2-Bromo-3-chloro-5-(trifluoromethyl)pyridine

Base Information

• Chemical Name: 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine
• CAS No.: 75806-84-7
• Molecular Formula: C6H2BrClF3N
• Molecular Weight: 260.441
• Hs Code.: 29333990
• European Community (EC) Number: 680-932-8
• DSSTox Substance ID: DTXSID40371226
• Wikidata: Q72453733
• Mol file: 75806-84-7.mol

Synonyms:2-Bromo-3-chloro-5-(trifluoromethyl)pyridine;75806-84-7;MFCD00153072;Pyridine, 2-bromo-3-chloro-5-(trifluoromethyl)-;SCHEMBL2596379;DTXSID40371226;BCP11664;BBL103219;STL557029;AKOS005071425;AB04058;AC-9339;CS-W002440;SY016457;2-bromo-3-chloro-5-trifluoromethylpyridine;2-bromo-3-chloro-5(trifluoromethyl)pyridine;2-bromo-3-chloro-5-trifluoromethyl-pyridine;A9627;AM20061489;B4603;FT-0611413;9F-069;EN300-192011;4-Chloro-2-(trifluoroacetyl)anilinehydrochloride;J-508204

Chemical Property of 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine

Chemical Property:

• Vapor Pressure: 0.783mmHg at 25°C
• Refractive Index: 1.38
• Boiling Point: 226.921 °C at 760 mmHg
• PKA: -3.92±0.20(Predicted)
• Flash Point: 91.039 °C
• PSA: 12.89000
• Density: 1.805 g/cm³
• LogP: 3.51630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 258.90112
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

98%, ^*data from raw suppliers

2-Bromo-3-chloro-5-(trifluoromethyl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Cl)Br)C(F)(F)F

Technology Process of 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine

There total 3 articles about 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine 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: 90.0%

2,3-dichloro-5-trifluoromethylpyridine (69045-84-7) → 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (75806-84-7)

Guidance literature:

With trimethylsilyl bromide; at 100 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol4030925

Reference yield: 58.0%

3-chloro-5-(trifluoromethyl)-2-hydroxypyridine (76041-71-9) → 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (75806-84-7)

Guidance literature:

With phosphorus(V) oxybromide; at 150 ℃; for 6h; Temperature;

Reference yield:

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (75806-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen fluoride; sulfur tetrafluoride / 12 h / 100 °C / 1125.11 Torr / Autoclave

2: N-chloro-succinimide / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 8 h / 20 °C

3: phosphorus(V) oxybromide / 6 h / 150 °C

With N-chloro-succinimide; sulfur tetrafluoride; hydrogen fluoride; phosphorus(V) oxybromide; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide;

upstream raw materials:

2,3-dichloro-5-trifluoromethylpyridine

6-hydroxy-3-pyridinecarboxylic acid

3-chloro-5-(trifluoromethyl)-2-hydroxypyridine

Downstream raw materials:

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]aniline

3-chloro-2-cyano-5-(trifluoromethyl)pyridine

5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

5-(3,5-dimethoxyphenyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Refernces

• 1、 Tsoung, Jennifer,Panteleev, Jane,Tesch, Matthias,Lautens, Mark. "Multicomponent-multicatalyst reactions (MC)2R: Efficient dibenzazepine synthesis". supporting information. p. 110 - 113. Retrieved 2014/01/23.