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252492

Sigma-Aldrich

Benzyl isothiocyanate

98%

Sinonimo/i:

Benzyl mustard oil, Isothiocyanotaomethylbenzene

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About This Item

Formula condensata:
C6H5CH2NCS
Numero CAS:
622-78-6
Peso molecolare:
149.21
Beilstein:
386135
Numero CE:
210-753-9
Numero MDL:
MFCD00004819
Codice UNSPSC:
12352100
ID PubChem:
24855213
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Stato

liquid

Indice di rifrazione

n20/D 1.601 (lit.)

P. ebollizione

242-243 °C (lit.)

Densità

1.125 g/mL at 25 °C (lit.)

Gruppo funzionale

amine
isothiocyanate
phenyl

Temperatura di conservazione

2-8°C

Stringa SMILE

S=C=NCc1ccccc1

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H315,H317,H319,H334,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

222.8 °F

Punto d’infiammabilità (°C)

106 °C

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
STBK3105
STBH0563
STBG3986V
STBF4091V
STBD0644V

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Supelco

36682

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4-Chlorophenyl isothiocyanate 99%

Sigma-Aldrich

253782

4-Chlorophenyl isothiocyanate

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)
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
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)
Sanjay K Srivastava et al.
Carcinogenesis, 25(9), 1701-1709 (2004-05-01)
Benzyl isothiocyanate (BITC), a cruciferous vegetable-derived compound, has been shown to inhibit chemically induced cancer in animal models. Moreover, epidemiological studies have provided compelling evidence to suggest that cruciferous vegetables may be protective against cancer risk. Here, we report that
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