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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

Quality Level

100

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Imahori K and Sakiyama F.
Methods in Protein Sequence Analysis, 42-44 (2013)
(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)
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