6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline

Base Information

• Chemical Name: 6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline
• CAS No.: 391860-73-4
• Molecular Formula: C₁₃H₉ClF₃N
• Molecular Weight: 271.669
• Hs Code.: 2933497050
• UNII: ZC619V1CML
• DSSTox Substance ID: DTXSID30192427
• Nikkaji Number: J1.856.813F
• Wikidata: Q27295300
• Mol file: 391860-73-4.mol

Synonyms:6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline;391860-73-4;UNII-ZC619V1CML;ZC619V1CML;6-Chloro-2-cyclopropyl-4-(trifluoromethyl)-quinoline;2-Cyclopropyl-6-chloro-4-(trifluoromethyl)quinoline;Quinoline, 6-chloro-2-cyclopropyl-4-(trifluoromethyl)-;6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline;Efavirenz Related Compound C (USP);Efavirenz Related Compound C;DTXSID30192427;CXGFIHCGWHSIQO-UHFFFAOYSA-N;MFCD26142873;SM-097;STL454185;EFAVIRENZ IMPURITY F [WHO-IP];SB71359;AS-74371;W18522;A899653;2-Cyclopropyl-4-(trifluoromethyl)-6-chloroquinoline;Q27295300

Chemical Property of 6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline

Chemical Property:

• Melting Point: 62.1-63.9℃
• Boiling Point: 337.8±37.0 °C(Predicted)
• PKA: 2.32±0.50(Predicted)
• PSA: 12.89000
• Density: 1.428±0.06 g/cm3(Predicted)
• LogP: 4.78440
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 271.0375615
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

98% ^*data from raw suppliers

6-Chloro-2-cyclopropyl-4-(trifluoromethyl)-quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=NC3=C(C=C(C=C3)Cl)C(=C2)C(F)(F)F
• Uses: 6-Chloro-2-cyclopropyl-4-(trifluoromethyl)-quinoline is an impurity of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor and antiviral agent.

Technology Process of 6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline

There total 14 articles about 6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 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: 97.0%

Cyclopropyl methyl ketone (765-43-5) + 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) → 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline (391860-73-4)

Guidance literature:

With L-proline potassium salt; In dimethyl sulfoxide; at 20 ℃; for 18h; regioselective reaction;

DOI:10.1016/j.tet.2013.06.017

Reference yield: 89.0%

(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) → 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline (391860-73-4)

Guidance literature:

With triethylsilane; zinc(II) iodide; In 1,2-dichloro-ethane; at 20 ℃; for 24h;

DOI:10.1055/s-0028-1083627

Reference yield: 85.0%

1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone hydrochloride (173676-59-0) + Cyclopropylacetylene (6746-94-7) → 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline (391860-73-4)

Guidance literature:

With silver fluoride; triethylamine; triphenylphosphine; In water; at 120 ℃; Sealed tube;

DOI:10.1039/c3ra41991f

upstream raw materials:

chlorobenzene

(2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol

Cyclopropylacetylene

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

Refernces

• 1、 -. "Synthesis method of efavirenz quinoline impurities". Paragraph 0029; 0031; 0034; 0035. . Retrieved 2018/01/09.
• 2、 Cheng, Jie,Zhai, Hong,Bai, Jun,Tang, Jun,Lv, Ling,Sun, Bei. "Electrophile-driven copper-catalyzed one-pot synthesis of 3-halogen quinoline derivatives". . p. 4044 - 4046. Retrieved 2015/02/02.