175205-81-9

Basic information

• Product Name: 2-Bromo-4-(trifluoromethyl)pyridine
• Synonyms: 2-BROMO-4-(TRIFLUOROMETHYL)PYRIDINE;Pyridine, 2-broMo-4-(trifluoroMethyl)-;2-Bromo-alpha,alpha,alpha-trifluoro-4-picoline
• CAS NO: 175205-81-9
• Molecular Formula: C₆H₃BrF₃N
• Molecular Weight: 225.99
• EINECS: 1312995-182-4
• Product Categories: Halides;Pyridines;Pyridine;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 175205-81-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: -21--20 °C
• Boiling Point: 84-85 °C14 mm Hg
• Flash Point: 164 °F
• Appearance: /
• Density: 1.827 g/mL at 25 °C
• Vapor Pressure: 0.622mmHg at 25°C
• Refractive Index: n20/D 1.478
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.57±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-4-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-(trifluoromethyl)pyridine(175205-81-9)
• EPA Substance Registry System: 2-Bromo-4-(trifluoromethyl)pyridine(175205-81-9)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38-37/38-36
• Safety Statements: 26-36/37-45-37
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 175205-81-9(Hazardous Substances Data)

Usage

Description

2-Bromo-4-(trifluoromethyl)pyridine is an organic compound characterized by the presence of a bromine atom at the 2nd position and a trifluoromethyl group at the 4th position on a pyridine ring. It is a valuable intermediate in the synthesis of various pharmaceuticals and chemical compounds due to its unique structural features and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-(trifluoromethyl)pyridine is used as a key intermediate for the synthesis of pyrazolopyridines, which serve as kinase LRRK2 inhibitors. These inhibitors are crucial in the treatment and prevention of cancer and neurodegenerative diseases, such as Parkinson's disease, due to their ability to modulate the activity of the LRRK2 enzyme.
Used in Chemical Synthesis:
2-Bromo-4-(trifluoromethyl)pyridine is used as a starting material for the preparation of nicotinic acid derivatives through a regioselective deprotonation at the C-3 position with LDA (lithium diisopropylamide) followed by trapping with carbon dioxide. This process allows for the synthesis of a variety of nicotinic acid analogs, which have potential applications in various fields, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C6H3BrF3N/c7-5-4(6(8,9)10)2-1-3-11-5/h1-3H

Upstream product

• 81565-18-6 2-chloro-4-trifluoromethyl pyridine 

Downstream Products

• 1171919-08-6 ethyl 4-(trifluoromethyl)picolinate 
• 3796-24-5 4-trifluoromethylpyridine 
• 940289-80-5 2-phenyl-4-(trifluoromethyl)pyridine 
• 208720-09-6 2-(1-methylhydrazinyl)-4-(trifluoromethyl)-pyridine 
• 588702-62-9 4-(trifluoromethyl)-2-pyridinecarboxylic acid 
• 1101205-35-9 2-biphenyl-4-yl-5-(trifluoromethyl)pyridine 

Relevant articles and documents

Method For Producing Substituted Halopyridines

Methods for producing substituted halopyridines (II) by reacting a β-hydroxy-y-acyl butyronitrile (I) or a suitable acyl-protected derivative with hydrogen halides, or substances or mixtures that can release hydrogen halides. In the formulae (I) and (II): R, R4 represent H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl group, or optionally a substituted heteroaryl group; R1, R2, R3 represent H, a linear or branched alkyl group, optionally a substituted aryl, aralkyl, optionally a substituted heteroaryl group or one of the following groups CnH(2n+1?m)Xm, COOR, or CN; R5 represents H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl, optionally a substituted heteroaryl or one of the following groups CnH(2n+1?m)Xm, COOR, CN, SO2R, SOR, PO(OR)2; n represents a positive whole number; m represents a positive whole number ≦2n+1; and X represents F, Cl, Br, or I.

Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).