CAS 2365-48-2 Methyl thioglycolate - Catalysts / Alfa Chemistry

Synonyms

RP18865; methyl-2-mercaptoacetate; Methyl sulfanylacetate #; mercapto-acetic acid methylester; NSC-75117; 2365-48-2; MCULE-3020830180; Acetic acid, 2-mercapto-, methyl ester; TRA0039347; Thioglykolsaeure-methylester;

IUPAC Name

methyl 2-sulfanylacetate;

Molecular Weight

106.139g/mol

Molecular Formula

C3H6O2S;

Canonical SMILES

COC(=O)CS;

InChI

InChI=1S/C3H6O2S/c1-5-3(4)2-6/h6H,2H2,1H3;

InChI Key

MKIJJIMOAABWGF-UHFFFAOYSA-N;

Storage

Store below +30°C.

Complexity

52.8

Covalently-Bonded Unit Count

Decomposition

When heated to decomposition it emits toxic fumes of sulfoxides.;

EC Number

219-121-7

Exact Mass

106.009g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

106.009g/mol

NSC Number

75117

Rotatable Bond Count

Topological Polar Surface Area

27.3A^2

Undefined Atom Stereocenter Count

UNII

O1608LA9EL

Vapor Pressure

3.00 mmHg;

Application

Methyl thioglycolate is a clear, colorless liquid derived from thioglycolic acid, an organic compound with both thiol and carboxylic acid functional groups. It plays a significant role in organic synthesis, commonly used as a nucleophile in thioglycolysis reactions and as a sulfur transfer agent in sulfonyl chloride synthesis. Additionally, methyl thioglycolate has been investigated for its effects on neocarzinostatin activation and DNA damage expression. This versatile compound is employed in the preparation of various chemical entities, such as 3-carbomethoxy-4-oxotetrahydrothiopyran and carbomethoxy-oxotetrahydrothiophenes, and is integral in the synthesis of methyl thioglycolate and aminoethanethiol conjugated gold nanorods. Its reactivity includes forming adducts with the nonprotein component of the antitumor antibiotic neocarzinostatin and reacting with isothiocyanates to produce rhodanine. In the pharmaceutical industry, methyl thioglycolate is utilized as an intermediate in manufacturing anti-inflammatory drugs like aspirin and ibuprofen and in developing treatments for autoimmune diseases. Furthermore, it can bind to amino acids on bacterial surfaces, impairing their function and leading to cell death, highlighting its utility in therapeutic applications.

January 8, 2025

Essential for Innovative Chemical Synthesis

Methyl thioglycolate from Alfa Chemistry, a clear, colorless liquid, was crucial in synthesizing anti-inflammatory drugs in our lab. Its reliable performance in reactions made it indispensable for our research. Highly recommended for pharmaceutical applications!