121594-49-8

Basic information

• Product Name: 2,5-dibromo-3,6-dimethyl-pyrazine
• Synonyms: 2,5-Dibromo-3,6-dimethylpyrazine; pyrazine, 2,5-dibromo-3,6-dimethyl-
• CAS NO: 121594-49-8
• Molecular Formula: C₆H₆Br₂N₂
• Molecular Weight: 265.9332
• Mol File: 121594-49-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 255.533°C at 760 mmHg
• Flash Point: 108.343°C
• Density: 1.889g/cm³
• Vapor Pressure: 0.026mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2,5-dibromo-3,6-dimethyl-pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dibromo-3,6-dimethyl-pyrazine(121594-49-8)
• EPA Substance Registry System: 2,5-dibromo-3,6-dimethyl-pyrazine(121594-49-8)

Safety Data

• Hazardous Substances Data: 121594-49-8(Hazardous Substances Data)

Usage

General Description

2,5-dibromo-3,6-dimethyl-pyrazine is a chemical compound that belongs to the pyrazine family, which are commonly used in the food and fragrance industry. It is a yellowish liquid with a strong odor and is known for its role in adding a roasted, nutty, and caramel-like flavor to various food products. 2,5-dibromo-3,6-dimethyl-pyrazine is also used in the manufacturing of pharmaceuticals, dyes, and insecticides due to its aromatic and versatile properties. Additionally, it is considered to be a potentially hazardous substance and should be handled with care due to its flammability and irritant properties.

Upstream product

• 5625-46-7 cyclo(-DL-Ala-DL-Ala-) 
• 27023-19-4 2,5-dichloro-3,6-dimethylpyrazine 

Downstream Products

• 109192-11-2 2,5-dimethyl-3,6-bis(phenylethynyl)pyrazine 
• 772160-23-3 2,5-diethynyl-3,6-dimethylpyrazine 

Relevant articles and documents

2,5-Di(aryleneethynyl)pyrazine derivatives: Synthesis, structural and optoelectronic properties, and light-emitting device

A series of 2,5-di(aryleneethynyl)pyrazine derivatives has been synthesised in 23-41% yields by two-fold reaction of 2,5-dibromo-3,6-dimethylpyrazine 3 with ethynylarenes (arene = phenyl, 2-pyridyl, 4-ethylphenyl, 4-chlorophenyl, 4-biphenyl) under standard Sonogashira conditions [CuI, Pd(PPh3) 2CI2, NEt3, THF]. Compound 3 has been converted into 2,5-diethynyl-3,6-dimethylpyrazine, which reacts with 2-iodothiophene to yield 2,5-bis(thien-2-ylethynyl)-3,6-dimethylpyrazine. In the X-ray crystal structure of 2,5-di(phenylethynyl)-3,6-dimethylpyrazine 4 the two phenyl rings are parallel and the pyrazine ring is inclined to their planes by 14.2°. Quantum chemical calculations establish that the HOMO-LUMO gap for 4 (3.56 eV) is lower than that of di(phenylethynyl)benzene 12 (3.72 eV). The nitrogen atoms of 4 serve to localise the HOMO on the central ring's carbon atoms, resulting in a quinoidal-type population, in contrast to 12. Cyclic voltammetric studies establish that 4 undergoes a reduction to the radical anion at ca. -1.9 V (vs. Ag/Ag+ in MeCN), which is almost reversible at high scan rates (500 mV s-1). The UV-vis absorption and photoluminescence profiles of 4 in cyclohexane are similar to those of 12; the emission for 4 (λ max 379 and 395 nm) is red-shifted compared to 12. Single-layer OLEDs using MEH-PPV as the emissive polymer show significantly enhanced external quantum efficiencies (up to 0.07%) when 20% by weight of 2,5-di(biphenyl-4- ethynyl)-3,6-dimethylpyrazine 8 is added as a dopant: this is ascribed to the enhanced electron-transporting properties of the pyrazine system.