4-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Base Information

• Chemical Name: 4-Isothiocyanato-2-(trifluoromethyl)benzonitrile
• CAS No.: 143782-23-4
• Molecular Formula: C9H3F3N2S
• Molecular Weight: 228.197
• Hs Code.: 2930909090
• European Community (EC) Number: 700-928-2,691-294-5
• UNII: HP6388MX6K
• DSSTox Substance ID: DTXSID80932097
• Nikkaji Number: J1.788.372K
• Mol file: 143782-23-4.mol

Synonyms:143782-23-4;4-isothiocyanato-2-(trifluoromethyl)benzonitrile;4-cyano-3-(trifluoromethyl)phenyl isothiocyanate;4-cyano-3-trifluoromethylphenylisothiocyanate;Benzonitrile, 4-isothiocyanato-2-(trifluoromethyl)-;4-Cyano-3-(trifluoromethyl)phenylisothiocyanate;MFCD09800709;HP6388MX6K;4-isothiocyanato-2-trifluoromethylbenzonitrile;Enzalutamide Impurity 2;EC 700-928-2;UNII-HP6388MX6K;SCHEMBL189787;DTXSID80932097;AMY36836;CS-M0346;AKOS014821555;AC-31313;AS-10208;SY039781;I0987;NS00006823;4-isothiocyanato-2-trifluoromethyl benzonitrile;4-Isothiocyanato-2-trifluoromethyl-benzonitrile;2-(trifluoromethyl)-4-isothiocyanatobenzonitrile;EN300-6736481;4-isothiocyanato 2-(triflouromethyl)-benzonitrile;A850064;Isothiocyanic Acid 4-Cyano-3-(trifluoromethyl)phenyl Ester

Chemical Property of 4-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Chemical Property:

• Melting Point: 39.0 to 43.0 °C
• Boiling Point: 330.594 °C at 760 mmHg
• Flash Point: 153.738 °C
• PSA: 68.24000
• Density: 1.317 g/cm³
• LogP: 3.31138
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 227.99690376
• Heavy Atom Count: 15
• Complexity: 324

Purity/Quality:

97.0% ^*data from raw suppliers

4-Cyano-3-trifluoromethylphenylisothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1N=C=S)C(F)(F)F)C#N
• Uses: 4-Isothiocyanoyl-2-(trifluoromethyl)benzonitrile is a reagent used to synthesize thioimidazolinone compounds and is a potential anti-prostate cancer drug. It is also used as an intermediate of enzalutamide. 4-Cyano-3-trifluoromethylphenylisothiocyanate is an reagent used in the synthesis of thioxoimidazolidinones as potential anti-prostate cancer agents.

Technology Process of 4-Isothiocyanato-2-(trifluoromethyl)benzonitrile

There total 10 articles about 4-Isothiocyanato-2-(trifluoromethyl)benzonitrile 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: 100.0%

thiophosgene (463-71-8) + 4-amino-2-trifluoromethylbenzonitrile (654-70-6) → 4-isothiocyanato 2-(trifluoromethyl)benzonitrile (143782-23-4)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1021/acsmedchemlett.1c00032

Reference yield: 95.1%

1-[4-cyano-3-(trifluoromethyl)phenyl]thiourea → 4-isothiocyanato 2-(trifluoromethyl)benzonitrile (143782-23-4)

Guidance literature:

With potassium hydrogensulfate; In n-heptane; at 98 ℃; for 7h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 84.9%

4-isocyanate-2-(trifluoromethyl)benzonitrile toluene → 4-isothiocyanato 2-(trifluoromethyl)benzonitrile (143782-23-4)

Guidance literature:

With Lawessons reagent; at 35 ℃; for 4.5h; Temperature;

upstream raw materials:

thiophosgene

4-amino-2-trifluoromethylbenzonitrile

1,1'-Thiocarbonyldiimidazole

Downstream raw materials:

tert-butyl 3-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propylsulfonyl(methyl)carbamate

N,N-bis(4-methoxybenzyl)-2-[3-(4-cyano-3-trifluoromethylphenyl)-4-imino-5,5-dimethyl-2-thioxoimidazolidin-1-yl]ethanesulfonamide

4-[4,4-dimethyl-3-(3-hydroxypropyl)-5-imino-2-thioxo-1-imidazolidinyl]-2-trifluoromethyl-benzonitrile

N-Desmethylenzalutamide

Refernces

• 1、 Ferla, Salvatore,Bassetto, Marcella,Pertusati, Fabrizio,Kandil, Sahar,Westwell, Andrew D.,Brancale, Andrea,McGuigan, Christopher. "Rational design and synthesis of novel anti-prostate cancer agents bearing a 3,5-bis-trifluoromethylphenyl moiety". . p. 3636 - 3640. Retrieved 2016.
• 2、 Bachmaier, Rafael D.,Baltes, Fabian,Bendas, Gerd,Gütschow, Michael,Gockel, Lukas M.,Pfeifer, Vladlena,Sosi?, Izidor,Steinebach, Christian,Wagner, Karl G.. "Design, synthesis, and characterization of PROTACs targeting the androgen receptor in prostate and lung cancer models". . . Retrieved 2022/02/16.
• 3、 Wang, Ao,Wang, Yawan,Meng, Xin,Yang, Yushe. "Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer". . . Retrieved 2021/01/07.