2-Bromo-5-(trifluoromethyl)pyridine

Base Information

• Chemical Name: 2-Bromo-5-(trifluoromethyl)pyridine
• CAS No.: 50488-42-1
• Molecular Formula: C6H3BrF3N
• Molecular Weight: 225.996
• Hs Code.: 29333990
• European Community (EC) Number: 628-661-6
• DSSTox Substance ID: DTXSID20371360
• Nikkaji Number: J1.688.881H
• Wikidata: Q69757717
• Mol file: 50488-42-1.mol

Synonyms:2-Bromo-5-(trifluoromethyl)pyridine;50488-42-1;2-bromo-5-trifluoromethylpyridine;2-bromo-5-trifluoromethyl-pyridine;2-Bromo-5-Trifluoromethyl Pyridine;MFCD00153086;PYRIDINE, 2-BROMO-5-(TRIFLUOROMETHYL)-;5-(trifluoromethyl)-2-bromopyridine;2-Brom-5-(trifluormethyl)pyridin;6-Bromo-3-trifluoromethylpyridine;2-Bromo-5-trilfuoromethylpyridine;SCHEMBL67213;5-trifluoromethyl-2-bromopyridine;DTXSID20371360;QWISXWNESLHVBD-UHFFFAOYSA-N;RB1670;2-bromo-5-(trifluoromethyl)-pyridine;2-Bromo-5-(trifluoromethyl) pyridine;AKOS005063713;AB04065;AC-9487;CS-W008678;FG-0478;2-Bromo-5-(trifluoromethyl)pyridine, 97%;A7486;AM20061263;FT-0611472;EN300-68433;Q-101247;Z415645014

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

Chemical Property:

• Appearance/Colour: Light yellow needles
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 44-48 °C
• Refractive Index: 1.572
• Boiling Point: 209.3 °C at 760 mmHg
• PKA: -1?+-.0.10(Predicted)
• Flash Point: 80.4 °C
• PSA: 12.89000
• Density: 1.707 g/cm³
• LogP: 2.86290
• Storage Temp.: Room temperature.
• Solubility.: Soluble in methanol and ethanol.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 224.94010
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T, Xi, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=NC=C1C(F)(F)F)Br
• Uses: 2-Bromo-5-(trifluoromethyl)pyridine is substrate used in a palladium-catalyzed α-arylation of a Refomatsky reagent. 2-Bromo-5-(trifluoromethyl)pyridine is a substrate used in a palladium-catalyzed α-arylation of a Refomatsky reagent.

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

There total 3 articles about 2-Bromo-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: 76.0%

2-chloro-5-trifluoromethylpyridine (52334-81-3) → 2-bromo-5-(trifluoromethyl)pyridine (50488-42-1)

Guidance literature:

With trimethylsilyl bromide; In various solvent(s); for 20h; Heating;

DOI:10.1002/ejoc.200390215

Reference yield: 29.0%

2-bromo-5-iodo-pyridine (73290-22-9) + (trifluoromethyl)trimethylsilane (81290-20-2) → 2-bromo-5-(trifluoromethyl)pyridine (50488-42-1)

Guidance literature:

With potassium fluoride; copper(l) iodide; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 25 ℃; for 6h;

DOI:10.1002/1099-0690(20021)2002:2<327::AID-EJOC327>3.0.CO;2-V

Reference yield:

2,5-dibromopyridine (624-28-2) → 2-bromo-5-(trifluoromethyl)pyridine (50488-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / hexane; diethyl ether / 0.75 h / -75 °C

1.2: 84 percent / I₂ / hexane; tetrahydrofuran; diethyl ether / 0.75 h / -75 °C

2.1: 29 percent / KF; CuI / dimethylformamide; 1-methyl-pyrrolidin-2-one / 6 h / 25 °C

With potassium fluoride; copper(l) iodide; n-butyllithium; In 1-methyl-pyrrolidin-2-one; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(20021)2002:2<327::AID-EJOC327>3.0.CO;2-V

upstream raw materials:

2-bromo-5-iodo-pyridine

(trifluoromethyl)trimethylsilane

2-chloro-5-trifluoromethylpyridine

2,5-dibromopyridine

Downstream raw materials:

5-(trifluoromethyl)picolinic acid

2-cyano-5-trifluoro-methylpyridine

3-chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acid ethyl ester

(3R)-3-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]piperazine

Refernces

• 1、 Cottet, Fabrice,Schlosser, Manfred. "Trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper". . p. 327 - 330. Retrieved 2007/10/03.