927812-33-7

Basic information

• Product Name: (R)-5-Chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol
• Synonyms: (aR)-2-amino-5-chloro-α-(2-cyclopropylethynyl)-α-(trifluoromethyl)benzenemethanol;(R)-5-Chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol;(aR)-2-amino-5-chloro-a-(2-cyclopropylethynyl)-a-(trifluoromethyl)benzenemethanol;(R)-5-Chloro-a-(cyclopropylethynyl)-2-amino-a-(trifluoromethyl) benzenemethanol;(R)-5-Chloro-alpha-(cyclopropylethynyl)-2-amino-alpha-(trifluoromethyl)benzenemethanol;(αR)-2-AMino-5-chloro-α-(2-cyclopropylethynyl)-α-(trifluoroMethyl)benzeneMethanol
• CAS NO: 927812-33-7
• Molecular Formula: C13H11ClF3NO
• Molecular Weight: 289.6807496
• Product Categories: Chiral Reagents;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 927812-33-7.mol
• Article Data: 42

Chemical Properties

• Melting Point: 133-135°C
• Boiling Point: 425.1 °C at 760 mmHg
• Flash Point: 210.9 °C
• Appearance: /
• Density: 1.46 g/cm³
• Vapor Pressure: 5.54E-08mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (R)-5-Chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-Chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol(927812-33-7)
• EPA Substance Registry System: (R)-5-Chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol(927812-33-7)

Safety Data

• Hazardous Substances Data: 927812-33-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 927812-33-7 differently. You can refer to the following data:
1. Efavirenz (E425000) impurity.
2. Efavirenz impurity

InChI:InChI=1/C13H11ClF3NO/c14-9-3-4-11(18)10(7-9)12(19,13(15,16)17)6-5-8-1-2-8/h3-4,7-8,19H,1-2,18H2/t12-/m1/s1

Upstream product

• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 201218-09-9 cyclopropyl acetylenyllithium 
• 220961-15-9 iodomagnesium cyclopropylacetylide 
• 216006-64-3 cyclopropylacetylene magnesium chloride 
• 6746-94-7 Cyclopropylacetylene 
• 209414-26-6 (S)-6-chloro-4-(cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine 
• 925-90-6 ethylmagnesium bromide 
• 181190-33-0 N-(4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)pivalamide 
• 106-47-8 4-chloro-aniline 
• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 
• 209460-09-3 1-[5-chloro-2-(tritylamino)phenyl]-2,2,2-trifluoroethan-1-one 
• 221177-50-0 2-[5-chloro-2-(trityloamino)phenyl]-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 
• 201218-07-7 tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 

Downstream Products

• 1453095-83-4 3-bromo-6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 391860-73-4 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 1453095-77-6 3,6-dichloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 177530-94-8 (S)-N-(4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)pivalamide 

Relevant articles and documents

Method for asymmetric synthesis of anti-Aids drug, namely efavirenz key intermediate

The invention discloses a method for asymmetric synthesis of an anti-Aids drug, namely an efavirenz key intermediate. The method comprises the following steps that in an organic solvent, fluoride, anorganic ligand (9S)-6'-methoxy-deoxidized cinchonine-9-ol and cyclopropyl acetylene are evenly stirred, an organic zinc solution is slowly added at the temperature of 15-25 DEG C, after constant-temperature stirring is conducted for 3-5 hours, tetraisopropyl titanate is added, stirring is continued to be conducted for 2-3 hours, then the temperature is decreased to minus 20 DEG C to 0 DEG C, 5-chloro-2-amino-trifluorobenzophenone is added, a mixture is stirred at the temperature of minus 20 DEG C to 0 DEG C for 5-12 hours, after a reaction is completed, a proton source is added for a quenchingreaction, then a certain amount of activated carbon is added, a mixture is stirred for 0.5 hour and filtered, an organic phase and a water phase are separated in an extraction mode, the organic phaseis washed, dried and subjected to vacuum concentration, and after purification, the efavirenz key intermediate is obtained. The technological process is short, the technological condition is mild, operation is easy, environmental protection is achieved, the cost is low, and the method is suitable for industrial production.

Synthetic method of efavirenz key intermediate

The invention provides a synthetic method of an efavirenz key intermediate. The synthetic method comprises the following steps: carrying out reaction on parachloroaniline and pivaloyl chloride to protect amino to obtain N-(4-chlorphenyl)-2,2-dimethyl propanamide; carrying out Friedel-Crafts acylation reaction on the product and Friedel-Crafts acylation under action of aluminum trichloride to hydrolyze to obtain 4-chloro-2-trifluoroacetyl aniline hydrochloride in an acidic condition; and then carrying out alkalization to obtain 4-chloro-2-trifluoroacetyl aniline, carrying out reaction with cyclopropyl acetylene magnesium chloride in a catalytic system formed by a ligand (1R, 2S)-1-phenyl-2-(1-pyrrolidyl)-1-propyl alcohol, and carrying out an asymmetrical self-catalytic reaction to obtain the efavirenz key intermediate. The synthetic method of the efavirenz key intermediate, provided by the invention, is cheap and easily available in raw material, low in toxicity of reagent and mild in reaction condition, amino protection and deprotection are not carried out frequently, the line is concise, the yields of reaction of each step are excellent, and the total yield is high.

Catalytic Enantioselective Synthesis of Key Propargylic Alcohol Intermediates of the Anti-HIV Drug Efavirenz

The catalytic, enantioselective synthesis of key propargylic alcohol intermediates toward the synthesis of the anti-HIV drug efavirenz is reported. Using a recently reported chiral-at-ruthenium catalyst (J. Am. Chem. Soc. 2017, 139, 4322), catalytic enantioselective alkynylations of 1-(2,5-dichlorophenyl)-2,2,2-trifluoroethanone (99% yield, 95% ee) and 1-(5-chloro-2-nitrophenyl)-2,2,2-trifluoroethanone (97% yield, 99% ee) are achieved using catalyst loadings of merely 0.2 mol % (ca. 500 TON).