6-Bromo-4-hydroxy-2-(trifluoromethyl)quinoline

Base Information

• Chemical Name: 6-Bromo-4-hydroxy-2-(trifluoromethyl)quinoline
• CAS No.: 1701-22-0
• Molecular Formula: C₁₀H₅BrF₃NO
• Molecular Weight: 292.055
• Hs Code.: 2933499090
• NSC Number: 128778
• DSSTox Substance ID: DTXSID201275296
• Mol file: 1701-22-0.mol

Synonyms:1701-22-0;6-Bromo-4-hydroxy-2-(trifluoromethyl)quinoline;6-bromo-2-(trifluoromethyl)quinolin-4-ol;6-bromo-2-(trifluoromethyl)-1H-quinolin-4-one;6-BROMO-2-(TRIFLUOROMETHYL)QUINOLIN-4(1H)-ONE;500562-58-3;4-Quinolinol, 6-bromo-2-(trifluoromethyl)-;MFCD00153078;6-Bromo-2-trifluoromethyl-quinolin-4-ol;NSC128778;Maybridge3_004065;6-BROMO-2-(TRIFLUOROMETHYL)-4-QUINOLINOL;SCHEMBL4214227;2-(2-Nitrophenoxy)propanoicacid;DTXSID201275296;HMS1442I17;AKOS005203142;AKOS009159389;AC-7371;NSC-128778;SB69399;SB71554;IDI1_015452;AS-31287;SY005933;CS-0084827;FT-0620989;6-bromo-4-hydroxy-2-trifluoromethyl-quinoline;6-bromanyl-2-(trifluoromethyl)-1H-quinolin-4-one;A811168;6-Bromo-4-hydroxy-2-trifluoromethylquinoline, AldrichCPR

Chemical Property of 6-Bromo-4-hydroxy-2-(trifluoromethyl)quinoline

Chemical Property:

• Vapor Pressure: 0.0728mmHg at 25°C
• Melting Point: >290 °C
• Refractive Index: 1.554
• Boiling Point: 277.879 °C at 760 mmHg
• PKA: 6.16±0.40(Predicted)
• Flash Point: 121.857 °C
• PSA: 33.12000
• Density: 1.725 g/cm³
• LogP: 3.72170
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 290.95066
• Heavy Atom Count: 16
• Complexity: 339

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-bromo-2-(trifluoromethyl)quinolin-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45

MSDS Files:

Useful:

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

Technology Process of 6-Bromo-4-hydroxy-2-(trifluoromethyl)quinoline

There total 2 articles about 6-Bromo-4-hydroxy-2-(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:

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + 4-bromo-aniline (106-40-1) → 6-bromo-2-(trifluoromethyl)quinolin-4-ol (1701-22-0)

Guidance literature:

ethyl 4,4,4-trifluoroacetoacetate; 4-bromo-aniline; With magnesium sulfate; acetic acid; In ethanol; at 90 ℃; for 16h;

With dowtherm A; at 230 - 250 ℃; for 0.5h;

DOI:10.1021/acs.jafc.9b04224

Reference yield:

→ 6-bromo-2-(trifluoromethyl)quinolin-4-ol (1701-22-0)

Guidance literature:

4,4,4-Trifluor-acetessigsaeure-ethylester 1. Polyphosphorsaeure, 100grad 2. 4-Bromanilin, 140-150grad, 1.5 h 3. 20grad, 12 h;

Reference yield:

6-bromo-2-(trifluoromethyl)quinolin-4-ol (1701-22-0) → C17H10Br2F3NO (1431544-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: phosphorus tribromide / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 2 h / -78 °C

With phosphorus tribromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.02.054

upstream raw materials:

ethyl 4,4,4-trifluoroacetoacetate

4-bromo-aniline

Downstream raw materials:

C₁₇H₁₀Br₂F₃NO

Refernces

• 1、 Yang, Guan-Zhou,Zhu, Jia-Kai,Yin, Xiao-Dan,Yan, Yin-Fang,Wang, Yu-Ling,Shang, Xiao-Fei,Liu, Ying-Qian,Zhao, Zhong-Min,Peng, Jing-Wen,Liu, Hua. "Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids". . p. 11340 - 11353. Retrieved 2019/10/14.