391860-73-4

Basic information

• Product Name: Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline)
• Synonyms: Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline);Efavirenz Related CoMpound C;2-Cyclopropyl-6-chloro-4-(trifluoromethyl)quinoline;SM 097;Efavirenz Quinoline Analog Impurity
• CAS NO: 391860-73-4
• Molecular Formula: C13H9ClF3N
• Molecular Weight: 271.6654696
• Product Categories: Anti-virals, Inhibitors, Non-nucleoside Reverse Transcriptase, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 391860-73-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 62.1-63.9℃
• Boiling Point: 337.8±37.0 °C(Predicted)
• Appearance: /
• Density: 1.428±0.06 g/cm3(Predicted)
• PKA: 2.32±0.50(Predicted)
• CAS DataBase Reference: Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline)(CAS DataBase Reference)
• NIST Chemistry Reference: Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline)(391860-73-4)
• EPA Substance Registry System: Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline)(391860-73-4)

Safety Data

• Hazardous Substances Data: 391860-73-4(Hazardous Substances Data)

Usage

Uses

6-Chloro-2-cyclopropyl-4-(trifluoromethyl)-quinoline is an impurity of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor and antiviral agent.

Upstream product

• 6746-94-7 Cyclopropylacetylene 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 168834-43-3 6-amino-3-chloro-α-cyclopropylethynyl-α-(trifluoromethyl)benzyl alcohol 
• 173676-59-0 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone hydrochloride 
• 209414-27-7 (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 
• 765-43-5 Cyclopropyl methyl ketone 
• 209414-26-6 (S)-6-chloro-4-(cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine 
• 108-90-7 chlorobenzene 

Relevant articles and documents

NHC-Cu(I)-Catalyzed Friedl?nder-Type Annulation of Fluorinated o-Aminophenones with Alkynes on Water: Competitive Base-Catalyzed Dibenzo[b,f][1,5]diazocine Formation

An efficient, easily scalable synthesis of 4-trifluoromethylquinolines and naphthydrines (as well as their difluoro- and perfluoro-analogues) as a result of tandem direct catalytic alkynylation/dehydrative condensation of o-aminofluoromethylketones (o-FMKs), for the first time catalyzed by NHC-copper(I) complexes on water, is reported. A wide range of terminal alkynes is tolerated under the reaction conditions, including β-lactam-, steroid-, and sugar-derived ones, leading to desired quinolines and naphthydrines with good yields. Further investigations proved that o-FMKs could be efficiently transformed into a rare class of heterocyclic compounds - dibenzo[b,f][1,5]diazocines - by a base-catalyzed condensation, also on water. The developed method was applied for gram-scale synthesis of a fluorinated analogue of G protein-coupled receptor antagonist (GPR91).

Electrophile-driven copper-catalyzed one-pot synthesis of 3-halogen quinoline derivatives

A convenient and regioselective one-pot synthesis of 3-chloride or 3-bromide quinoline derivatives was achieved through a Grignard addition reaction by alkynyl Grignard regent to o-trifluoroacetyl aniline and a Cu(II)-catalyzed cyclization-halogenation tandem reaction with aqueous HCl or HBr as electrophilic reagent.

Proline potassium salt: A superior catalyst to synthesize 4-trifluoromethyl quinoline derivatives via Friedlander annulation

Proline potassium salt was successfully firstly used to catalyze the Friedlander annulation toward the synthesis of 4-trifluoromethyl-substituted quinolines from the substituted 2-trifluoroacetyl anilines and variety carbonyl compounds under mild conditions in good to excellent yields. This catalyst provides several advantages, such as shorter reaction time, high regioselectivity, functional group tolerance, and broad substrate scope.