2-Secbutylpyrazine
[CAS# 124070-52-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Secbutylpyrazine
• Synonyms: 2-butan-2-ylpyrazine
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• CAS Registry Number: 124070-52-6
• SMILES: CCC(C)C1=NC=CN=C1

Properties

• Solubility: 2123 mg/L (25 ºC water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.491, Calc.^*
• Melting point: 21.53 ºC
• Boiling Point: 191.4±20.0 ºC (760 mmHg), Calc.^*, 197.51 ºC
• Flash Point: 71.1±13.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

2-Secbutylpyrazine is an organic compound with the molecular formula C8H10N2. This heterocyclic compound features a pyrazine ring, a six-membered aromatic ring containing two nitrogen atoms at non-adjacent positions. The compound is of interest due to its distinct aromatic profile and its applications in the food and fragrance industries. Its discovery dates back to the mid-20th century when various pyrazine derivatives were being studied for their unique olfactory properties.

The synthesis of 2-secbutylpyrazine can be achieved through various methods, including the alkylation of pyrazine with sec-butyl halides. In the laboratory, 2-secbutylpyrazine can be synthesized from the reaction of pyrazine with sec-butyl bromide or iodide in the presence of a suitable base, such as potassium carbonate. This reaction typically proceeds via nucleophilic substitution, allowing the attachment of the sec-butyl group to the pyrazine ring.

2-Secbutylpyrazine is primarily recognized for its distinct aroma, described as earthy, nutty, and roasted. This characteristic scent makes it a valuable compound in the flavor and fragrance industry, where it is used to enhance the sensory experience of food products and perfumes. In particular, it is found in various food items such as roasted nuts, coffee, and certain cooked foods, contributing to their overall flavor profile. The compound's ability to impart a desirable aroma makes it a sought-after ingredient in the formulation of food flavorings and fragrance compositions.

In addition to its applications in the flavor and fragrance industries, 2-secbutylpyrazine has been explored for its potential use in agrochemicals. Research indicates that certain pyrazine derivatives exhibit insect-repellent properties, suggesting that 2-secbutylpyrazine may have applications in pest control formulations. The compound's structural characteristics allow for the modification of its properties, enabling the development of more effective and environmentally friendly insect repellents.

Safety and regulatory considerations are important when utilizing 2-secbutylpyrazine in various applications. The compound is generally recognized as safe (GRAS) when used in food flavoring at approved concentrations. However, as with many chemical substances, proper handling and safety precautions are essential to minimize exposure risks. Manufacturers and formulators must adhere to guidelines established by regulatory agencies to ensure consumer safety.

Research continues to explore the broader implications of 2-secbutylpyrazine in various fields. Investigations into its sensory properties and potential benefits in other applications, such as pharmaceuticals and cosmetic formulations, are ongoing. As the demand for natural and synthetic flavors and fragrances increases, the significance of compounds like 2-secbutylpyrazine is expected to grow.

In conclusion, 2-secbutylpyrazine is a notable compound with diverse applications in flavoring, fragrance, and potentially agrochemical formulations. Its discovery and development highlight the importance of pyrazine derivatives in enhancing sensory experiences in food and cosmetics. As research advances, the potential applications of 2-secbutylpyrazine may continue to expand, underscoring its relevance in modern chemistry and industry.