S-(Thiobenzoyl)thioglycolic acid

Base Information

• Chemical Name: S-(Thiobenzoyl)thioglycolic acid
• CAS No.: 942-91-6
• Molecular Formula: C9H8 O2 S2
• Molecular Weight: 212.293
• Hs Code.: 29309070
• European Community (EC) Number: 213-393-0
• NSC Number: 68200,42331
• DSSTox Substance ID: DTXSID30240972
• Nikkaji Number: J114G
• Wikidata: Q72440073
• ChEMBL ID: CHEMBL457019
• Mol file: 942-91-6.mol

Synonyms:942-91-6;S-(Thiobenzoyl)thioglycolic acid;2-((Phenylcarbonothioyl)thio)acetic acid;2-(benzenecarbonothioylsulfanyl)acetic acid;Acetic acid, [(phenylthioxomethyl)thio]-;[(phenylcarbonothioyl)thio]acetic acid;Carboxymethyl dithiobenzoate;(Thiobenzoylthio)acetic acid;C9H8O2S2;Thiobenzoyl thioglycolate;((Phenylthioxomethyl)thio)acetic acid;Thiobenzoylsulfanylacetic acid;EINECS 213-393-0;Benzoic acid, dithio-, ester with mercaptoacetic acid;2-(benzenecarbothioylsulfanyl)acetic acid;2-(Benzothioylthio)acetic acid;Benzoic acid, carboxymethyl ester;[(phenylthioxomethyl)thio]acetic acid;Acetic acid, ((phenylthioxomethyl)thio)-;Benzoic acid, ester with mercaptoacetic acid;Acetic acid, 2-[(phenylthioxomethyl)thio]-;Maybridge4_003837;S-Thiobenzoylthioglycolic acid;SCHEMBL162936;Thiobenzoylsulfanyl-acetic acid;AMY897;CHEMBL457019;XBEIANFIOZTEDE-UHFFFAOYSA-;DTXSID30240972;(Benzothioylsulfanyl)acetic acid #;2-(benzothioylsulfanyl)acetic acid;HMS1531O09;C9-H8-O2-S2;NSC42331;NSC68200;CCG-51440;MFCD00004927;NSC 42331;NSC 68200;NSC-42331;NSC-68200;STK331992;2-(phenylcarbonothioylthio)acetic acid;AKOS000321343;CS-W014999;2-((Phenylcarbonothioyl)thio)aceticacid;S-(Thiobenzoyl)thioglycolic acid, 99%;[(phenylcarbonothioyl)sulfanyl]acetic acid;2-(benzenecarbonothioylsulfanyl)aceticacid;2-(Phenylcarbonothioylsulfanyl)acetic acid;AS-64489;BP-30120;Benzoic acid, dithio-, carboxymethyl ester;BB 0240785;FT-0633167;T2401;D77774;A844901;J-506228;SR-01000640736-1

Chemical Property of S-(Thiobenzoyl)thioglycolic acid

Chemical Property:

• Appearance/Colour: Dark red.
• Vapor Pressure: 2.63E-06mmHg at 25°C
• Melting Point: 125-127 ºC
• Boiling Point: 375.5 °C at 760 mmHg
• PKA: 2.91±0.10(Predicted)
• Flash Point: 180.9 °C
• PSA: 94.69000
• Density: 1.379 g/cm³
• LogP: 2.17990
• Storage Temp.: Store below +30°C.
• Solubility.: acetone: soluble25mg/mL, clear
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 211.99657184
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

99% ^*data from raw suppliers

S-(Thiobenzoyl)thioglycolic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=S)SCC(=O)O
• Uses: S-(Thiobenzoyl)thioglycolic acid ((thiobenzoylthio)acetic acid) was employed as reversible addition-fragmentation chain transfer (RAFT) agent during the copolymerization of styrene and divinylbenzene. It was also employed as chain-transfer agent for the RAFT polymerizations of styrene, methyl methacrylate and butyl acrylate.It may be used to synthesize the following:N-Thiobenzoyl-DL-threonine ethyl ester by reacting with DL-threonine.Thiobenzoic acid O-esters by reacting with alkoxides.N-Thiobenzoylamino acids by reacting with amino acids.

Technology Process of S-(Thiobenzoyl)thioglycolic acid

There total 21 articles about S-(Thiobenzoyl)thioglycolic acid 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: 72.0%

carbon disulfide (75-15-0,12122-00-8) + chloroacetic acid (79-11-8) + phenylmagnesium bromide (100-58-3) → Carboxymethyl dithiobenzoate (942-91-6)

Guidance literature:

carbon disulfide; phenylmagnesium bromide; In tetrahydrofuran; at 0 - 20 ℃; for 12h;

chloroacetic acid; With sodium carbonate; In tetrahydrofuran; water; at 90 ℃; for 24h;

DOI:10.24820/ark.5550190.p010.871

Reference yield: 62.0%

carbon disulfide (75-15-0,12122-00-8) + bromobenzene (108-86-1,52753-63-6) + chloroacetic acid (79-11-8) → Carboxymethyl dithiobenzoate (942-91-6)

Guidance literature:

bromobenzene; With iodine; magnesium; In tetrahydrofuran; at 40 ℃;

carbon disulfide; In tetrahydrofuran; at 20 ℃; for 2h;

chloroacetic acid; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 90 ℃; for 0.0833333h;

Reference yield: 50.0%

carbon disulfide (75-15-0,12122-00-8) + bromobenzene (108-86-1,52753-63-6) + bromoacetic acid (79-08-3) → Carboxymethyl dithiobenzoate (942-91-6)

Guidance literature:

bromobenzene; With iodine; magnesium; In tetrahydrofuran; at 80 ℃; for 2h;

carbon disulfide; In tetrahydrofuran; at 0 ℃;

bromoacetic acid; In tetrahydrofuran; at 20 - 100 ℃;

DOI:10.1007/s11095-009-9998-8

upstream raw materials:

Benzotrichlorid

benzyl chloride

bromoacetic acid

sodium monochloroacetic acid

Downstream raw materials:

Thiobenzmorpholid

N,N-dimethylthiobenzamide

phenyl-thiobenzoylamino-acetic acid

methyl N-(thiobenzoyl)glycinate

Refernces

• 1、 Meng, Beibei,Shi, Qian,Meng, Yuan,Chen, Jie,Cao, Weiguo,Wu, Xiaoyu. "Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors". supporting information. p. 5087 - 5092. Retrieved 2021/06/21.
• 2、 Chen, Shoujun,Sun, Lijun,Koya, Keizo,Tatsuta, Noriaki,Xia, Zhiqiang,Korbut, Timothy,Du, Zhenjian,Wu, Jim,Liang, Guiqing,Jiang, Jun,Ono, Mitsunori,Zhou, Dan,Sonderfan, Andrew. "Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol". . p. 5070 - 5076. Retrieved 2013/09/12.