3-Amino-6-bromopyrazine-2-carbonitrile
[CAS# 17231-51-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 3-Amino-6-bromopyrazine-2-carbonitrile
• Molecular Formula: C₅H₃BrN₄
• Molecular Weight: 199.01
• CAS Registry Number: 17231-51-5
• EC Number: 803-348-9
• SMILES: C1=C(N=C(C(=N1)N)C#N)Br

Properties

• Density: 1.9±0.1 g/cm³ Calc.^*
• Boiling point: 341.0±42.0 °C 760 mmHg (Calc.)^*
• Flash point: 160.0±27.9 °C (Calc.)^*
• Index of refraction: 1.67 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H318
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P354+P338-P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

3‑Amino‑6‑bromopyrazine‑2‑carbonitrile is a heterocyclic organic compound with the molecular formula C₅H₃BrN₄ and CAS number 17231‑51‑5. It contains a pyrazine ring substituted with an amino group at the 3‑position, a bromine atom at the 6‑position, and a nitrile (–C≡N) moiety at the 2‑position. The compound is typically obtained as a yellow crystalline solid.

Because of its substituents, this molecule is useful in synthetic organic chemistry. The bromine atom offers a site for cross‑coupling reactions (e.g., Suzuki, Sonogashira), which enables introduction of various aryl or alkenyl groups at the 6‑position. The nitrile group is also synthetically versatile: it can undergo transformations to amines, amidines, heterocycles, or serve as a functional group in further derivatization.

In terms of synthesis, a plausible route involves starting from 3‑aminopyrazine‑2‑carbonitrile, followed by regioselective bromination at the 6‑position. Literature reported in chemical‑supplier databases suggests the use of N‑bromosuccinimide (NBS) for bromination. Alternative synthetic strategies could involve creating the 3‑aminopyrazine core first, then introducing the nitrile group and the bromine substituent through appropriate functional group interconversions.

Applications of 3‑Amino‑6‑bromopyrazine‑2‑carbonitrile are mainly as a building block in medicinal and agrochemical chemistry. Because the aminopyrazine motif is found in many bioactive molecules, this compound can serve as a privileged scaffold. Derivatives of this core have potential as kinase inhibitors, antimicrobial agents, or other small‑molecule modulators.

In practical laboratory usage, the compound is handled under standard conditions for brominated heterocycles: anhydrous solvents, inert atmosphere, and drying to avoid hydrolysis or side reactions. According to chemical catalogue data, it has a melting point around 183‑184 °C.

Currently, there are no notable peer‑reviewed publications that focus exclusively on the discovery, detailed biological properties, or therapeutic applications of this exact molecule. Its use remains primarily as an intermediate in synthetic chemistry rather than as a final active pharmaceutical ingredient.