Benzyl Isothiocyanate (HCID 2346)

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

DTXSID0020155phenylmethyl isothiocyanatePMITC cpd871J6YOR8QNSC118976NSC-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 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 10
Formal charge: 0
Complexity: 132

Physicochemical properties

Melting point: 41 °C · 41 °C
Boiling point: 242 · 242-243 °C(lit.)
Density: 1.125 g/mL · 1.125 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.6018(lit.)
FEMA: 4428 · 4428 | BENZYL ISOTHIOCYANATE
FLAVIS Number: 12.102 · 12.102 | Benzyl isothiocyanate
Flash point: 235 °F · >235 °F
storage temp.: 2 · 2-8°C
solubility: 0.1 g/l · 0.1g/l
form: Liquid
Specific Gravity: 1.125 · 1.125
color: Clear yellow
Odor: 0.1 % · at 0.10 % in dipropylene glycol. mild watercress dusty medicinal horseradish oily
Odor Type: watercress
biological source: synthetic
Water Solubility: Hydrolyzes in water.
Sensitive: Moisture Sensitive
JECFA Number: 1562 · 1562
BRN: 386135 · 386135
Major Application: flavors and fragrances
InChI: 1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChIKey: MDKCFLQDBWCQCV-UHFFFAOYSA-N
SMILES: S=C=NCc1ccccc1
LogP: 3.16 · 3.16
CAS DataBase Reference: 622 · 622-78-6(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): BENZYL ISOTHIOCYANATE
FDA UNII: 871 J6YOR8Q · 871J6YOR8Q
EPA Substance Registry System: Benzene, (isothiocyanatomethyl)- (622-78-6)
UNSPSC Code: 85151701 · 85151701
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 302 · H302-H315-H317-H319-H334-H335
Precautionary statements: 261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn,C,T
Risk Statements: 20 · 20/21/22-36/37/38-42/43
Safety Statements: 26 · 26-36/37/39
RIDADR: 2810 · 2810
WGK Germany: 3 · 3
RTECS: 8250000 · NX8250000
F: 8 · 8-19-21
Hazard Note: Corrosive/Harmful/Store under nitrogen
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29309090 · 29309090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Toxicity: 150 mg/plate · mmo-sat 150 mg/plate ABCHA6 44,3017,80
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

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
hazard_note: Corrosive/Harmful/Store under nitrogen
safety_code: 26-36/37/39
hazard_class: 8
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H302-H315-H317-H319-H334-H335
Limited Quantities: 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements: P261-P264-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 5 items

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.