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

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

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-picoline is used as a reagent for the synthesis of mGLUR5 modulators, specifically imidazolyl-ethynyl-pyridines, which have potential applications as antipsychotics. Its role in the development of these compounds is crucial due to its ability to participate in palladium-catalyzed cross-coupling reactions, leading to the formation of the desired antipsychotic agents.
Additionally, 2-Chloro-4-picoline is used in the preparation of trifluoromethyl(pyrimidinyl)azetidinecarboxamides, which are potent, orally bioavailable TGR5 agonists. These compounds have potential therapeutic applications in the treatment of various metabolic disorders and conditions related to bile acid metabolism.

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 
• 13466-41-6 4-methyl-1H-pyridin-2-one 
• 13466-41-6 2-hydroksy-4-methyl-pyridine 
• 10026-13-8 phosphorus pentachloride 
• 1003-67-4 4-methylpyridine-1-oxide 
• 1984-23-2 p-nitrophenyl isocyanide 
• 624-91-9 methyl nitrite 
• 26452-80-2 2,4-dichloropyridine 
• 75-16-1 methylmagnesium bromide 
• 153034-86-7 2-chloro-4-iodopyridine 
• 31729-70-1 bis(iodozinc)methane 

Downstream Products

• 1620-76-4 2-Cyano-4-methylpyridin 
• 52313-61-8 2-chloro-4-methylpyridin-N-oxide 
• 75390-50-0 4-methyl-2-phenoxypyridine 
• 100848-70-2 2-methoxy-4-methyl-pyridine 
• 152191-21-4 1-(benzenesulfonyl)-2-(4-methyl-2-pyridyl)indole 
• 73282-13-0 1,1'-bis-benzenesulfonyl-1H,1'H-[2,2']biindolyl 
• 102336-06-1 2-phenylmethyloxy-4-methylpyridine 
• 526184-60-1 2-(2-aminoethylamino)-4-methylpyridine 
• 158876-69-8 2-(2-chloropyridin-4-yl)-1-(4-fluorophenyl)ethanone 
• 157329-89-0 2-bromo-6-chloro-4-methylpyridine 
• 681831-94-7 ethyl 2-(4-methylpyridin-2-yl)benzoate 
• 583052-20-4 2-(3',5'-bis-trifluoromethylphenyl)-4-methylpyridine 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 581098-29-5 1-(2-chloropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione 1-oxime 

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.

Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound

The invention provides a preparation method of a non-transition metal-catalyzed 2-halogenated pyridine compound. The 2-halogenated pyridine compound is an important component of many medicines and bioactive molecules and has important application in the fields of organic synthesis, medicinal chemistry and the like and wide market prospects. The invention relates to the preparation method of the non-transition metal-catalyzed 2-halogenated pyridine compound. According to the method, pyridine-2-carboxylic acid, derivatives of the pyridine-2-carboxylic acid, NaF, KF, CsF, TBAF, NaCl, KCl, CsCl, TBAC, NCS, NaBr, KBr, CsBr, Br2, TBAB, NBS, NaI, KI, CsI, I2 and NIS are used as raw materials, and under the presence of base and an accelerant and mild conditions, the 2-halogenated pyridine compoundis synthesized. The method has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction conditions are mild and the like; the method has great use value and socialand economic benefits.

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.

Preparation of an Arenylmethylzinc Reagent with Functional Groups by Chemoselective Cross-Coupling Reaction of Bis(iodoazincio)methane with Iodoarenes

Palladium-catalyzed cross-coupling reaction of bis(iodozincio)methane with iodoarenes carrying various functionalities such as ester, boryl, cyano, and halo groups proceeded chemoselectively to give the corresponding arenylmethylzinc species efficiently. The moderate reactivity of the gem-dizinc reagent imparted functional group tolerance to the process. The transformations from iodoheteroarenes were also performed; in the case of iodopyridine derivatives, the nickel-catalyzed reaction gave the corresponding organozinc species efficiently. The obtained arenylmethylzinc species underwent the copper-mediated coupling reaction with a range of organic halides.

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.

BACTERICIDE COMPOSITION AND METHOD OF CONTROLLING PLANT DISEASE

It is to provide a fungicidal composition having stable and high fungicidal effects against cultivated crops infected with plant diseases resulting from plant diseases. A fungicidal composition containing as active ingredients (a) a benzoylpyridine derivative represented by the formula (I) or its salt: (wherein X is a halogen atom, a nitro group, a substitutable hydrocarbon group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group, a hydroxyl group, a substitutable alkylthio group, a cyano group, a carboxyl group which may be esterified or amidated, or a substitutable amino group, n is 1, 2, 3 or 4; R1 is a substitutable alkyl group, R2' is a substitutable alkyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group or a hydroxyl group, p is 1, 2 or 3, and R2" is a substitutable alkoxy group or a hydroxyl group, provided that at least two of R2' and R2" may form a condensed ring containing an oxygen atom) and (b) at least one another fungicide.

Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides

Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.

Stabilised 2,3-pyridyne reactive intermediates of exceptional dienophilicity

The enhanced dienophilicity of 4-methoxy, 4-aryloxy and 4-thiophenoxy analogues 6-9 of 2,3-pyridyne (2) relative to 2 itself is reported. The regioselective lithiation of 4-alkoxy-(22, 23 and 25) and 4-thiophenoxy-2- chloropyridme (24) at low temperatures, followed by elimination of lithium chloride affords 4-alkoxy- and 4-thiophenoxypyridynes, which can be trapped in situ in a [4+2] cycloaddition reaction with furan to give endoxides 28-31 in moderate to good yields (25-58%). In contrast, precursors with a hydrogen (18) or methyl (12) substituent at C-4 give no evidence for pyridyne formation under these conditions. Attempts to generate 6-isopropoxy-2,3-pyridyne (10) from the low-temperature lithiation of 2-chloro-6-isopropoxypyridine were unsuccessful due to the instability of the 2-chloro-6-isopropoxy-5-lithiopyridine. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene

Diphosgene and triphosgene in the presence of amines were found to be an excellent chlorinating agents with high selectivity for the preparation of chloromethylpyridines and chloropyridines from picoline-N-oxides and pyridine-N-oxides respectively.

Side-chain retention during lithiation of 4-picoline and 3,4-lutidine: Easy access to molecular diversity in pyridine series

The first direct ring-selective lithiation of 4-picoline and 3,4-lutidine has been achieved through the use of BuLi/LiDMAE aggregates to prevent the usual side-chain metallation. Several functionalities have been introduced at the C-2, C-6 and C-5 positions by ring-selective sequential lithiation, opening a simple and fast route to polysubstituted pyridine building blocks. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.