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13929

Sigma-Aldrich

Benzyl thiocyanate

≥95.0% (GC)

Synonym(s):

Benzyl rhodanide

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About This Item

Linear Formula:
C6H5CH2SCN
CAS Number:
3012-37-1
Molecular Weight:
149.21
Beilstein:
1859726
EC Number:
221-144-2
MDL number:
MFCD00001832
UNSPSC Code:
12352100
PubChem Substance ID:
57647122
NACRES:
NA.22

Assay

≥95.0% (GC)

form

solid

bp

230-235 °C (lit.)

mp

39-41 °C (lit.)
39-41 °C

solubility

diethyl ether: soluble 0.5 g/10 mL, clear to very faintly turbid, colorless to almost colorless

functional group

phenyl

storage temp.

2-8°C

SMILES string

N#CSCc1ccccc1

InChI

1S/C8H7NS/c9-7-10-6-8-4-2-1-3-5-8/h1-5H,6H2

InChI key

ABNDFSOIUFLJAH-UHFFFAOYSA-N

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General description

Benzyl thiocyanate undergoes regioselective bond dissociation during its electrochemical reduction in acetonitrile at an inert electrode. It is added to stimulate the chlortetracycline biosynthesis during industrial fermentations. It undergoes biotransformation into dibenzyl disulphide by Streptomyces aureofaciens.

Application

Benzyl thiocyanate was used to study the effects of various dietary compounds on the α-hydroxylation of N-nitrosopyrrolidine in male F344 rats in vitro.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332,H412

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3

Supplementary Hazards

EUH032

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F

Flash Point(C)

110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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V Erban et al.
Folia microbiologica, 32(5), 411-416 (1987-01-01)
The localization of anhydrotetracycline oxygenase and glucose-6-phosphate dehydrogenase (EC 1.1.1.49) was studied by determining the enzyme activities in subcellular fractions obtained by differential centrifugation of the mycelia of Streptomyces aureofaciens after lysozyme treatment. Glucose-6-phosphate dehydrogenase was a typical cytoplasmic enzyme
S Sugie et al.
Carcinogenesis, 14(2), 281-283 (1993-02-01)
The effects of benzyl isothiocyanate (BITC) and benzyl thiocyanate (BTC) on two types of DNA synthesis were examined in hepatocyte primary cultures (HPC). Male F344 rats were fed BITC- or BTC-containing diets at a concentration of 400 p.p.m. Using hepatocytes
X M Li et al.
Applied microbiology and biotechnology, 57(5-6), 717-724 (2002-01-10)
Changes in synthesis and abundance of proteins associated with chlortetracycline (CTC) production in Streptomyces aureofaciens were investigated by two-dimensional polyacrylamide gel electrophoresis of proteins pulse-labelled in vivo with L-[35S]methionine. Eleven individual protein spots were selected as being related to formation
V Bĕhal et al.
Folia microbiologica, 27(2), 102-106 (1982-01-01)
The level of anhydrotetracyline oxygenase (an enzyme catalyzing the penultimate reaction in the biosynthesis of tetracyline) in Streptomyces aureofaciens was substantially influenced by the amount of inorganic phosphate and by the presence of benzyl thiocyanate in the cultivation medium. Phosphate
L V Trilisenko et al.
Folia microbiologica, 32(5), 402-410 (1987-01-01)
Mycelia of a low- and a high-production strain of Streptomyces aureofaciens were converted into protoplasts and divided into five subcellular fractions in order to localize exopolyphosphatases (EC 3.6.1.11), triphosphatase (EC 3.6.1.25), inorganic diphosphatase (EC 3.6.1.1), apyrase (EC 3.6.1.5) and glucokinase
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