132097-09-7

Basic information

• Product Name: 2,4-Dichloro-3-methylpyridine
• Synonyms: 2,4-Dichloro-3-methylpyridine;2,4-Dichloro-3-picoline;2,4-DICHLORO-3-METHYLPYRIDINE, 98+%
• CAS NO: 132097-09-7
• Molecular Formula: C₆H₅Cl₂N
• Molecular Weight: 162.0166
• Product Categories: Pyridine;Amines;Heterocycles
• Mol File: 132097-09-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 218.708 °C at 760 mmHg
• Flash Point: 106.833 °C
• Appearance: /
• Density: 1.319 g/cm³
• Vapor Pressure: 0.183mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.38±0.10(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-3-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-3-methylpyridine(132097-09-7)
• EPA Substance Registry System: 2,4-Dichloro-3-methylpyridine(132097-09-7)

Safety Data

• Hazardous Substances Data: 132097-09-7(Hazardous Substances Data)

Usage

Description

2,4-Dichloro-3-methylpyridine is an organic compound with the molecular formula C6H5Cl2N. It is a derivative of pyridine, featuring two chlorine atoms at the 2nd and 4th positions and a methyl group at the 3rd position. 2,4-Dichloro-3-methylpyridine serves as a key intermediate in the synthesis of various pharmaceuticals and chemical products due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-3-methylpyridine is used as a chemical intermediate for the preparation of imidazo[4,5-b]pyridine derivatives. These derivatives are specifically designed for the treatment of diseases caused by gastric acid. The compound plays a crucial role in the development of medications that target and alleviate the symptoms associated with excessive stomach acid production.

InChI:InChI=1/C6H5Cl2N/c1-4-5(7)2-3-9-6(4)8/h2-3H,1H3

Upstream product

• 74-88-4 methyl iodide 
• 91668-83-6 2-Chloro-3-methylpyridine N-oxide 
• 26452-80-2 2,4-dichloropyridine 
• 18368-76-8 2 chloro-3-methylpyridine 

Downstream Products

• 945543-26-0 3-(bromomethyl)-2,4-dichloropyridine 

Relevant articles and documents

Effects of the pyridine 3-substituent on regioselectivity in the nucleophilic aromatic substitution reaction of 3-substituted 2,6-dichloropyridines with 1-methylpiperazine studied by a chemical design strategy

A chemical design strategy has been used to select 3-substituted 2,6-dichloropyridines for the nucleophilic aromatic substitution reaction with 1-methylpiperazine. The aim was to study the dependency of the regioselectivity in these reactions on the character of the pyridine 3-substituent expressed by their lipophilicity (PI), size (MR), and inductive effect (Ip). Interestingly, the regioselectivity did not correlate with any of these parameters, but in a statistically significant manner with the Verloop steric parameter B1, as indicated by the p value of 0.006 (R2 = 0.45). This implies that bulky 3-substituents close to the pyridine ring induce regioselectivity towards the 6-position. Useful in practical synthesis is the different regioselectivity obtained with a carboxylic acid 3-substituent and precursors or derivatives thereof. Thus, in acetonitrile as solvent, 3-carboxylate and 3-amide substituents were preferred to obtain the 2-isomer (9:1 ratio of the 6-isomer), whereas the 3-cyano and 3-trifluoromethyl substitutents were preferred to obtain the 6-isomer (9:1 ratio of the 2-isomer). Analysis of the regioselectivity Rsel for the pyridine 2-position in the reaction of 2,6-dichloro-3-(methoxycarbonyl)pyridine with 1-methylpiperazine in 21 different solvents showed that Rsel could be predicted by the Kamlet-Taft equation: Rsel = 1.28990 + 0.03992α - 0.59417β - 0.46169π* (R2 = 0.95, p = 1.9 × 10-10). Rsel is thus mainly correlated with the ability of the solvent to function as a hydrogen-bond acceptor, as expressed by the solvatochromic β parameter. Thus, the 16:1 regioselectivity for the 2-isomer in DCM (β = 0.10) could be switched to a 2:1 selectivity for the 6-isomer in DMSO (β = 0.76). Copyright

IMIDAZOPYRIDINE COMPOUND

A compound represented by the following general formula (1), or a salt or hydrate thereof: wherein R1 represents a C1-C6 alkyl group or C2-C6 alkynyl group which may be substituted, or a phenyl group which may be substituted, R2 represents a hydrogen atom or a C1-C6 alkyl group, R3 represents methyl or ethyl group, R4 represents a C1-C6 alkyl group, R5 represents a hydrogen atom, provided that a compound wherein R1 is a C1-C6 alkyl group unsubstituted or substituted with a halogen atom and R2 is a hydrogen atom is excluded.