4-Amino-2-(trifluoromethyl)benzonitrile

Base Information

• Chemical Name: 4-Amino-2-(trifluoromethyl)benzonitrile
• CAS No.: 654-70-6
• Molecular Formula: C8H5F3N2
• Molecular Weight: 186.136
• Hs Code.: 29049090
• European Community (EC) Number: 700-293-1,613-800-5
• UNII: L47D9XHC08
• DSSTox Substance ID: DTXSID80215711
• Nikkaji Number: J254.886K
• Wikipedia: 4-Cyano-3-(trifluoromethyl)aniline
• Wikidata: Q27282680
• Mol file: 654-70-6.mol

Synonyms:4-Amino-2-(trifluoromethyl)benzonitrile;654-70-6;5-Amino-2-cyanobenzotrifluoride;4-Cyano-3-trifluoromethylaniline;4-Amino-2-trifluoromethylbenzonitrile;2-cyano-5-aminobenzotrifluoride;Benzonitrile, 4-amino-2-(trifluoromethyl)-;4-cyano-3-(trifluoromethyl)aniline;2-trifluoromethyl-4-aminobenzonitrile;Bicalutamide aminobenzonitrile;5-Amino-2-cyanobenzotrifluoride-d3;UNII-L47D9XHC08;Bicalutamide impurity D [EP];L47D9XHC08;MFCD00042155;EC 700-293-1;4-Amino-alpha,alpha,alpha-trifluoro-o-tolunitrile;o-Tolunitrile, 4-amino-alpha,alpha,alpha-trifluoro-;4-Amino 2-trifluoromethyl benzonitrile;4-amino-2-trifluoromethyl benzonitrile;Bicalutamide Impurity D;SCHEMBL110567;5-amino2-cyanobenzotrifluoride;4-cyano-3-trifluoromethylanilin;5-Aminno-2-cyanobenzotrifluoride;PMDYLCUKSLBUHO-UHFFFAOYSA-;DTXSID80215711;PC1070L;3-trifluoromethyl-4-cyano-aniline;4-cyano-3-trifluoromethyl-aniline;BCP01007;CS-M3188;STL480835;4-Amino-2-trifluromethyl benzonitrile;4-amino-2-trifluoromethyl-benzonitrile;AKOS005063751;AB01894;AC-4021;PS-8479;4-Amino-2-(trifluoromethyl)benzonitrile #;(2R)-2-Hydroxyglutaric Acid Disodium Salt;A1213;A8877;AM20040963;BICALUTAMIDE IMPURITY D [EP IMPURITY];FT-0619978;FT-0652695;EN300-92112;4-Amino-2-(trifluoromethyl)benzonitrile, 97%;Q-100744;Q27282680;Z381080278;4-AMINO-.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-O-TOLUNITRILE;O-TOLUNITRILE, 4-AMINO-.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-

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

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.00162mmHg at 25°C
• Melting Point: 136-145 °C
• Refractive Index: 1.499
• Boiling Point: 294.5 °C at 760 mmHg
• PKA: 0.50±0.10(Predicted)
• Flash Point: 131.9 °C
• PSA: 49.81000
• Density: 1.37 g/cm³
• LogP: 2.74048
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 186.04048265
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-2-cyanobenzotrifluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-43-36/37/38-20/21/22
• Safety Statements: 36-45-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1N)C(F)(F)F)C#N
• Uses: 4-Amino-2-(trifluoromethyl)benzonitrile is used for the preparation of benzene derivatives as non-steroidal androgen receptor modulators. 4-Amino-2-(trifluoromethyl)benzonitrile can serve as starting material in the synthesis of benzimidazoles, which can act as potential candidates in the treatment of breast cancer due to their ability to inhibit the growth of endothelial cells.

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

There total 15 articles about 4-Amino-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: 98.9%

4-amino-2-(trifluoromethyl)benzaldehyde (876322-73-5) → 4-amino-2-trifluoromethylbenzonitrile (654-70-6)

Guidance literature:

With ammonium bisulphate; acetic acid; In toluene; for 16h; Solvent; Reflux;

Reference yield: 92.0%

4-amino-2-trifluoromethylbenzamide (934600-95-0) → 4-amino-2-trifluoromethylbenzonitrile (654-70-6)

Guidance literature:

With thionyl chloride; In toluene; at 60 ℃; for 5h; Temperature; Solvent;

Reference yield: 91.0%

zinc(II) cyanide (557-21-1) + 3-(trifluoromethyl)-4-iodobenzenamine (155403-06-8) → 4-amino-2-trifluoromethylbenzonitrile (654-70-6)

Guidance literature:

With C₁₂H₁₀N^(1-)*CH₃O₃S^(1-)*Pd⁽²⁺⁾*C₃₉H₃₂OP₂; In tetrahydrofuran; water; at 65 ℃; for 16h; Micellar solution;

DOI:10.1002/cctc.202001742

upstream raw materials:

4-chloro-2-(trifluoromethyl)benzonitrile

copper(I) cyanide

4-bromo-3-(trifluoromethyl)aniline

C₁₀H₇F₃N₂O

Downstream raw materials:

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[phenylthio]-2-hydroxy-2-methyl-propanamide

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide

N₁-[4-cyano-3-(trifluoromethyl)phenyl]-(2R)-3-[(4-aminophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

N₁-[4-cyano-3-(trifluoromethyl)phenyl]-(2S)-3-[(4-aminophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Refernces

• 1、 Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.. "High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates". supporting information. p. 8114 - 8118. Retrieved 2021/10/25.
• 2、 -. "Preparation method of 4-amino-2-trifluoromethyl benzonitrile". . . Retrieved 2020/05/14.