95-89-6

Basic information

• Product Name: 3-CHLORO-2,5-DIMETHYLPYRAZINE
• Synonyms: 3-CHLORO-2,5-DIMETHYL-1,4-DIAZINE;3-CHLORO-2,5-DIMETHYLPIAZINE;3-CHLORO-2,5-DIMETHYLPYRAZINE;Pyrazine, 3-chloro-2,5-dimethyl-;2,5-Dimethyl-3-chloropyrazine;3-Chloro-2,5-diMethylpyrazine 98%;3-Chloro-2,5-diMethylpyrazine, 97+%
• CAS NO: 95-89-6
• Molecular Formula: C₆H₇ClN₂
• Molecular Weight: 142.59
• EINECS: 202-463-6
• Product Categories: Pyrazines;Mono- & Polyalkylpyrazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrazinesHeterocyclic Building Blocks
• Mol File: 95-89-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 66-69 °C9 mm Hg(lit.)
• Flash Point: 182 °F
• Appearance: Colorless to brown liquid
• Density: 1.181 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.22mmHg at 25°C
• Refractive Index: n20/D 1.527(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-CHLORO-2,5-DIMETHYLPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-2,5-DIMETHYLPYRAZINE(95-89-6)
• EPA Substance Registry System: 3-CHLORO-2,5-DIMETHYLPYRAZINE(95-89-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: UQ2462000
• Hazardous Substances Data: 95-89-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown liquid

Uses

3-Chloro-2,5-dimethylpyrazine participates in cross-coupling reactions involving chlroropyrazines with 1-substituted indoles. Occasionally this reaction is catalyzed by iron.

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

Upstream product

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

Downstream Products

• 33870-84-7 5-chloro-3,6-dimethyl-2(1H)-pyrazinone 
• 165601-62-7 2-butyl-4-(3,6-dimethylpyrazin-2-yl)-1-<<2'-<1-(triphenylmethyl)-1H-tetrazol-5-yl><1,1'-biphenyl>-4-yl>methyl>-1H-imidazole 
• 59215-42-8 4-(3,6-dimethylpyrazinyl)piperazine 
• 72668-36-1 (±)-2,5-dimethyl-3-(2-methylbutyl)pyrazine 
• 32736-94-0 2,5-dimethyl-3-(2-methylpropyl)pyrazine 
• 106860-97-3 2,5-dimethyl-3-phenyl-pyrazine 
• 19846-22-1 3-methoxyl-2,5-dimethylpyrazine 

Relevant articles and documents

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.

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.

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.