Phenethyl isothiocyanate

Base Information

• Chemical Name: Phenethyl isothiocyanate
• CAS No.: 2257-09-2
• Molecular Formula: C9H9NS
• Molecular Weight: 163.243
• Hs Code.: 29309090
• European Community (EC) Number: 218-855-5
• NSC Number: 87868
• UNII: 6U7TFK75KV
• DSSTox Substance ID: DTXSID5021120
• Nikkaji Number: J41.504I
• Wikipedia: Phenethyl_isothiocyanate
• Wikidata: Q7181339
• NCI Thesaurus Code: C2233
• Pharos Ligand ID: YGFQ82TXHLUS
• Metabolomics Workbench ID: 48202
• ChEMBL ID: CHEMBL151649
• Mol file: 2257-09-2.mol

Synonyms:2-phenylethyl isothiocyanate;beta-phenylethyl isothiocyanate;PEITC;phenethyl isothiocyanate;phenethylisothiocyanate;phenylethyl isothiocyanate

Chemical Property of Phenethyl isothiocyanate

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Vapor Pressure: 0.0427mmHg at 25°C
• Melting Point: 143～145℃
• Refractive Index: n20/D 1.5888(lit.)
• Boiling Point: 278.089 °C at 760 mmHg
• Flash Point: 124.408 °C
• PSA: 44.45000
• Density: 1.007 g/cm³
• LogP: 2.33190
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Sensitive.: Moisture Sensitive
• Water Solubility.: insoluble
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 163.04557046
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

2-Phenylethyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42-42/43
• Safety Statements: 23-26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Isothiocyanates
• Canonical SMILES: C1=CC=C(C=C1)CCN=C=S
• Recent ClinicalTrials: Phenethyl Isothiocyanate in Preventing Lung Cancer in Smokers
• Description: Phenethyl isothiocyanate is a naturally occurring isothiocyanate in cruciferous vegetables. Phenethyl isothiocyanate is a chemopreventive agent. It inhibits cancer cell growth by arresting the cell cycle and inducing apoptosis in various human cancer cell models.
• Uses: Flavor ingredient; provides the hot or burning sensation in horseradish. Phenethyl isothiocyanate (PEITC)，one of the major compounds from dietary cruciferousvegetables，has been found to have antitumor properties and therefore could generate special interest for the development of chemopreventive andor chemotherapeutic agent for human cancers. Phenethyl isothiocyanate is an NNK-induced lung tumorigenesis inhibitor.

Technology Process of Phenethyl isothiocyanate

There total 41 articles about Phenethyl 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: 83.0%

Triethylammonium-(2-phenylethyl)dithiocarbamat (24954-65-2) → Phenethyl isothiocyanate (2257-09-2)

Guidance literature:

With sodium persulfate; potassium carbonate; In water; at 20 ℃; for 1h; chemoselective reaction; Green chemistry;

DOI:10.1039/c8gc02261e

Reference yield: 83.0%

ammonium thiocyanate + 2-phenylethanol (60-12-8) → Phenethyl isothiocyanate (2257-09-2) + 2-phenylethyl thiocyanate (5654-72-8)

Guidance literature:

ammonium thiocyanate; With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate); In acetonitrile; at 20 ℃; for 0.333333h;

2-phenylethanol; In acetonitrile; for 0.583333h;

DOI:10.1016/j.jfluchem.2012.03.005

Reference yield: 74.0%

trifluoromethane sulfonyl chloride (421-83-0) + phenethylamine (64-04-0) → Phenethyl isothiocyanate (2257-09-2)

Guidance literature:

With triphenylphosphine; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01634

upstream raw materials:

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

sodium ethanolate

carbon disulfide

phenethylamine

Downstream raw materials:

N-(phenethyl)-N'-(phenethyl)thiourea

(hexahydro-pyrido[1,2-c][1,3]thiazin-1-ylidene)-phenethyl-amine

1-(4,5-dihydro-thiazol-2-yl)-1,3-diphenethyl-thiourea

N-phenethyl O-ethyl thiocarbamate

Refernces

• 1、 Ray, Ujjayinee,John, Franklin,Pooppadi, Sayeesh,George, Jinu,Sharma, Shivangi,Raghavan, Sathees C. "Novel synthetic aromatic thiourea derivatives and investigations on their cytotoxic potential efficacy". . p. 40 - 47. Retrieved 2020/09/21.
• 2、 Fan, Jing,Feng, Jing,Franklin, G. Joseph,Lancia, David R.,Li, Jin,Liu, Guansai,O'connell, Jonathan,Peng, Ting,Su, Liqiang,Wan, Jinqiao. "Synthesis of Multifunctional 2-Aminobenzimidazoles on DNA via Iodine-Promoted Cyclization". supporting information. . Retrieved 2020/02/13.