1181455-55-9

Basic information

• Product Name: 5-(trifluoromethyl)-2-(phenylethynyl)aniline
• Synonyms: 5-(trifluoromethyl)-2-(phenylethynyl)aniline
• CAS NO: 1181455-55-9
• Molecular Weight: 261.246
• Mol File: 1181455-55-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 5-(trifluoromethyl)-2-(phenylethynyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(trifluoromethyl)-2-(phenylethynyl)aniline(1181455-55-9)
• EPA Substance Registry System: 5-(trifluoromethyl)-2-(phenylethynyl)aniline(1181455-55-9)

Safety Data

• Hazardous Substances Data: 1181455-55-9(Hazardous Substances Data)

Upstream product

• 454-79-5 2-Bromo-5-trifluoromethylaniline 
• 536-74-3 phenylacetylene 
• 105202-02-6 2-iodo-4-(trifluoromethyl)benzenamine 
• 1314806-96-6 2-bromo-1-(phenylethynyl)-4-(trifluoromethyl)benzene 

Downstream Products

• 1380395-16-3 N-benzyl-2-(phenylethynyl)-5-(trifluoromethyl)aniline 
• 1380395-27-6 methyl 1-benzyl-2-phenyl-6-(trifluoromethyl)-1H-indole-3-carboxylate 
• 1264617-09-5 1-[methoxy(phenyl)methyl]-2-phenyl-6-trifluoromethylindole-3-carboxylic acid methyl ester 

Relevant articles and documents

The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators

The first generation of CB1 positive allosteric modulators (e.g., ZCZ011) featured a 3-nitroalkyl-2-phenyl-indole structure. Although a small number of drugs include the nitro group, it is generally not regarded as being "drug-like", and this is particularly true for aliphatic nitro groups. There are very few case studies where an appropriate bioisostere replaced a nitro group that had a direct role in binding. This may be indicative of the difficulty of replicating its binding interactions. Herein, we report the design and synthesis of ligands targeting the allosteric binding site on the CB1 cannabinoid receptor, in which a CF3 group successfully replaced the aliphatic NO2. In general, the CF3-bearing compounds were more potent than their NO2 equivalents and also showed improved in vitro metabolic stability. The CF3 analogue (1) with the best balance of properties was selected for further pharmacological evaluation. Pilot in vivo studies showed that (±)-1 has similar activity to (±)-ZCZ011, with both showing promising efficacy in a mouse model of neuropathic pain.

A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines

A Pd(ii)-Ag(i) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one-pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2-iodoanilines.

CANNABINOID TYPE 1 RECEPTOR MODULATORS

The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparatio