3678-62-4

Basic information

• Product Name: 2-Chloro-4-picoline
• Synonyms: 4-Picoline, 2-chloro-;Pyridine, 2-chloro-4-methyl-;2-CHLORO-GAMMA-PICOLINE;2-CHLOROPICOLINE;2-CHLORO-4-PICOLINE;2-CHLORO-4-METHYLPYRIDINE;2-chloro-4-methylpyrdine;2-Chloro-4-methylpyridine(2-Chloropicoline)
• CAS NO: 3678-62-4
• Molecular Formula: C₆H₆ClN
• Molecular Weight: 127.57
• EINECS: 222-951-2
• Product Categories: Pyridine;pyridine derivative;Halides;Pyridines;Chloropyridines;Halopyridines;pyridine series
• Mol File: 3678-62-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 115°C
• Boiling Point: 194-195 °C(lit.)
• Flash Point: 193 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.456 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.593mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 0.94±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-4-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-picoline(3678-62-4)
• EPA Substance Registry System: 2-Chloro-4-picoline(3678-62-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 3678-62-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid.

Uses

2-Chloro-4-methylpyridine is used as a reagent in the synthesis of the mGLUR5 modulators imidazolyl-ethynyl-pyridines as potential antipsychotics. It is also used in the preparation of trifluoromethyl(pyrimidinyl)azetidinecarboxamides as potent, orally bioavailable TGR5 agonists.

General Description

2-Chloro-4-methylpyridine (2-Chloro-4-picoline) reacts with 3,5-bis(trifluoromethyl)phenylboronic acid to form 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine by palladium-catalyzed cross-coupling reaction.

InChI:InChI=1/C6H6ClN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

Upstream product

• 324028-95-7 6-chloro-4-methylpyridine-2-carboxylic acid 
• 108-89-4 picoline 
• 78948-09-1 acetyl hypofluorite 
• 695-34-1 2-Amino-4-methylpyridine 
• 1003-67-4 4-methylpyridine-1-oxide 
• 1984-23-2 p-nitrophenyl isocyanide 
• 13466-41-6 2-hydroksy-4-methyl-pyridine 
• 153034-86-7 2-chloro-4-iodopyridine 
• 31729-70-1 bis(iodozinc)methane 
• 4021-08-3 4-methylpicolinic acid 
• 26452-80-2 2,4-dichloropyridine 
• 75-16-1 methylmagnesium bromide 
• 624-91-9 methyl nitrite 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 158876-69-8 2-(2-chloropyridin-4-yl)-1-(4-fluorophenyl)ethanone 
• 157329-89-0 2-bromo-6-chloro-4-methylpyridine 
• 583052-20-4 2-(3',5'-bis-trifluoromethylphenyl)-4-methylpyridine 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 102336-07-2 3-(2-methoxypyridin-4-yl)propanoic acid 
• 1187662-57-2 C₆H₅(C₆H₄NC₆H₃)C₅H₃NCH₃ 
• 2732-48-1 4-methyl-2-(phenylthio)pyridine 
• 3475-21-6 4-methyl-2-phenylpyridine 
• 3197-57-7 2-phenacyl-4-methylpyridine 
• 1210867-88-1 2-(benzylsulfanyl)-4-methylpyridine 
• 117523-45-2 OHM 3568 
• 117523-86-1 (4-Methyl-1-oxy-pyridin-2-yl)-(1-phenethyl-piperidin-4-yl)-amine 
• 117523-87-2 1-phenethyl-4-piperidine 
• 1027514-87-9 5-[1-(4-{2-[Methyl-(4-methyl-pyridin-2-yl)-amino]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione 

Relevant articles and documents

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Method for producing 2-chloro-4-trifluoromethylpyridine

The invention discloses a method for producing 2-chloro-4-trifluoromethylpyridine, and belongs to the technical field of fine chemical synthesis. The method comprises the following steps: taking 2-amino-4-methylpyridine as a raw material, and successively carrying out diazotization, chlorination and fluoridation on the 2-amino-4-methylpyridine to obtain 2-chloro-4-trifluoromethylpyridine. The diazotization comprises the following steps: taking the 2-amino-4-methylpyridine as the raw material, and carrying out diazotization on the 2-amino-4-methylpyridine, sodium nitrite and hydrogen chloride in a reactor to obtain 2-chloro-4-methylpyridine. The chlorination comprises the following steps: taking the 2-chloro-4-methylpyridine as the raw material, feeding chlorine and carrying out chlorination to obtain 2-chloro-4-(trichloromethyl) pyridine as a main product and hydrogen chloride as a side product. The fluoridation comprises the following steps: taking the 2-chloro-4-(trichloromethyl) pyridine as the raw material, and carrying out fluoridation on the 2-chloro-4-(trichloromethyl) pyridine and anhydrous hydrogen fluoride in an autoclave to obtain the 2-chloro-4-trifluoromethylpyridine as a main product. Industrial production of the 2-chloro-4-trifluoromethylpyridine is realized.

Chemoselective sp 2-sp3 cross-couplings: Iron-catalyzed alkyl transfer to dihaloaromatics

The chemoselective functionalization of a range of dihaloaromatics with methyl, cyclopropyl, and higher alkyl Grignard reagents via iron-catalyzed cross-coupling is described. The site selectivity of C-X (X = halogen) activation is determined by factors such as the position of the halogen on the ring, the solvent, and the nucleophile. A one-pot protocol for the chemoselective synthesis of mixed dialkyl heterocycles is achieved solely employing iron catalysis.