Bromoacetonitrile (CAS 590-17-0), also known as Cyanomethyl Bromide or Bromomethyl Cyanide, is a critical chemical compound widely recognized for its unique reactivity and versatility in organic synthesis. With the molecular formula C2H2BrN and a molecular weight of 119.95 g/mol, this halogenated organic compound presents as a colorless to yellowish liquid, characterized by distinct physical properties that make it invaluable across various industrial and research applications.

Its boiling point typically ranges from 148°C to 150°C, and it possesses a density of approximately 1.7200 g/mL. A flash point exceeding 110°C indicates its handling requires careful consideration. The compound's refractive index, generally between 1.4786 and 1.4806, further defines its optical characteristics. Analytical assays confirm high purity, typically at 96% minimum by GC, ensuring its suitability for demanding synthetic procedures where precise reactions are paramount.

Bromoacetonitrile serves predominantly as a highly effective building block in the chemical industry. Its primary utility lies in its role as an electrophilic reagent due to the presence of both a bromine atom and a nitrile group, facilitating a wide array of chemical transformations. In complex organic synthesis, it is frequently employed in reactions requiring the introduction of a cyanomethyl group. Recent advancements highlight its application in copper-catalyzed atom transfer radical addition reactions (ATRA) with alkenes, enabling the efficient construction of functionalized molecules such as γ-bromonitriles and β,γ-unsaturated nitriles. These reactions are vital for the development of new synthetic pathways for pharmaceutical intermediates, agrochemicals, and specialty chemicals. Furthermore, its reactivity makes it a key precursor for synthesizing a diverse range of heterocyclic compounds, dyes, and other fine chemicals. It is also actively used in academic and industrial research for developing novel chemical processes and discovering new molecular entities.

Due to its chemical nature, Bromoacetonitrile is classified as hazardous. It is toxic if swallowed, in contact with skin, or inhaled, and can cause severe skin burns and eye damage. Proper handling procedures, including the use of personal protective equipment and adequate ventilation, are essential to ensure safety in laboratory and industrial settings.

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