347-37-5

Basic information

• Product Name: N-4-biphenylyl-2,2,2-trifluoroacetamide
• Synonyms: N-4-biphenylyl-2,2,2-trifluoroacetamide;N-(biphenyl-4-yl)-2,2,2-trifluoroacetamide
• CAS NO: 347-37-5
• Molecular Formula: C₁₄H₁₀F₃NO
• Molecular Weight: 265.2305096
• Mol File: 347-37-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 370.8°C at 760 mmHg
• Flash Point: 178.1°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: N-4-biphenylyl-2,2,2-trifluoroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-4-biphenylyl-2,2,2-trifluoroacetamide(347-37-5)
• EPA Substance Registry System: N-4-biphenylyl-2,2,2-trifluoroacetamide(347-37-5)

Safety Data

• Hazardous Substances Data: 347-37-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H10F3NO/c15-14(16,17)13(19)18-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,18,19)

Upstream product

• 92-67-1 4-phenylalanine 
• 407-25-0 trifluoroacetic anhydride 
• 24568-11-4 N-(4-bromophenyl)-2,2,2-trifluoro-acetamide 
• 98-80-6 phenylboronic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 71-43-2 benzene 
• 354-38-1 2,2,2-trifluoroacetamide 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 76-05-1 trifluoroacetic acid 
• 106-40-1 4-bromo-aniline 
• 622-37-7 Phenyl azide 

Downstream Products

• 1338468-85-1 C₂₁H₂₄N₂O₂ 
• 1291779-93-5 (1R,3S)-3-(6-dimethylamino-hexanoylamino)-cyclopentanecarboxylic acid N-biphenyl-4-yl-N-methyl-amide 
• 1291779-92-4 (1R,3S)-3-(3-ethyl-ureido)-cyclopentanecarboxylic acid N-biphenyl-4-yl-N-methyl-amide 
• 1291779-90-2 (1R,3S)-3-isobutyrylamino-cyclopentanecarboxylic acid N-biphenyl-4-yl-N-methyl-amide 
• 1291779-89-9 (1R,3S)-3-propionylamino-cyclopentanecarboxylic acid N-biphenyl-4-yl-N-methyl-amide 
• 1291779-91-3 (1R,3S)-3-acetylamino-cyclopentanecarboxylic acid N-biphenyl-4-yl-N-methyl-amide 
• 71151-89-8 1,1'-biphenyl-4-yl α,α,α-trifluoroacetate 

Relevant articles and documents

A simple and efficient method for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene

A simple and efficient one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene is reported. A mixed trifluoroacetic anhydride generated in situ reacts with a variety of arylamines to give the corresponding trifluroacetamides in high yields.

Discovery of BI 99179, a potent and selective inhibitor of type i fatty acid synthase with central exposure

Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats.

N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride

A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.