4-Amino-3-trifluoromethylbenzonitrile

Base Information

• Chemical Name: 4-Amino-3-trifluoromethylbenzonitrile
• CAS No.: 327-74-2
• Molecular Formula: C8H5F3N2
• Molecular Weight: 186.136
• Hs Code.: 2926909090
• European Community (EC) Number: 675-039-5
• DSSTox Substance ID: DTXSID70381459
• Nikkaji Number: J2.931.915D
• Wikidata: Q72435050
• Mol file: 327-74-2.mol

Synonyms:327-74-2;4-amino-3-(trifluoromethyl)benzonitrile;4-AMINO-3-TRIFLUOROMETHYLBENZONITRILE;2-Amino-5-cyanobenzotrifluoride;2-trifluoromethyl-4-cyanoaniline;Benzonitrile, 4-amino-3-(trifluoromethyl)-;MFCD00275473;4-Cyano-2-(trifluoromethyl)aniline;SCHEMBL568905;DTXSID70381459;CL8205;4-amino-3-trifluoromethyl-benzonitrile;AKOS001304324;AC-1090;AM61479;CS-W016921;PS-8478;NCGC00336303-01;4-amino-3-(trifluoromethyl)benzoni-trile;SY018407;A2644;A5852;FT-0631960;EN300-24523;AB01129918-03;Z198766668;4-Amino-3-trifluoromethylbenzonitrile 2-Amino-5-cyanobenzotrifluoride

Chemical Property of 4-Amino-3-trifluoromethylbenzonitrile

Chemical Property:

• Melting Point: 60-63 °C
• Boiling Point: 273.9 °C at 760 mmHg
• PKA: -1.41±0.10(Predicted)
• Flash Point: 119.5 °C
• PSA: 49.81000
• Density: 1.697 g/cm³
• LogP: 2.74048
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), 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

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

Safty Information:

• Pictogram(s): Xi,T
• Hazard Codes: Xi,T
• Statements: 23/24/25-36/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)C(F)(F)F)N
• Uses: 2-Amino-5-cyanobenzotrifluoride is used in the design and synthesis of 4-phenylpyrrole derivatives as androgen receptor antagonists which show efficacy against prostate cancer cells.

Technology Process of 4-Amino-3-trifluoromethylbenzonitrile

There total 10 articles about 4-Amino-3-trifluoromethylbenzonitrile 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: 99.28%

dicyanozinc (557-21-1) + 4-iodo-2-(trifluoromethyl)aniline (97760-97-9) → 4-cyano-2-trifluoromethylaniline (327-74-2)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; for 12h;

Reference yield: 93.0%

4-bromo-2-trifluoromethyl-aniline (445-02-3) + copper(l) cyanide → 4-cyano-2-trifluoromethylaniline (327-74-2)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; at 200 ℃; for 5h; Inert atmosphere; Schlenk technique;

DOI:10.1002/asia.201600538

Reference yield: 81.0%

Togni's reagent II (887144-94-7) + 4-Aminobenzonitrile (873-74-5) → 4-cyano-2-trifluoromethylaniline (327-74-2)

Guidance literature:

With potassium carbonate; In acetonitrile; at 75 ℃; for 6h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151538

upstream raw materials:

dicyanozinc

4-iodo-2-(trifluoromethyl)aniline

4-bromo-2-trifluoromethyl-aniline

2-(trifluoromethyl)benzenamine

Downstream raw materials:

N-(4-cyano-2-trifluoromethylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

C₈H₉F₃N₂*ClH

Refernces

• 1、 Chen, Xiaoyu,Ding, Licheng,Li, Linlin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng. "Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent". supporting information. . Retrieved 2019/12/30.
• 2、 -. "Synthetic method of aminobenzotrifluoride and derivant thereof". Paragraph 0050; 0051; 0104. . Retrieved 2018/09/13.