3-(Trifluoromethyl)benzonitrile

Base Information

• Chemical Name: 3-(Trifluoromethyl)benzonitrile
• CAS No.: 368-77-4
• Molecular Formula: C8H4F3N
• Molecular Weight: 171.122
• Hs Code.: 29269095
• European Community (EC) Number: 206-711-4
• NSC Number: 88314
• UNII: Y7ZD7DK3AY
• DSSTox Substance ID: DTXSID4022026
• Nikkaji Number: J208.236E
• Wikidata: Q27294360
• ChEMBL ID: CHEMBL4472512
• Mol file: 368-77-4.mol

Synonyms:3-(Trifluoromethyl)benzonitrile;368-77-4;3-Cyanobenzotrifluoride;3-Trifluoromethylbenzonitrile;m-Trifluoromethylbenzonitrile;Benzonitrile, 3-(trifluoromethyl)-;alpha,alpha,alpha-Trifluoro-m-tolunitrile;a,a,a-trifluoro-m-tolunitrile;m-(Trifluoromethyl)benzonitrile;alpha,alpha,alpha-Trifluoro-m-toluonitrile;EINECS 206-711-4;UNII-Y7ZD7DK3AY;Y7ZD7DK3AY;3-trifluoromethyl-benzonitrile;a.a.a-Trifluoro-m-tolunitrile;NSC-88314;.alpha.,.alpha.,.alpha.-Trifluoro-m-tolunitrile;3-(Trifluoromehyl)benzonitrile;NSC88314;MFCD00001807;NCIOpen2_001287;SCHEMBL440276;CHEMBL4472512;DTXSID4022026;3-(CF3)-C6H4-CN;HMS1760C17;NSC 88314;STL163421;3-(Trifluoromethyl)benzonitrile, 99%;AKOS000119995;M-(TRIFLUOROMETHYL)CYANOBENZENE;AC-4111;PS-8692;1-CYANO-3-(TRIFLUOROMETHYL)BENZENE;LS-184873;AM20040296;CS-0059154;FT-0613932;FT-0615554;EN300-17572;W-106582;Q27294360;F0001-1058;M-TOLUNITRILE, .ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-

Chemical Property of 3-(Trifluoromethyl)benzonitrile

Chemical Property:

• Appearance/Colour: Colorless or light yellow liquid
• Vapor Pressure: 0.582mmHg at 25°C
• Melting Point: 16-20 °C(lit.)
• Refractive Index: n20/D 1.4575(lit.)
• Boiling Point: 189 °C at 760 mmHg
• Flash Point: 72.2 °C
• PSA: 23.79000
• Density: 1.29 g/cm³
• LogP: 2.57708
• Storage Temp.: 2-8°C
• Sensitive.: Lachrymatory
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 171.02958362
• Heavy Atom Count: 12
• Complexity: 200

Purity/Quality:

99% ^*data from raw suppliers

3-(Trifluoromethyl)-Benzonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)C(F)(F)F)C#N
• Uses: 3-(trifluoromethyl)-Benzonitrile is a useful chemical reagent. It has been employes in the validation of QSAR model for acute toxicity to the fathead minnow (Pimephales promelas). 3-(Trifluoromethyl)benzonitrile (α, α, α -trifluoro-m-tolunitrile) was used as a reference compound in the determination of the electron affinity of 1,3,5,7-cyclooctatetraene (COT).

Technology Process of 3-(Trifluoromethyl)benzonitrile

There total 57 articles about 3-(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: 89.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + potassiumhexacyanoferrate(II) trihydrate → 3-trifluoromethylbenzonitrile (368-77-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris(2-morpholinophenyl)phosphine; potassium carbonate; In water; tert-butyl alcohol; at 85 ℃; for 5h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c3ra43279c

Reference yield: 86.0%

potassiumhexacyanoferrate(II) trihydrate + 3-chlorotrifluoromethylbenzene (98-15-7) → 3-trifluoromethylbenzonitrile (368-77-4)

Guidance literature:

potassiumhexacyanoferrate(II) trihydrate; 3-chlorotrifluoromethylbenzene; With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate; In water; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

potassiumhexacyanoferrate(II) trihydrate; 3-chlorotrifluoromethylbenzene; With potassium carbonate; In water; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1007/s10562-021-03864-6

Reference yield: 84.0%

3-(trifluoromethyl)phenylacetone (21906-39-8) → 3-trifluoromethylbenzonitrile (368-77-4)

Guidance literature:

With aluminum (III) chloride; sodium nitrite; In N,N-dimethyl-formamide; at 120 ℃; for 4h; Schlenk technique;

DOI:10.1021/acs.orglett.5b03367

upstream raw materials:

3-trifluoromethylaniline

benzene-1,3-dicarbonitrile

ethanedinitrile

α,α,α-trifluorotoluene

Downstream raw materials:

2-(3-trifluoromethyl-phenyl)-4,5-dihydro-1H-imidazole

2-(pentafluoroethyl)-4,4-bis(trifluoromethyl)-6-{(3-trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine

2,4,4-Tris(trifluoromethyl)-6-{3-(trifluoromethyl)phenyl}-4H-1,3,5-oxadiazine

N-acetyl-3-trifluoromethylbenzenamine

Refernces

• 1、 Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi. "Nitrile Synthesis via Desulfonylative-Smiles Rearrangement". . p. 4460 - 4467. Retrieved 2022/03/15.
• 2、 Chen, Hua,Fu, Haiyan,Ji, Li,Li, Ruixiang,Nie, Xufeng,Zheng, Yanling. "Acceptorless dehydrogenation of amines to nitriles catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated bimetallic ruthenium (II) complex". . p. 378 - 385. Retrieved 2020/10/02.