Methyl thioglycolate

Base Information

• Chemical Name: Methyl thioglycolate
• CAS No.: 2365-48-2
• Deprecated CAS: 64807-90-5,1629585-98-3
• Molecular Formula: C3H6 O2 S
• Molecular Weight: 106.145
• Hs Code.: 29309070
• European Community (EC) Number: 219-121-7
• NSC Number: 75117
• UNII: O1608LA9EL
• DSSTox Substance ID: DTXSID0033673
• Nikkaji Number: J54.943F
• Wikidata: Q27285190
• ChEMBL ID: CHEMBL1341329
• Mol file: 2365-48-2.mol

Synonyms:methyl mercaptoacetate;methyl thioglycolate;methyl thioglycolate, sodium salt;thioglycolic acid methyl ester

Chemical Property of Methyl thioglycolate

Chemical Property:

• Appearance/Colour: colorless or palegreen liquid
• Vapor Pressure: 3.58mmHg at 25°C
• Melting Point: -24 ºC
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 42-43 ºC (10 mmHg)
• PKA: 8.04±0.10(Predicted)
• Flash Point: 56 ºC
• PSA: 65.10000
• Density: 1.187
• LogP: 0.08920
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 40g/l
• Water Solubility.: 40 g/L (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 106.00885060
• Heavy Atom Count: 6
• Complexity: 52.8

Purity/Quality:

98% ^*data from raw suppliers

Methyl thioglycolate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 10-20/22-36/37/38-25
• Safety Statements: 26-36/37-45-36/37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thioglycolates
• Canonical SMILES: COC(=O)CS
• Uses: Methyl Thioglycolate is an derivative of Thioglycolic Acid (T350760), an organic compound containing both a thiol and a carboxylic acid functional groups. Thioglycolic Acid and its derivatives are oft en used in organic synthesis as a nucleophile in thioglycolysis reactions and is also used as a S transfer agent for sulfonyl chloride synthesis. Methyl Thioglycolate have been studied for the its inf luence on neocarzinostatin activation and expression of DNA damage. Methyl thioglycolate was used in the preparation of 3-carbomethoxy-4- oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene. It is used to prepare methyl thioglycolate and aminoethanethiol conjugated gold nanorods.

Technology Process of Methyl thioglycolate

There total 13 articles about Methyl thioglycolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

methanol (67-56-1) + mercaptoacetic acid (68-11-1) → Methyl thioglycolate (2365-48-2)

Guidance literature:

With sulfuric acid; for 4h; Reflux;

DOI:10.1002/anie.202016228

Reference yield: 85.0%

methyl bis(thioacetate) (1665-64-1) → Methyl thioglycolate (2365-48-2)

Guidance literature:

With magnesium; In methanol; for 2h; Ambient temperature;

DOI:10.1080/00397919708006063

Reference yield: 3.0%

(N-Phenyl-formimidoylsulfanyl)-acetic acid methyl ester (84495-75-0) → mercaptoacetic acid (68-11-1) + Methyl thioglycolate (2365-48-2)

Guidance literature:

With hydrogenchloride; In water; Ambient temperature;

upstream raw materials:

methanol

mercaptoacetic acid

3-methyl-thiazolidine-2,4-dione

C₁₈H₁₈NO₅S^(1-)

Downstream raw materials:

dimethyl-3-thiaadipate

methoxycarbonylmethylsulfanyl-fumaric acid dimethyl ester

2,2-bis-methoxycarbonylmethylsulfanyl-succinic acid dimethyl ester

dimethyl 3-hydroxythiophene-2,5-dicarboxylate

Refernces

• 1、 Wang, Yanchao,Li, Maosheng,Wang, Shixue,Tao, Youhua,Wang, Xianhong. "S-Carboxyanhydrides: Ultrafast and Selective Ring-Opening Polymerizations Towards Well-defined Functionalized Polythioesters". . p. 10798 - 10805. Retrieved 2021.
• 2、 Hadley, Erik B.,Gellman, Samuel H.. "An antiparallel α-helical coiled-coil model system for rapid assessment of side-chain recognition at the hydrophobic interface". . p. 16444 - 16445. Retrieved 2006.
• 3、 Tan, Chunbin,Liu, Xiaoling,Du, Hongfei. "The novel method to synthesis of cantharidin intermediate". . p. 271 - 276. Retrieved 2019/07/31.