Benzyl isothiocyanate

Base Information

• Chemical Name: Benzyl isothiocyanate
• CAS No.: 622-78-6
• Molecular Formula: C8H7NS
• Molecular Weight: 149.216
• Hs Code.: 29309090
• European Community (EC) Number: 210-753-9
• NSC Number: 758206,118976
• UNII: 871J6YOR8Q
• DSSTox Substance ID: DTXSID0020155
• Nikkaji Number: J6.842J
• Wikipedia: Benzyl_isothiocyanate
• Wikidata: Q18341725
• NCI Thesaurus Code: C68537
• Pharos Ligand ID: JNMR8F2JKVPQ
• Metabolomics Workbench ID: 46316
• ChEMBL ID: CHEMBL55285
• Mol file: 622-78-6.mol

Synonyms:Isothiocyanicacid, benzyl ester (6CI,8CI);(Isothiocyanatomethyl)benzene;1-(Isothiocyanatomethyl)benzene;Benzyl isothiocyanate;Benzyl mustardoil;NSC 118976;Phenylmethyl isothiocyanate;Tromacaps;Tromalyt;Urogran;

Chemical Property of Benzyl isothiocyanate

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 0.0491mmHg at 25°C
• Melting Point: 41 °C
• Refractive Index: n20/D 1.6018(lit.)
• Boiling Point: 243.8 °C at 760 mmHg
• Flash Point: 100.4 °C
• PSA: 44.45000
• Density: 1.02 g/cm³
• LogP: 2.28940
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: 0.1g/l
• Water Solubility.: Hydrolyzes in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 149.02992040
• Heavy Atom Count: 10
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

Benzyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,T
• Hazard Codes: Xn,C,T
• Statements: 20/21/22-36/37/38-42/43
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN=C=S
• Recent EU Clinical Trials: Impact of Exercise and Mediterranean diet vs Aspirin on live-birth rate and cardiovascular programming in In Vitro Fertilization (MEDITATE-IVF): a Randomized Study.
• 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. antineoplastic, antibacterial, antifungal Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.

Technology Process of Benzyl isothiocyanate

There total 85 articles about Benzyl isothiocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

carbon disulfide (75-15-0,12122-00-8) + benzylamine (100-46-9) → Benzyl isothiocyanate (622-78-6)

Guidance literature:

carbon disulfide; benzylamine; With potassium carbonate; In water; at 20 ℃; for 1h; Inert atmosphere;

With 1,3,5-trichloro-2,4,6-triazine; In dichloromethane; water; at 0 ℃; for 0.5h; Inert atmosphere;

With sodium hydroxide; In dichloromethane; water; pH=11; Inert atmosphere;

DOI:10.3762/bjoc.8.6

Reference yield: 98.0%

potassium thioacyanate (333-20-0) + benzyl chloride (100-44-7) → benzyl thiocyanate (3012-37-1) + Benzyl isothiocyanate (622-78-6)

Guidance literature:

bis-aza-crown II; In 1,2-dichloro-benzene; at 180 ℃; for 1.83333h;

Reference yield: 97.0%

triethylammonium N-benzyldithiocarbamate (43009-20-7) → Benzyl isothiocyanate (622-78-6)

Guidance literature:

With iodine; triethylamine; In acetonitrile; at 5 ℃; Cooling with ice;

DOI:10.1002/ejoc.200801270

upstream raw materials:

benzyl thiocyanate

4-benzylthiosemicarbazide

benzyl-dithiocarbamic acid propyl ester

μ-disulfido-1,2-dithio-dicarbonic acid bis-benzylamide

Downstream raw materials:

2-benzothiazol-2-ylimino-3-benzyl-5-methyl-thiazolidin-4-one

1-benzothiazol-2-yl-3-benzyl-thiourea

C₁₇H₁₇N₅OS₂

2,2,2-Tris-benzotriazol-1-yl-N-benzyl-thioacetamide

Refernces

• 1、 Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota. "Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent". . . Retrieved 2021/05/29.
• 2、 An, Zhenyu,Liu, Yafeng,Ren, Yi,Wang, Ting,Yan, Rulong. "A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts". supporting information. p. 6206 - 6209. Retrieved 2021/07/28.