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

• 6746-94-7 Cyclopropylacetylene 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 925-90-6 ethylmagnesium bromide 
• 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 
• 201218-09-9 cyclopropyl acetylenyllithium 
• 56571-91-6 (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 1352784-90-7 (S)-1-(5-chloro-2-nitrophenyl)-1-trifluoromethyl-3-cyclopropyl-2-propyn-1-ol 
• 1352784-89-4 1-(5-chloro-2-nitrophenyl)-3-cyclopropylprop-2-yn-1-one 
• 1352784-88-3 1-(5-chloro-2-nitrophenyl)-3-cyclopropylprop-2-yn-1-ol 
• 14267-92-6 1-chloro-4-pentyne 
• 220961-15-9 iodomagnesium cyclopropylacetylide 
• 216006-64-3 cyclopropylacetylene magnesium chloride 

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

Efavirenz synthesis method and method for preparing intermediate of efavirenz

The invention discloses an efavirenz synthesis method and a method for preparing an intermediate of efavirenz. The efavirenz synthesis method comprises the following steps: mixing (2S)-2-(2-amino-5-chlorphenyl)-4-cyclopropyl-1, 1, 1-trifluoromethyl-3-butyne-2-ol, methyl tert-butyl ether and a potassium bicarbonate aqueous solution; adding a triphosgene-containing benzene or triphosgene-containingisopropyl ether solution, and reacting until the raw materials disappear; separating liquid, and washing with edible salt water; drying and concentrating the organic phase to obtain a crude product efavirenz; and recrystallizing to obtain the efavirenz. The yield of the product is improved, so that the cost is greatly reduced, and the market competitiveness is improved.

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.

METHOD FOR THE MANUFACTURE OF EFAVIRENZ

This invention relates to a method for the manufacture of optically pure (S)-6- chloro-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1 -benzoxazin- 2-one. Specifically, this invention relates to a flow synthesis method for the manufacture of (S)-6-chloro-(cyclopropylethynyl)-1,4-dihydro-4- (trifluoromethyl)-2H-3,1 -benzoxazin-2-one.