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252492

Sigma-Aldrich

Benzyl isothiocyanate

98%

Synonym(s):

Benzyl mustard oil, Isothiocyanotaomethylbenzene

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5 G
€39.60
25 G
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About This Item

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

€39.60

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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.)

functional group

amine
isothiocyanate
phenyl

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[1]. It has antibacterial properties and its metabolism in man has been investigated[2]. It inhibits chemically induced cancer in animal models[1].

Application

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

  • -benzylthioureas by reacting with various amines.[3]
  • N-benzyl-O-alkyl carbamates by treating with long-chain alcohols.[4]
  • 3-mercapto-1,2,4-triazole building block by reacting with formylhydrazine via acyl thiosemicarbazide intermediate formation.[5]
  • S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.[6]

Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine[6].

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

222.8 °F

Flash Point(C)

106 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK3105
STBH0563
STBG3986V
STBF4091V
STBD0644V

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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)
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
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)
Su-Hua Huang et al.
Journal of agricultural and food chemistry, 60(2), 665-675 (2011-12-14)
Benzyl isothiocyanates (BITC), a member of the isothiocyanate (ITC) family, inhibits cell growth and induces apoptosis in many types of human cancer cell lines. The present study investigated mechanisms underlying BITC-induced apoptosis in A375.S2 human melanoma cancer cells. To observe
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
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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