(S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-OL

Base Information

• Chemical Name: (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-OL
• CAS No.: 209414-27-7
• Molecular Formula: C13H11ClF3NO
• Molecular Weight: 289.685
• Hs Code.: 2922199695
• European Community (EC) Number: 606-673-2
• UNII: Z3E01963ZY
• DSSTox Substance ID: DTXSID30175119
• Nikkaji Number: J1.067.505G
• Wikidata: Q27294946
• ChEMBL ID: CHEMBL3344471
• Mol file: 209414-27-7.mol

Synonyms:209414-27-7;(S)-1-(2-AMINO-5-CHLOROPHENYL)-1-(TRIFLUOROMETHYL)-3-CYCLOPROPYL-2-PROPYN-1-OL;(S)-2-(2-AMINO-5-CHLOROPHENYL)-4-CYCLOPROPYL-1,1,1-TRIFLUOROBUT-3-YN-2-OL;Efavirenz aminoalcohol;154598-58-0;(2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol;(S)-2-(2-Amino-5-chloro-phenyl)-4-cyclopropyl-1,1,1-trifluoro-but-3-yn-2-ol;Z3E01963ZY;EFAVIRENZ IMPURITY E;SCHEMBL524307;UNII-Z3E01963ZY;CHEMBL3344471;DTXSID30175119;(-)-EFAVIRENZ AMINOALCOHOL;BCP28777;MFCD09751012;SD-573;1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol;AKOS016003800;CS-T-02294;SB35277;(S)-5-Chloro-alpha-(cyclopropylethynyl)-2-amino-alpha-(trifluoromethyl)benzenemethanol;AS-10054;CS-0341179;EFAVIRENZ AMINOALCOHOL [USP IMPURITY];E80376;A815040;EFAVIRENZ IMPURITY, EFAVIRENZ AMINOALCOHOLA-;J-502340;Q27294946;(S)-1,1,1-Trifluoro-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-3-butyne-2-ol;(S)-2-(2-AMINO-5-CHLOROPHENYL)-4-CYCLOPROPYL-1,1,1-TRIFLUORO-3-BUTYN-2-OL;(S)-4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl) aniline;(S)-4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)aniline;(S)-5-Chloro-alpha-(cyclopropylethynyl)-2-amino-alpha-(trifluoromethyl) benzenemethanol;(S)-5-Chloro-alpha-(cyclopropylethynyl)-2-amino-alpha-(trifluoromethyl)-benzenemethanol;(s)-5-chloro-alpha-(cyclopropylethynyl)-2-amino-alpha-(trifluoromethyl)benzene methanol;(.ALPHA.S)-2-AMINO-5-CHLORO-.ALPHA.-(CYCLOPROPYLETHYNYL)-.ALPHA.-(TRIFLUOROMETHYL)BENZENEMETHANOL;BENZENEMETHANOL, 2-AMINO-5-CHLORO-.ALPHA.-(2-CYCLOPROPYLETHYNYL)-.ALPHA.-(TRIFLUOROMETHYL)-, (.ALPHA.S)-

Chemical Property of (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-OL

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.575
• Boiling Point: 425.052 °C at 760 mmHg
• PKA: 9.13±0.24(Predicted)
• Flash Point: 210.864 °C
• PSA: 46.25000
• Density: 1.462 g/cm³
• LogP: 3.66670
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 289.0481262
• Heavy Atom Count: 19
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C#CC(C2=C(C=CC(=C2)Cl)N)(C(F)(F)F)O
• Isomeric SMILES: C1CC1C#C[C@](C2=C(C=CC(=C2)Cl)N)(C(F)(F)F)O
• Uses: Intermediate in the preparation of Efavirenz (E425000) impurity.

Technology Process of (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-OL

There total 33 articles about (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-OL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Cyclopropylacetylene (6746-94-7) + 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) → (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol (209414-27-7,927812-33-7,154598-58-0)

Guidance literature:

With (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc(II); In toluene; for 1h;

With methanol; In toluene; for 0.5h;

Cyclopropylacetylene; 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone; With butyl magnesium bromide; more than 3 stages; Product distribution / selectivity;

Reference yield: 96.0%

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) + cyclopropylacetylene magnesium chloride (216006-64-3) → (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol (209414-27-7,927812-33-7,154598-58-0)

Guidance literature:

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone; cyclopropylacetylene magnesium chloride; With methanol; (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc(II); In toluene; at 20 ℃; for 9h;

With citric acid; In water; toluene; Product distribution / selectivity;

Reference yield: 95.0%

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) + cyclopropyl acetylenyllithium (201218-09-9) → (αR)-2-amino-5-chloro-α-(2-cyclopropylethynyl)-α-(trifluoromethyl)benzenemethanol (927812-33-7,154598-58-0) + (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol (209414-27-7,927812-33-7,154598-58-0)

Guidance literature:

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone; cyclopropyl acetylenyllithium; With methanol; (+/-)-erythro-2-dibenzylamino-1-phenyl-propanol-⁽¹⁾; dimethyl zinc(II); In toluene; for 9h;

With citric acid; In water; toluene; Product distribution / selectivity;

upstream raw materials:

Cyclopropylacetylene

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone

(S)-6-chloro-4-(cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine

cyclopropyl acetylenyllithium

Downstream raw materials:

efavirenz

(S)-5-chloro-α-(cyclopropylethynyl)-2-amino-α-(trifluoromethyl) benzenemethanol hydrocloride

(S)-2-[1-hydroxy-1-trifluoromethyl-3-cyclopropylpropyn-2-yl]-4-chloroaniline hydrobromide

(R)-efavirenz

Refernces

• 1、 -. "Efavirenz synthesis method and method for preparing intermediate of efavirenz". Paragraph 0041-0046. . Retrieved 2020/09/02.
• 2、 -. "Synthetic method of efavirenz key intermediate". Paragraph 0021. . Retrieved 2019/01/08.