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B25401

Sigma-Aldrich

Benzyl mercaptan

99%

Synonym(s):

α-Toluenethiol, α-Tolyl mercaptan, Benzenemethanethiol

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About This Item

Linear Formula:
C6H5CH2SH
CAS Number:
100-53-8
Molecular Weight:
124.20
Beilstein/REAXYS Number:
605864
EC Number:
202-862-5
MDL number:
MFCD00004867
UNSPSC Code:
12352100
PubChem Substance ID:
24891657
NACRES:
NA.22

vapor density

>4 (vs air)

assay

99%

form

liquid

refractive index

n20/D 1.575 (lit.)

bp

194-195 °C (lit.)

density

1.058 g/mL at 25 °C (lit.)

SMILES string

SCc1ccccc1

InChI

1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

InChI key

UENWRTRMUIOCKN-UHFFFAOYSA-N

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Application

Benzyl mercaptan can be used as:
  • A nucleophilic reagent in the cleavage of proanthocyanidins into their constitutive subunits.
  • A reactant in the synthesis of dithiocarboxylic esters in the presence of phosphorus pentasulfide as a catalyst.
  • A modifier to functionalize the surface of CNT for enhanced interaction with Pt-nanoparticles.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol.
Kennedy JA and Jones GP
Journal of Agricultural and Food Chemistry, 49(4), 1740-1746 (2001)
Strongly enhanced interaction between evaporated Pt nanoparticles and functionalized multiwalled carbon nanotubes via plasma surface modifications: Effects of physical and chemical defects.
Yang DQ and Sacher E
The Journal of Physical Chemistry C, 112(11), 4075-4082 (2008)
Phosphorus pentasulfide: A mild and versatile catalyst/reagent for the preparation of dithiocarboxylic esters.
Sudalai A, et al.
Organic Letters, 2(20), 3213-3216 (2000)
Kenji Matsuno et al.
Bioorganic & medicinal chemistry letters, 20(17), 5126-5129 (2010-08-07)
S-benzylisothiourea 3a was discovered by its ability to inhibit indoleamine-2,3-dioxygenase (IDO) in our screening program. Subsequent optimization of the initial hit 3a lead to the identification of sub-muM inhibitors 3r and 10h, both of which suppressed kynurenine production in A431
Theresa K Tiefenbrunn et al.
Protein science : a publication of the Protein Society, 18(5), 970-979 (2009-04-23)
The type 1 repeat domain from thrombospondin has potent antiangiogenic activity and a structurally interesting fold, making it an attractive target for protein engineering. Chemical synthesis is an attractive approach for studying protein domains because it enables the use of
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