Benzyl Isothiocyanate
BITC · (Isothiocyanatomethyl)benzene · Urogran · 1-(ISOTHIOCYANATOMETHYL)BENZENE · AB 2 · Tromalyt · Tromacaps · NSC 118976
Identifiers & Physical Properties
| CAS No. | 622-78-6 |
|---|---|
| Molecular formula | C8H7NS |
| Average molar mass | 149.21 g/mol |
| Monoisotopic mass | 149.0299204 g/mol |
| SMILES | S=C=NCc1ccccc1 |
| InChIKey | MDKCFLQDBWCQCV-UHFFFAOYSA-N |
| PubChem CID | 2346 |
| ChEMBL | CHEMBL55285 |
| ChEBI | CHEBI:17484 |
| EC No. | 210-753-9 |
| DTXSID | DTXSID0020155 |
Chemical & Physical Properties
| XLogP | 3.2 |
|---|---|
| Topological polar surface area | 44.5 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 132 |
| Melting point | 41 °C |
| Boiling point | 242-243 °C(lit.) |
| Density | 1.125 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.6018(lit.) |
| FEMA | 4428 | BENZYL ISOTHIOCYANATE |
| FLAVIS Number | 12.102 | Benzyl isothiocyanate |
| Flash point | >235 °F |
| Storage conditions | 2-8°C |
| Solubility | 0.1g/lHydrolyzes in water. |
| Physical state | Liquid |
| Specific gravity | 1.125 |
| Color | Clear yellow |
| Odor | at 0.10 % in dipropylene glycol. mild watercress dusty medicinal horseradish oily |
| Odor type | watercress |
| Biological source | synthetic |
| Sensitivity | Moisture Sensitive |
| JECFA Number | 1562 |
| BRN | 386135 |
| Major applications | 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 (partition coefficient) | 3.16 |
| CAS DataBase Reference | 622-78-6(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | BENZYL ISOTHIOCYANATE |
| FDA UNII | 871J6YOR8Q |
| EPA Substance Registry System | Benzene, (isothiocyanatomethyl)- (622-78-6) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H302-H315-H317-H319-H334-H335 |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,C,T |
| Risk statements (R) | 20/21/22-36/37/38-42/43 |
| Safety statements (S) | 26-36/37/39 |
| UN transport number | 2810 |
| Water hazard class (WGK) | 3 |
| RTECS number | NX8250000 |
| F | 8-19-21 |
| Hazard Note | Corrosive/Harmful/Store under nitrogen |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Packing group | III |
| Customs code | 29309090 |
| Storage class | 10 - Combustible liquids |
| Toxicity | mmo-sat 150 mg/plate ABCHA6 44,3017,80 |
| 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) |
Safety & Regulations
| F | 8-19-21 |
|---|---|
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | NX8250000 |
| UN transport number | 2810 |
| Customs code | 29309090 |
| Toxicity | mmo-sat 150 mg/plate ABCHA6 44,3017,80 |
| Risk statements (R) | 20/21/22-36/37/38-42/43 |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xn,C,T |
| hazard_note | Corrosive/Harmful/Store under nitrogen |
| Safety statements (S) | 26-36/37/39 |
| Hazard class | 8Acute Tox. 4 OralEye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Storage class | 10 - Combustible liquids |
| Packing group | III |
| Target organs | Respiratory system |
| GHS 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) |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
Applications & Uses
Occurrence
Reported found in common cress, Lepidium sativum, nasturtium, and Tropaeolum majus.
Uses
antineoplastic, antibacterial, antifungal
Uses
Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.
Uses
A 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 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.
Preparation & Synthesis
Preparation
Benzyl 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.