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252492

Sigma-Aldrich

Benzyl isothiocyanate

98%

Synonym(s):

Benzyl mustard oil, Isothiocyanotaomethylbenzene

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About This Item

Linear Formula:
C6H5CH2NCS
CAS Number:
622-78-6
Molecular Weight:
149.21
Beilstein/REAXYS Number:
386135
EC Number:
210-753-9
MDL number:
MFCD00004819
UNSPSC Code:
12352100
PubChem Substance ID:
24855213
NACRES:
NA.22

Quality Level

200

assay

98%

form

liquid

refractive index

n20/D 1.601 (lit.)

bp

242-243 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

S=C=NCc1ccccc1

InChI

1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2

InChI key

MDKCFLQDBWCQCV-UHFFFAOYSA-N

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General description

Benzyl isothiocyanate is a naturally-occurring constituent of cruciferous vegetables. It has antibacterial properties and its metabolism in man has been investigated. It inhibits chemically induced cancer in animal models.

Application

Benzyl isothiocyanate can be used as a reactant to synthesize:
  • N

  • -benzylthioureas by reacting with various amines.
  • N-benzyl-O-alkyl carbamates by treating with long-chain alcohols.
  • 3-mercapto-1,2,4-triazole building block by reacting with formylhydrazine via acyl thiosemicarbazide intermediate formation.
  • S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.

Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

222.8 °F

flash_point_c

106 °C

ppe

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

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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A Simple and Green Procedure for the Synthesis of N-Benzylthioureas
C de Sequeira Aguiar L, et al.
Letters in Organic Chemistry, 8(8), 540-544 (2011)
G Brüsewitz et al.
The Biochemical journal, 162(1), 99-107 (1977-01-15)
1. The corresponding cysteine conjugate was formed when the GSH (reduced glutathione) or cysteinylglycine conjugates of benzyl isothiocyanate were incubated with rat liver or kidney homogenates. When the cysteine conjugate of benzyl isothiocyanate was similarly incubated in the presence of
Synthesis of 5-substituted 3-mercapto-1, 2, 4-triazoles via Suzuki-Miyaura reaction
Katkevica S, et al.
Tetrahedron Letters, 54(34), 4524-4525 (2013)
Shahnaz Perveen et al.
Natural product research, 24(1), 18-23 (2009-12-17)
The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols
W H Mennicke et al.
Xenobiotica; the fate of foreign compounds in biological systems, 18(4), 441-447 (1988-04-01)
1. Both after ingestion of benzyl isothiocyanate (BITC), a compound with antibacterial properties, and after consumption of garden cress known to contain BITC, the metabolite N-acetyl-S-(N-benzylthiocarbamoyl)-L-cysteine was identified in the urine of volunteers by comparative chromatography. 2. The chemical structure
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