95-89-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-2,5-dimethylpyrazine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its participation in cross-coupling reactions with 1-substituted indoles allows for the creation of complex organic molecules with potential therapeutic applications.
Used in Organic Synthesis:
3-Chloro-2,5-dimethylpyrazine is utilized as a key building block in organic synthesis, particularly for the preparation of novel heterocyclic compounds. Its reactivity in cross-coupling reactions enables the formation of diverse chemical structures with potential applications in various fields, such as materials science and agrochemicals.
Used in Catalyst Development:
The occasional use of iron as a catalyst in the cross-coupling reactions involving 3-chloro-2,5-dimethylpyrazine highlights its potential role in the development of new and efficient catalysts. This can contribute to advancements in green chemistry and sustainable synthetic processes.

InChI:InChI=1/C8H11ClN2/c1-3-6-5-10-7(4-2)8(9)11-6/h5H,3-4H2,1-2H3

Upstream product

• 6890-37-5 2,5-dimethyl-pyrazine 1-oxide 
• 16289-18-2 3,6-dimethyl-1H-pyrazin-2-one 
• 5625-46-7 cyclo(-DL-Ala-DL-Ala-) 
• 930-62-1 2,4-Dimethylimidazole 
• 67-66-3 chloroform 
• 5625-46-7 (+/-)-cis-3,6-dimethyl-piperazine-2,5-dione 
• 123-32-0 2,5-dimethyl-pyrazine 
• 930-61-0 2,4-dimethyl-2-imidazoline 

Downstream Products

• 54290-13-0 (E)-2,5-dimethyl-3-stytylpyrazines 
• 131602-73-8 2-methoxycarbonyl-3,6-dimethylpyrazine 
• 135763-84-7 2-cyclohexylthio-3,6-dimethylpyrazine 
• 125031-65-4 2-(3,6-Dimethyl-pyrazin-2-yl)-1-(toluene-4-sulfonyl)-1H-indole 
• 125031-61-0 3-(3,6-Dimethyl-pyrazin-2-yl)-1-(toluene-4-sulfonyl)-1H-indole 
• 125031-84-7 1-benzyl-2-(3,6-dimethylpyrazin-2-yl)indole 
• 141994-98-1 2,5-Dimethyl-3-(1H-pyrrol-3-yl)-pyrazine 
• 141994-93-6 2,5-Dimethyl-3-(1H-pyrrol-2-yl)-pyrazine 
• 141994-97-0 3-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-2,5-dimethyl-pyrazine 
• 141994-96-9 3-(1-Benzenesulfonyl-1H-pyrrol-2-yl)-2,5-dimethyl-pyrazine 
• 14667-55-1 2,3,5-trimethylpyrazine 
• 123-32-0 2,5-dimethyl-pyrazine 
• 13360-65-1 2-ethyl-3,6-dimethylpyrazine 
• 2435-47-4 2-Cyano-3,6-dimethylpyrazin 

Relevant academic research and scientific papers

The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: A semiochemical in orchid pollination

Drakaea livida (Orchidaceae) is pollinated by sexual deception of the wasp Zaspilothynnus nigripes (Thynnidae). It is shown that the orchid emits the same compound, 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine, that females emit when calling for mates. This novel pyrazine was isolated and identified by GC-EAD and GC-MS and confirmed by synthesis. This compound may represent the first known case of pyrazines as sex pheromones in Hymenoptera.

Pheromone synthesis. Part 261: Synthesis of four pyrazines produced by females of the Korean apricot wasp, Eurytoma maslovskii

Four pyrazines were synthesized as sex specific volatiles of female Korean apricot wasp, Eurytoma maslovskii. They are 2,5-dimethyl-3-vinylpyrazine (1), 2,5-dimethyl-3-(2-methylpropyl)pyrazine (2), 2,5-dimethyl-3-(2-methylbutyl)pyrazine (3), and 2,5-dimethyl-3-(3-methylbutylpyrazine (4). They were synthesized in 74–85% yields by Pd- or Fe-catalyzed cross-coupling reactions between 3-chloro-2,5-dimethylpyrazine and CH2=CHBF3K or RMgBr. The present synthesis of 1 is the most reliable and scalable one to date.

Pyrazine biosynthesis in corynebacterium glutamicum

The volatile compounds released by Corynebacterium glutamicum were collected by use of the CLSA technique (closed-loop stripping apparatus) and analysed by GC-MS. The headspace extracts contained several acyloins and pyrazines that were identified by their synthesis or comparison to commercial standards. Feeding experiments with [2H7]acetoin resulted in the incorporation of labelling into trimethylpyrazine and tetramethylpyrazine. Several deletion mutants targeting genes of the primary metabolism, were constructed to elucidate the biosynthetic pathway to pyrazines in detail. A deletion mutant of the ketol-acid reductoisomerase was not able to convert the acetoin precursor (S)2-acetolactate into the pathway intermediate (R)-2,3-dihydroxy-3-methylbutanoate to the branched amino acids. This mutant requires valine, leucine, and isoleucine for growth and produces significantly higher amounts and more different compounds of the acyloin and pyrazine classes. Gene deletion of the acetolactate synthase (AS) resulted in a mutant that is not able to convert pyruvate into (5)-2-acetolactate. This mutant also requires branched amino acids and produces only very small amounts of pyrazines likely from valine via the valine biosynthetic pathway operating in reverse order. A ΔASΔKR double mutant was constructed that does not produce any pyrazines at all. These results open up a detailed biosynthetic model for the formation of alkylated pyrazines via acyloins.

Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones

The synthesis of trialkylpyrazines having methyl groups on C-2 and C-5 is described, which is completed by the cross-coupling reaction of 2-chloro-3,6-dimethylpyrazine with dialkylzinc in the presence of [1,3-bis(diphenylphosphino)propane] nickel(II) chloride. Similarly, 2,5-diisobutyl-, -diisopropyl- and -di-sec-butyl-3-methylpyrazines are prepared from the corresponding dialkyl chloropyrazlnes. The dimethyl products are acylated with an α-keto acid under the Minisci radical conditions providing 2-acyl-5-alkyl-3,6-dimethylpyrazines. Several compounds obtained in this study prove to be active as components of pheromones in ants.

Reactions of Halogenomethanes in the Vapor Phase. Part 4. The Reactions of Imidazoles with Chloroform at 550 deg C, and a Comparison with their Liquid-phase Reactions with Trichloroacetate Ion or Hexachloroacetone and Base

1-Unsubstituted imidazoles and chloroform at 550 deg C in a flow system give mainly 5-chloropyrimidines, together with 4-chloropyrimidines and chloropyrazines.The effects of methyl substituents on the ratio of products is considered.The liquid-phase reactions of 2-methyl- and 2,4,5-trimethyl-imidazole under conditions in which dichlorocarbene is said to be formed in basic or neutral conditions were studied, and compared with the gas-phase reactions with chloroform.

Reactions of Halogenomethanes in the Vapour Phase. Part 5. The Reactions of Imidazolines, Anils, and 1-Methylimidazole with Chloroform at 550 deg C, and a Comparison with their Liquid-Phase Reactions with Trichloroacetate Ion or Hexachloroacetone and Base

The vapor-phase reactions of imidazolines and anils with chloroform at 550 deg C are compared with their liquid-phase reactions in the presence of hexachloroacetone and base or upon thermolysis with trichloroacetate ion.In the vapour-phase reactions imidazolines, unlike imidazoles, gave non-chlorinated pyrimidines, and 1-methyl-imidazole gave 2-cyanopyrrole and the four 3-chlorocyanopyridines.