4-(Trifluoromethoxy)benzonitrile

Base Information

• Chemical Name: 4-(Trifluoromethoxy)benzonitrile
• CAS No.: 332-25-2
• Molecular Formula: C8H4F3NO
• Molecular Weight: 187.121
• Hs Code.: 29269090
• European Community (EC) Number: 206-363-3
• DSSTox Substance ID: DTXSID5073163
• Nikkaji Number: J193.762F
• Wikidata: Q72511311
• Mol file: 332-25-2.mol

Synonyms:4-(Trifluoromethoxy)benzonitrile

Chemical Property of 4-(Trifluoromethoxy)benzonitrile

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 0.624mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 192.5 °C at 760 mmHg
• Flash Point: 82.8 °C
• PSA: 33.02000
• Density: 1.34 g/cm³
• LogP: 2.45688
• Storage Temp.: Room temperature.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 187.02449824
• Heavy Atom Count: 13
• Complexity: 209

Purity/Quality:

98% ^*data from raw suppliers

4-(Trifluoromethoxy)benzonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)OC(F)(F)F

Technology Process of 4-(Trifluoromethoxy)benzonitrile

There total 32 articles about 4-(Trifluoromethoxy)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: 98.0%

N-hydroxy-1-[4-(trifluoromethoxy)phenyl]methaneimine (150162-39-3) → 4-(trifluoromethoxy)benzonitrile (332-25-2)

Guidance literature:

With 1,1,3,3-tetraphenyl-2-oxa-1,3-phoshpinobenzene bis(trifluoromethanesulfonate); triethylamine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1055/s-0031-1289998

Reference yield: 95.5%

4-trifluoromethoxybenzyl alcohol (1736-74-9) → 4-(trifluoromethoxy)benzonitrile (332-25-2) + 4-trifluoromethoxybenzamide (456-71-3)

Guidance literature:

With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 4h; under 3750.38 Torr; Overall yield = > 99 percent; Autoclave; High pressure;

DOI:10.1021/acscatal.0c00485

Reference yield: 93.0%

2-(dimethylamino)malononitrile (19555-13-6) + 1-iodo-4-(trifluoromethoxy)benzene (103962-05-6) → 4-(trifluoromethoxy)benzonitrile (332-25-2)

Guidance literature:

With copper(II) orthophosphate; In N,N-dimethyl-formamide; at 120 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2020.152749

upstream raw materials:

4-cyanophenyl trichloromethyl ether

1-bromo-4-(trifluoromethoxy)benzene

1-naphthyl cyanate

copper(I) cyanide

Downstream raw materials:

4-trifluoromethoxybenzamide

4-trifluoromethoxybenzoic acid

4-trifluoromethoxyphenyl cyclopropyl ketone

cyclopropylmagnesium bromide

Refernces

• 1、 Chen, Qingqing,Han, Hongwei,Lin, Hongyan,Ma, Xiaopeng,Qi, Jinliang,Wang, Xiaoming,Yang, Yonghua,Zhou, Ziling. "One pot synthesis of aryl nitriles from aromatic aldehydes in a water environment". . p. 24232 - 24237. Retrieved 2021/07/29.
• 2、 Liu, Si-Zhan,Li, Jing,Xue, Cao-Gen,Xu, Xue-Tao,Lei, Lin-Sheng,Huo, Chen-Yu,Wang, Zhen,Wang, Shao-Hua. "Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile". supporting information. . Retrieved 2021/02/01.