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157880

Sigma-Aldrich

S-(Thiobenzoyl)thioglycolic acid

99%

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Synonym(s):
(Thiobenzoylthio)acetic acid, Dithiobenzoic acid carboxymethyl ester
Linear Formula:
C6H5CS2CH2CO2H
CAS Number:
Molecular Weight:
212.29
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
T3758D6518T6750
S-(Thiobenzoyl)thioglycolic acid 99%

157880

S-(Thiobenzoyl)thioglycolic acid

Thioglycolic acid 98%

T3758

Thioglycolic acid

Diethylenetriaminepentaacetic acid ≥99% (titration)

D6518

Diethylenetriaminepentaacetic acid

Thioglycolic acid solution ~70 % (w/w) in H2O

T6750

Thioglycolic acid solution

solubility

acetone: soluble 25 mg/mL, clear

solubility

-

solubility

1 M HCl: 50 mg/mL, clear, colorless

solubility

-

mp

125-127 °C (lit.)

mp

−16 °C (lit.)

mp

219-220 °C (lit.)

mp

-

form

solid

form

liquid

form

powder

form

-

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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Customers Also Viewed

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

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