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Sigma-Aldrich

S-(Thiobenzoyl)thioglycolic acid

99%

Synonym(s):

(Thiobenzoylthio)acetic acid, Dithiobenzoic acid carboxymethyl ester

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About This Item

Linear Formula:
C6H5CS2CH2CO2H
CAS Number:
942-91-6
Molecular Weight:
212.29
EC Number:
213-393-0
MDL number:
MFCD00004927
UNSPSC Code:
12352100
PubChem Substance ID:
24849706
NACRES:
NA.22

Assay

99%

form

solid

mp

125-127 °C (lit.)

solubility

acetone: soluble 25 mg/mL, clear

SMILES string

OC(=O)CSC(=S)c1ccccc1

InChI

1S/C9H8O2S2/c10-8(11)6-13-9(12)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,11)

InChI key

XBEIANFIOZTEDE-UHFFFAOYSA-N

Related Categories

General description

S-(Thiobenzoyl)thioglycolic acid (TBTGA) also known as (thiobenzoylthio)acetic acid is a reagent used for thiobenzoylation. It participates in the transformation of threonine into β-methylcysteine.

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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(Thiocarbonyl-a-thio) carboxylic acid derivatives as transfer agents in reversible addition-fragmentation chain-transfer polymerizations.
Farmer SC and Patten TE.
Journal of Polymer Science Part A: Polymer Chemistry, 40(4), 555-563 (2002)
Copolymerization Kinetics of Styrene and Divinylbenzene in the Presence of S-Thiobenzoyl Thioglycolic Acid as RAFT Agent.
Roa-Luna M, et al.
Chemical Engineering & Technology, 33(11), 1893-1899 (2000)
Photochemical transformations. Part XXXI. Photolysis of thiobenzoic acid O-esters. Part II. General methods for the preparation of thiobenzoic acid O-esters.
Barton DHR, et al.
Journal of the Chemical Society. Perkin Transactions 1, 1571-1574 (1973)
Thiobenzoylation method of protein sequencing: gas chromatography/mass spectrometric detection of 5-acetoxy-2-phenylthiazoles.
Stolowitz ML, et al.
Methods in Protein Sequence Analysis, 37-44 (1993)
Synthesis of alpha-methyl- and beta-methyl-DL-cystine.
H R ARNSTEIN
The Biochemical journal, 68(2), 333-338 (1958-02-01)
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