109371-18-8

Basic information

• Product Name: 4-Chloro-2,3,5-trimethylpyridine
• Synonyms: 4-Chloro-2,3,5-trimethylpyridine
• CAS NO: 109371-18-8
• Molecular Formula: C₈H₁₀ClN
• Molecular Weight: 155.62
• Product Categories: API intermediates
• Mol File: 109371-18-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Chloro-2,3,5-trimethylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2,3,5-trimethylpyridine(109371-18-8)
• EPA Substance Registry System: 4-Chloro-2,3,5-trimethylpyridine(109371-18-8)

Safety Data

• Hazardous Substances Data: 109371-18-8(Hazardous Substances Data)

Usage

General Description

4-Chloro-2,3,5-trimethylpyridine, also known as 2,3,5-Trimethyl-4-chloropyridine, is a chemical compound with the molecular formula C8H10ClN. It is a chlorinated derivative of pyridine and is a pale yellow liquid at room temperature. 4-Chloro-2,3,5-trimethylpyridine is primarily used as a building block in organic synthesis and can also be used as an intermediate in the production of agricultural chemicals, pharmaceuticals, and dyes. It is considered to be a hazardous chemical and should be handled with caution due to its potential harmful effects on health and the environment.

Upstream product

• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 109371-16-6 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 
• 109371-20-2 4-chloro-2,3,5-trimethylpyridine 1-oxide 
• 109371-17-7 2,4-dichloro-3,5,6-trimethylpyridine 

Downstream Products

• 109371-19-9 4-methoxy-2,3,5-trimethylpyridine 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 109371-20-2 4-chloro-2,3,5-trimethylpyridine 1-oxide 

Relevant articles and documents

Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.

A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.