81831-67-6

Basic information

• Product Name: 2-(CHLOROMETHYL)-3-METHYLPYRAZINE
• Synonyms: 2-(CHLOROMETHYL)-3-METHYLPYRAZINE;Pyrazine, 2-(chloroMethyl)-3-Methyl-
• CAS NO: 81831-67-6
• Molecular Formula: C6H7ClN2
• Molecular Weight: 142.58618
• Mol File: 81831-67-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(CHLOROMETHYL)-3-METHYLPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-3-METHYLPYRAZINE(81831-67-6)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-3-METHYLPYRAZINE(81831-67-6)

Safety Data

• Hazardous Substances Data: 81831-67-6(Hazardous Substances Data)

Usage

General Description

2-(Chloromethyl)-3-methylpyrazine is a chemical compound with the formula C6H8N2Cl. It is a pyrazine derivative that is commonly used as a flavoring agent in the food industry, particularly in the production of savory and meaty flavors. It is a clear, colorless to pale yellow liquid that has a molecular weight of 146.59 g/mol. 2-(Chloromethyl)-3-methylpyrazine is known for its strong, earthy, and nutty aroma and is often used to enhance the savory or umami characteristics of various food products. Additionally, it has been used in the development of pharmaceuticals and can be found in certain cosmetics and personal care products.

Upstream product

• 5910-89-4 2,3-dimethylpyrazine 
• 65464-21-3 2,3-dimethyl-1,4-diazine N-oxide 

Relevant articles and documents

Preparation method of aminomethylpyrazine compound

The invention relates to a preparation method of an aminomethylpyrazine compound, which comprises the following steps of: by taking 2, 3-dimethylpyrazine as an initial raw material, under the initiation of AIBN, adding NCS (N-Chlorosuccinimide) in batches to realize monochlorination, then carrying out Gabriel reaction to obtain 2-methyl-3-aminomethylpyrazine, and then carrying out trifluoroacetylation and polyphosphoric acid cyclization to obtain 8-methyl-3-(trifluoromethyl) imidazole [1, 5-a] pyrazine.

Design, synthesis, and cytotoxic analysis of novel hederagenin–pyrazine derivatives based on partial least squares discriminant analysis

Hederagenin (He) is a novel triterpene template for the development of new antitumor compounds. In this study, 26 new He–pyrazine derivatives were synthetized in an attempt to develop potent antitumor agents; they were screened for in vitro cytotoxicity against tumor and non-tumor cell lines. The majority of these derivatives showed much stronger cytotoxic activity than He. Remarkably, the most potent was compound 9 (half maximal inhibitory concentration (IC50) was 3.45 ± 0.59 μM), which exhibited similar antitumor activities against A549 (human non-small-cell lung cancer) as the positive drug cisplatin (DDP; IC50 was 3.85 ± 0.63 μM), while it showed lower cytotoxicity on H9c2 (murine heart myoblast; IC50 was 16.69 ± 0.12 μM) cell lines. Compound 9 could induce the early apoptosis and evoke cell-cycle arrest at the synthesis (S) phase of A549 cells. Impressively, we innovatively introduced the method of cluster analysis modeled as partial least squares discriminant analysis (PLS-DA) into the structure–activity relationship (SAR) evaluation, and SAR confirmed that pyrazine had a profound effect on the antitumor activity of He. The present studies highlight the importance of pyrazine derivatives of He in the discovery and development of novel antitumor agents.

Syntheses and Reactions of Some 2,3-Disubstituted Pyrazine Monoxides

The reactions of 2,3-dimethyl- (4), 2,3-diphenyl- (6), and 2-methyl-3-phenyl-pyrazine monoxides (8 and 9) with phosphoryl chloride and acetic anhydride resulted in giving monochloro- and monoacetoxy-pyrazines in almost all cases.However, the reaction of 6 with acetic anhydride afforded exceptionally a diacetoxydihydropyrazine.These products were converted further to hydroxy or dichloro derivatives.