3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile

Base Information

• Chemical Name: 3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile
• CAS No.: 122454-46-0
• Molecular Formula: C10H6F3NO2
• Molecular Weight: 229.158
• Hs Code.: 2926909090
• European Community (EC) Number: 671-711-7
• DSSTox Substance ID: DTXSID90380429
• Wikidata: Q82170659
• Mol file: 122454-46-0.mol

Synonyms:122454-46-0;3-oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile;4-(Trifluoromethoxy)Benzoyl Acetonitrile;3-Oxo-3-(4-(trifluoromethoxy)phenyl)propanenitrile;(4-trifluoromethoxybenzoyl)acetonitrile;4-(trifluoromethoxy)benzoylacetonitrile;3-Oxo-3-[4-(trifluoromethoxy)phenyl]propionitrile;Benzenepropanenitrile, beta-oxo-4-(trifluoromethoxy)-;Maybridge1_004897;SCHEMBL136576;HMS555G13;DTXSID90380429;MFCD00052146;AKOS007930756;BH-0416;CS-0081145;FT-0616884;C77813;A804896;Benzenepropanenitrile,b-oxo-4-(trifluoromethoxy)-;W-205149;3-oxidanylidene-3-[4-(trifluoromethyloxy)phenyl]propanenitrile

Chemical Property of 3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile

Chemical Property:

• Melting Point: 82-84 °C
• Boiling Point: 315.4 °C at 760 mmHg
• Flash Point: 144.6 °C
• PSA: 50.09000
• Density: 1.338 g/cm³
• LogP: 2.68158
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 229.03506292
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile

There total 3 articles about 3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile 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: 88.0%

malononitrile (109-77-3) + 4-trifluoromethoxyphenylboronic acid (139301-27-2) → 3-oxo-3-(4-(trifluoromethoxy)phenyl)propanenitrile (122454-46-0)

Guidance literature:

With 4,4'-dimethyl-2,2'-bipyridines; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In water; toluene; at 80 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.joc.0c02388

Reference yield: 85.0%

sodium cyanide (143-33-9,25596-52-5) + 2-bromo-1-(4-(trifluoromethoxy)phenyl)ethanone (103962-10-3) → 3-oxo-3-(4-(trifluoromethoxy)phenyl)propanenitrile (122454-46-0)

Guidance literature:

In methanol; water; at 20 ℃; for 3h;

DOI:10.1071/CH03010

Reference yield: 64.0%

4-trifluoromethoxy-benzoic acid ethyl ester (587-18-8) + acetonitrile (75-05-8,26809-02-9) → 3-oxo-3-(4-(trifluoromethoxy)phenyl)propanenitrile (122454-46-0)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

4-trifluoromethoxy-benzoic acid ethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1039/c9cc07204g

upstream raw materials:

sodium cyanide

2-bromo-1-(4-(trifluoromethoxy)phenyl)ethanone

4-trifluoromethoxy-benzoic acid ethyl ester

acetonitrile

Downstream raw materials:

(2-amino-5-ethyl-thiophen-3-yl)-(4-trifluoromethoxy-phenyl)-methanone

C₁₆H₇F₄N₃O₃

C₁₇H₇F₆N₃O₃

Refernces

• 1、 Xu, Kai,Liu, Hao,Hou, Yilin,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin. "A Pd-catalyzed asymmetric allylic substitution cascade: Via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans". supporting information. p. 13295 - 13298. Retrieved 2019/11/13.