 95% C7H8S
T28517 3-Methylbenzenethiol 95% C7H8S
13540 Benzyl mercaptan purum, ≥99.0% (GC) C7H8S
B25401 Benzyl mercaptan 99% C7H8S
662496 4-(Methylsulfanyl)thiophenol 96% C7H8S2
D129208 Toluene-3,4-dithiol technical grade, 90% C7H8S2
CDS012300 (3-mercapto-5-propyl-4H-1,2,4-triazol-4-yl)acetic acid AldrichCPR C7H11N3O2S
CDS011862 Ethyl (5-mercapto-4-methyl-4H-1,2,4-triazol-3-yl)acetate AldrichCPR C7H11N3O2S
458910 2-(Boc-amino)ethanethiol 97% C7H15NO2S
536083 3,5-Bis(trifluoromethyl)benzenethiol 97% C8H4F6S
CDS000249   4-(5-Sulfanyl-1H-tetraazol-1-yl)benzoic acid AldrichCPR C8H6N4O2S
CDS003636 4-(trifluoromethoxy)benzyl mercaptan AldrichCPR C8H7F3OS
CDS003799 4-trifluoromethylbenzyl mercaptan AldrichCPR C8H7F3S
CDS016588 2-(5-sulfanyl-4H-1,2,4-triazol-3-yl)phenol AldrichCPR C8H7N3OS
CDS011365 4-(mercaptomethyl)benzoic acid AldrichCPR C8H8O2S
653152 4-Mercaptophenylacetic acid 97% C8H8O2S
357758 Methyl thiosalicylate 97% C8H8O2S
A8201 4-Acetamidothiophenol ≥90% C8H9NOS
549231 3-Ethoxythiophenol 97% C8H10OS
113158 4-Methoxy-α-toluenethiol 90%, technical grade C8H10OS
275425 2,5-Dimethoxythiophenol 98% C8H10O2S
662518 3,4-Dimethoxythiophenol 97% C8H10O2S
CDS000677 1-Phenylethyl mercaptan AldrichCPR C8H10S
275441 2,4-Dimethylbenzenethiol 95% C8H10S
275468 2,5-Dimethylbenzenethiol 97% C8H10S
306940 2,6-Dimethylbenzenethiol 95% C8H10S
307998 2-Ethylbenzenethiol technical grade, 90% C8H10S
252581 2-Phenylethanethiol 98% C8H10S
269689 3,4-Dimethylbenzenethiol 98% C8H10S
522929 3,5-Dimethylbenzenethiol 90% C8H10S
306738 1,2-Benzenedimethanethiol 95% C8H10S2
306983 1,3-Benzenedimethanethiol 95% C8H10S2
147273 1,4-Benzenedimethanethiol 98% C8H10S2
CDS006116 4-(dimethylamino)thiophenol AldrichCPR C8H11NS
CDS010304 Boc-D-Cys-OH AldrichCPR C8H15NO4S
675075 8-Mercaptooctanoic acid 95% C8H16O2S
706922 8-Mercapto-1-octanol 98% C8H18OS
669148 2-Ethylhexanethiol 97% C8H18S
CDS007720 5-(3-Methoxy-phenyl)-4H-[1,2,4]triazole-3-thiol AldrichCPR C9H9N3OS
CDS011027 4-Amino-5-(benzylthio)-4H-1,2,4-triazole-3-thiol AldrichCPR C9H10N4S2
CDS013927 mercapto glycolic benzoic acid AldrichCPR C9H10O4S
I27503 2-Isopropylbenzenethiol technical grade, 90% C9H12S
540854 4-Isopropylbenzenethiol 95% C9H12S
698768 9-Mercapto-1-nonanol 96% C9H20OS
674273 1-Nonanethiol 99% C9H20S
724742 1-Naphthalenethiol 99% C10H8S
270849 2-Naphthalenethiol 99% C10H8S
CDS017521 (5-mercapto-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl-methanol AldrichCPR C10H11N3OS
CDS018523 5-(2-ethoxy-phenyl)-4H-[1,2,4]triazole-3-thiol AldrichCPR C10H11N3OS
CDS014122 2-(1,4,5,6-tetrahydro-2-pyrimidinyl)benzenethiol AldrichCPR C10H12N2S
428450 2,4,6-Trimethylbenzyl mercaptan 98% C10H14S
593656 4-tert-Butylbenzenethiol 97% C10H14S
719234 1-Adamantanethiol 99% (GC) C10H16S
88670 2-Ethylhexyl thioglycolate ≥95.0% (GC) C10H20O2S
30640 1-Decanethiol technical, ≥95% (GC) C10H22S
705233 1-Decanethiol 99% C10H22S
738344 Naphthalene-1-thiocarboxamide 97% C11H9NS
CDS018820 5-cyclopropyl-4-phenyl-4H-[1,2,4]triazole-3-thiol AldrichCPR C11H11N3S
548715 4-tert-Butylbenzyl mercaptan C11H16S
674427 11-Mercaptoundecanoic acid 98% C11H22O2S
701335 11-Bromo-1-undecanethiol 99% C11H23BrS
CDS006870 5-Phenylthieno[2,3-d]pyrimidine-4(3H)-thione AldrichCPR C12H8N2S2
673099 Biphenyl-4,4′-dithiol 95% C12H10S2
381497 Trimethylolpropane tris(2-mercaptoacetate) technical grade C12H20O6S3
675067 12-Mercaptododecanoic acid 96% C12H24O2S
CDS012049 3-mercaptohexyl hexanoate AldrichCPR C12H24O2S
686492 3-Mercapto-N-nonylpropionamide 95% C12H25NOS
44130 1-Dodecanethiol purum, ≥97.0% (GC) C12H26S
701696 4,4′-Dimercaptostilbene >96% C14H12S2
716049 4,4′-Bis(mercaptomethyl)biphenyl 97% C14H14S2
381489 Trimethylolpropane tris(3-mercaptopropionate) ≥95.0% C15H26O6S3
682527 6-(Ferrocenyl)hexanethiol C16H22FeS
674435 16-Mercaptohexadecanoic acid 99% C16H32O2S
674516 1-Hexadecanethiol 99% C16H34S
52270 1-Hexadecanethiol ≥95.0% (GC) C16H34S
674400 1,16-Hexadecanedithiol 99% C16H34S2
728640 11-Mercaptoundecylhydroquinone 95% C17H28O2S
CDS000401 Ponceau SX AldrichCPR C18H14N2Na2O7S2
704709 p-Terphenyl-4,4′′-dithiol 95% C18H14S2
719692 cis-9-Octadecene-1-thiol 97% C18H36S
74731 1-Octadecanethiol purum, ≥95.0% (GC) C18H38S
T84107 Triphenylmethanethiol 97% C19H16S
CDS018559 h-cys(trt)-nh2 AldrichCPR C22H22N2OS