Benzyl Isothiocyanate
Basic information
- CAS
622-78-6- Standard SMILES
S=C=NCc1ccccc1- InChIKey
MDKCFLQDBWCQCV-UHFFFAOYSA-N- Molecular formula
- C8H7NS
- Average molar mass
- 149.21 g/mol
- Monoisotopic mass
- 149.0299204
Overview
Benzyl isothiocyanate is a member of benzenes and an isothiocyanate. It has a role as an antibacterial drug.
Names & identifiers
- Preferred name
- Benzyl Isothiocyanate
- IUPAC
- isothiocyanatomethylbenzene
- English name
- Benzyl isothiocyanate
- Molecular formula
- C8H7NS
- Molecular weight
- 149.21
Names & synonyms
benzyl isothiocyanate622-78-6Benzylisothiocyanate(Isothiocyanatomethyl)benzeneBenzylsenfoelTromacapsTromalytUrogranBenzene, (isothiocyanatomethyl)-Isothiocyanic acid, benzyl esterisothiocyanatomethylbenzeneBITC
Show more names
1-(ISOTHIOCYANATOMETHYL)BENZENEAB 2NSC 118976benzylmustardoil
PMITC cpdphenylmethyl isothiocyanateDTXSID0020155871J6YOR8QNSC118976NSC-118976DTXCID60155FEMA NO. 4428
Database identifiers
- CAS
622-78-6- PubChem CID
- 2346
- DTXSID
DTXSID0020155- ChEMBL
CHEMBL55285- ChEBI
CHEBI:17484- UNII
- 871J6YOR8Q
- EC Number
- 210-753-9
- Nikkaji
- J6.842J
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 44.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 132
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
SpringerMaterials PropertiesBoiling point
LogP
3.16
3.16
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.121-1.127
Flavoring AgentsEU Flavoring substances
Solubility
0.109 mg/mL at 25 °C
Insoluble in water
Soluble (in ethanol)
Boiling Point
242.00 to 243.00 °C. @ 760.00 mm Hg
243 °C
Melting Point41 °C
Refractive Index1.600-1.606
Physical Description
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (99.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P261, P264+P265, P271, P280, P304+P340, P305+P351+P338, P319, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1426 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzene, (isothiocyanatomethyl)-
Benzene, (isothiocyanatomethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesEye Irrit. 2 (99.7%)
Safety data
- F
- 8-19-21
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NX8250000
- ridadr
- 2810
- hs_code
- 29309090
- Toxicity
- mmo-sat 150 mg/plate ABCHA6 44,3017,80
- risk_code
- 20/21/22-36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn,C,T
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationBenzene, (isothiocyanatomethyl)-: ACTIVE
Applications
OccurrenceReported found in common cress, Lepidium sativum, nasturtium, and Tropaeolum majus.
Usesantineoplastic, antibacterial, antifungal
UsesBenzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.
UsesA novel medical application of isothiocyanate ester in treating various leukemia, with low toxicity, which includes benzyl isothiocyanate, phenylethyl isothiocyanate, allyl isothiocyanate, sulforaphane, and erucin. Benzyl isothiocyanate (BITC) inhibits the growth of human pancreatic cancer cells by inducing apoptosis.
General DescriptionBenzyl 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.
Preparation methods
PreparationBenzyl isothiocyanate is synthesized by the following two methods: I) from Benzylamine via Thiuramdisulfide via Sodiumsalt with Iodine to Benzyl-isothiocyanate. 2) from Benzylamine and Thiocarbonyl chloride.
Related reactions
136 records
Compound notes
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