2-Chloro-3,5-dimethylpyrazine
[CAS# 38557-72-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Chloro-3,5-dimethylpyrazine
• Molecular Formula: C₆H₇ClN₂
• Molecular Weight: 142.59
• CAS Registry Number: 38557-72-1
• EC Number: 696-037-0
• SMILES: CC1=CN=C(C(=N1)C)Cl

Properties

• Solubility: Sparingly soluble (21 g/L) (25 °C), Calc.^*
• Density: 1.184±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 186.6±35.0 °C (760 Torr), Calc.^*
• Flash point: 83.1±11.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Chloro-3,5-dimethylpyrazine is a compound of great interest due to its wide range of applications in industries ranging from pharmaceuticals to food and flavors. 2-Chloro-3,5-dimethylpyrazine was synthesized and characterized for the first time by the reaction of 2,3-dimethylpyrazine with chlorine gas or a chlorinating agent. This synthesis marked a major advance in heterocyclic chemistry and provided a route to chlorinated pyrazine derivatives with unique chemical properties.

The molecular structure of 2-chloro-3,5-dimethylpyrazine consists of a pyrazine ring with a chlorine substituent at the 2-position and methyl groups at the 3- and 5-positions. This arrangement gives it specific chemical properties, including moderate volatility and a unique aroma. The chlorine groups enhance its reactivity, making it valuable in a variety of chemical transformations and applications.

In the flavor and fragrance industry, 2-chloro-3,5-dimethylpyrazine is highly valued for its nutty, roasted, and earthy aromas. It is commonly used as a flavoring agent in foods such as baked goods, savory snacks, and beverages. Its characteristic odor helps enhance the sensory appeal of these products, providing a rich and complex flavor profile.

In the pharmaceutical field, 2-chloro-3,5-dimethylpyrazine is a key intermediate in the synthesis of drug compounds. Its functional groups are able to modify the bioactivity and pharmacokinetic properties of drug molecules. Researchers have explored the potential application of its derivatives in drug discovery programs, focusing on its role in the development of therapeutic agents for various medical conditions.

From a chemical perspective, 2-chloro-3,5-dimethylpyrazine can be used as a building block in organic synthesis. Its reactivity allows the introduction of various functional groups, which helps create novel compounds with customized properties. It is a versatile precursor for the synthesis of complex molecules, including agrochemicals, dyes, and materials used in electronic applications.

Research on 2-chloro-3,5-dimethylpyrazine continues to grow, thanks to its unique chemical properties and wide range of application potential. Future research aims to explore its environmental impact, develop more efficient synthesis methods, and expand its application in emerging fields such as nanotechnology and biotechnology.

References

2018. Alkyl-Dimethylpyrazines in Mandibular Gland Secretions of Four Odontomachus Ant Species (Formicidae: Ponerinae). Journal of Chemical Ecology, 44(3).
DOI: 10.1007/s10886-018-0948-y

2014. Characterization and analysis of structural isomers of dimethyl methoxypyrazines in cork stoppers and ladybugs (Harmonia axyridis and Coccinella septempunctata). Analytical and Bioanalytical Chemistry, 406(22).
DOI: 10.1007/s00216-014-8049-4

2004. Deoxidative Chlorination of Pyrazine N-Oxides. Science of Synthesis.
URL: SD-016-00973