2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide

Base Information

• Chemical Name: 2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide
• CAS No.: 1939-19-1
• Molecular Formula: C12H14 F3 N O
• Molecular Weight: 245.244
• Hs Code.: 2924299090
• European Community (EC) Number: 659-336-7
• DSSTox Substance ID: DTXSID10351934
• Nikkaji Number: J3.551.765K
• Wikidata: Q82128778
• Mol file: 1939-19-1.mol

Synonyms:1939-19-1;2,2-dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide;N-(2,2-Dimethylpropanoyl)-3-(trifluoromethyl)aniline;N-(3-(trifluoromethyl)phenyl)pivalamide;3-(Trifluoromethyl)pivalanilide;Propanamide,2,2-dimethyl-N-[3-(trifluoromethyl)phenyl]-;2,2-Dimethyl-N-[3-(trifluoromethyl)phenyl]-propanamide;Maybridge1_007803;SCHEMBL4455493;HMS563K15;DTXSID10351934;3-trifluoromethyl-n-pivaloylaniline;MFCD00095901;AKOS003865674;AC-14428;FT-0633925;2,2-Dimethyl-3'-Trifluoromethyl-Propionanilide

Chemical Property of 2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide

Chemical Property:

• Vapor Pressure: 0.000286mmHg at 25°C
• Melting Point: 107 °C
• Refractive Index: 1.489
• Boiling Point: 322.1°Cat760mmHg
• PKA: 14.58±0.70(Predicted)
• Flash Point: 148.6°C
• PSA: 29.10000
• Density: 1.192g/cm³
• LogP: 3.76300
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 245.10274856
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C(=O)NC1=CC=CC(=C1)C(F)(F)F
• Uses: Intermediate for the preparation of Flunixin and other derivatives of this analgesic.

Technology Process of 2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide

There total 6 articles about 2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide 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%

pivaloyl chloride (3282-30-2) + 3-trifluoromethylaniline (98-16-8) → N-(3-(trifluoromethyl)phenyl)pivalamide (1939-19-1)

Guidance literature:

With triethylamine;

Reference yield: 85.0%

N-t-butyl-N'-[3-(trifluoromethyl)phenyl]-S-phenylisothiourea + Trimethylacetic acid (75-98-9) → N-(3-(trifluoromethyl)phenyl)pivalamide (1939-19-1)

Guidance literature:

With iron(III)-acetylacetonate; In isopropyl alcohol; at 83 ℃; for 24h; Microwave irradiation;

DOI:10.1021/acs.orglett.6b02247

Reference yield: 65.0%

Togni's reagent II (887144-94-7) + N-pivaloylaniline (6625-74-7) → N-(3-(trifluoromethyl)phenyl)pivalamide (1939-19-1) + 2,2-dimethyl-N-(4-trifluoromethylphenyl)propanamide (25617-34-9) + N-<2-(trifluromethyl)phenyl>-2,2-dimethylpropanamide (125686-52-4)

Guidance literature:

With copper(l) chloride; In tert-butyl alcohol; at 30 ℃; for 24h; Solvent; Temperature; Time; regioselective reaction; Catalytic behavior; Inert atmosphere; Sealed tube;

DOI:10.1039/c3cc41331d

upstream raw materials:

pivaloyl chloride

3-trifluoromethylaniline

aniline

Togni's reagent II

Downstream raw materials:

2,2-dimethyl-1-[2-(3-trifluoromethylphenylamino)phenyl]propan-1-one

N-[2-(α-hydroxyethyl)-3-trifluoromethylphenyl]-2,2-dimethylpropionamide

flunixin

ethyl 2-(2-methyl-3-trifluoromethylanilino)nicotinate

Refernces

• 1、 Wang, Dongjie,Xu, Xu,Zhang, Jingyu,Zhao, Yingsheng. "Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst". . p. 2696 - 2705. Retrieved 2021/02/27.
• 2、 Zhu, Yan-Ping,Sergeyev, Sergey,Franck, Philippe,Orru, Romano V. A.,Maes, Bert U. W.. "Amine Activation: Synthesis of N-(Hetero)arylamides from Isothioureas and Carboxylic Acids". supporting information. p. 4602 - 4605. Retrieved 2016/09/28.