6-Bromo-2-trifluoromethylquinoline

Base Information

• Chemical Name: 6-Bromo-2-trifluoromethylquinoline
• CAS No.: 176722-64-8
• Molecular Formula: C₁₀H₅BrF₃N
• Molecular Weight: 276.056
• DSSTox Substance ID: DTXSID20571525
• Wikidata: Q82459620
• Mol file: 176722-64-8.mol

Synonyms:6-Bromo-2-trifluoromethylquinoline;176722-64-8;6-BROMO-2-(TRIFLUOROMETHYL)QUINOLINE;QUINOLINE, 6-BROMO-2-(TRIFLUOROMETHYL)-;MFCD08166328;Quinoline,6-bromo-2-(trifluoromethyl)-;SCHEMBL2117037;DTXSID20571525;KSGBXTJLAABRJI-UHFFFAOYSA-N;AKOS000320171;AB43561;DS-0506;SY107768;CS-0018972;A812206;J-518348;6-bromo-2-(trifluoromethyl)quinoline

Chemical Property of 6-Bromo-2-trifluoromethylquinoline

Chemical Property:

• Vapor Pressure: 0.00515mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 284.3°Cat760mmHg
• Flash Point: 125.7°C
• PSA: 12.89000
• Density: 1.658g/cm³
• LogP: 4.01610
• Storage Temp.: 2-8°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 274.95575
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

98%min ^*data from raw suppliers

6-Bromo-2-trifluoromethylquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=N2)C(F)(F)F)C=C1Br

Technology Process of 6-Bromo-2-trifluoromethylquinoline

There total 5 articles about 6-Bromo-2-trifluoromethylquinoline 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: 77.0%

2-azido-5-bromobenzaldehyde (1001621-59-5) + 1,1,1-trifluoro-2-propanone (421-50-1) → 6-bromo-2-(trifluoromethyl)quinoline (176722-64-8)

Guidance literature:

With triphenylphosphine; lithium hydroxide; In acetonitrile; at 95 ℃; for 6h;

DOI:10.1039/c8gc03180k

Reference yield: 62.0%

6-bromoquinoline (5332-25-2) + (trifluoromethyl)trimethylsilane (81290-20-2) → 6-bromo-2-(trifluoromethyl)quinoline (176722-64-8)

Guidance literature:

6-bromoquinoline; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydrogen difluoride; In 1,4-dioxane; at 25 ℃; for 0.00833333h;

(trifluoromethyl)trimethylsilane; With trifluoroacetic acid; In 1,4-dioxane; at 25 ℃; for 24h;

With [bis(acetoxy)iodo]benzene; In 1,4-dioxane; at 25 ℃; for 2h;

DOI:10.1021/acs.orglett.8b00339

Reference yield: 40.0%

(2,2’-bipyridine)Zn(CF3)2 + 6-bromo-1-(4-methoxybenzyl)quinolin-1-ium bromide → 6-bromo-2-(trifluoromethyl)quinoline (176722-64-8)

Guidance literature:

(2,2’-bipyridine)Zn(CF₃)₂; 6-bromo-1-(4-methoxybenzyl)quinolin-1-ium bromide; In dimethyl sulfoxide; at 60 ℃; for 12h; Inert atmosphere; Sealed tube;

With ammonium cerium (IV) nitrate; In methanol; water; at 25 ℃; for 24h;

DOI:10.1016/j.tet.2021.132477

upstream raw materials:

6-bromoquinoline

(trifluoromethyl)trimethylsilane

2-azido-5-bromobenzaldehyde

1,1,1-trifluoro-2-propanone

Refernces

• 1、 Zhang, Xiaofeng,Ma, Xiaoming,Qiu, Weiqi,Evans, Jason,Zhang, Wei. "Cascade Knoevenagel and aza-Wittig reactions for the synthesis of substituted quinolines and quinolin-4-ols". supporting information. p. 349 - 354. Retrieved 2019/01/28.
• 2、 Keller,Schlosser. "2-(trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization". . p. 4637 - 4644. Retrieved 2007/10/03.