209414-27-7

Basic information

• Product Name: (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol
• Synonyms: BenzeneMethanol,2-aMino-5-chloro-a-(2-cyclopropylethynyl)-a-(trifluoroMethyl)-, (aS)-;(S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol (E05);(2R)-2-(2-Amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol;(R)-2-(2-Amino-5-chloro-phenyl)-4-cyclopropyl-1,1,1-trifluoro-but-3-yn-2-ol;(S)-5-Chloro-Alpha-(Cyclopropylethynyl)-2-Amino-Alpha-(Trifluoromethyl)-Benzenemethanol;(S)-1-(2-AMINO-5-CHLOROPHENYL)-1-(TRIFLUOROMETHYL)-3-CYCLOPROPYL-2-PROPYN-1-OL;(S)-5-CHLORO-A-(CYCLOPROPYLETHYNYL)-2-AMINO-A-(TRIFLUOROMETHYL)BENZENE METHANOL;Efavirenz Related Compound A (20 mg) ((S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol)
• CAS NO: 209414-27-7
• Molecular Formula: C₁₃H₁₁ClF₃NO
• Molecular Weight: 289.68
• Mol File: 209414-27-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 425.052 °C at 760 mmHg
• Flash Point: 210.864 °C
• Appearance: /
• Density: 1.46
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.13±0.24(Predicted)
• CAS DataBase Reference: (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol(209414-27-7)
• EPA Substance Registry System: (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol(209414-27-7)

Safety Data

• Hazardous Substances Data: 209414-27-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the preparation of Efavirenz (E425000) 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-/m0/s1

Upstream product

• 6746-94-7 Cyclopropylacetylene 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 
• 201218-07-7 tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 
• 106-47-8 4-chloro-aniline 
• 201218-10-2 4-cyclopropyl-1,1,1-trifluoro-but-3-yn-2-one 
• 56571-91-6 (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 195372-65-7 N-(2-bromo-4-chlorophenyl)pivalamide 
• 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 

Downstream Products

• 154598-52-4 efavirenz 
• 154801-74-8 (R)-efavirenz 
• 391860-73-4 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 220978-05-2 (S)-2-[1-hydroxy-1-trifluoromethyl-3-cyclopropylpropyn-2-yl]-4-chloroaniline hydrobromide 
• 220978-02-9 (S)-5-chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol hydrocloride 
• 211563-41-6 C₁₆H₁₅ClF₃NO₃ 
• 211563-40-5 [4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid methyl ester 
• 211563-39-2 [4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid 4-nitro-phenyl ester 
• 1236354-27-0 (S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol methanesulfonate 
• 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.

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).

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.