1-Bromo-2-butyne
[CAS# 3355-28-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Bromo-2-butyne
• Molecular Formula: C₄H₅Br
• Molecular Weight: 132.99
• CAS Registry Number: 3355-28-0
• EC Number: 608-891-3
• SMILES: CC#CCBr

Properties

• Density: 1.519
• Boiling point: 40-41 °C (20 mmHg)
• Refractive index: 1.508
• Flash point: 36 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301

• Transport Information: UN 1993

Discovery and Applications

1-Bromo-2-butyne is a versatile chemical compound with significant implications in both organic synthesis and industrial applications. This substance, with the molecular formula C4H5Br, is known for its unique structural features, including a triple bond and a bromine atom attached to a butyne backbone.

The discovery of 1-Bromo-2-butyne can be traced back to the field of organic chemistry, where researchers have continually explored ways to synthesize and utilize compounds with triple bonds. The synthesis of 1-Bromo-2-butyne generally involves the bromination of 2-butyne, a process that introduces a bromine atom to the alkyne group. This reaction is typically carried out using bromine in a suitable solvent, resulting in the formation of 1-Bromo-2-butyne.

One of the notable features of 1-Bromo-2-butyne is its reactivity due to the presence of both a triple bond and a bromine atom. The triple bond in the molecule makes it an excellent candidate for further chemical transformations, including addition reactions and polymerization processes. The bromine atom, being a good leaving group, enhances the compound's utility in various substitution reactions.

In organic synthesis, 1-Bromo-2-butyne serves as an essential building block for the construction of more complex molecules. Its reactivity allows it to participate in a range of chemical reactions, such as cross-coupling reactions, which are crucial for forming carbon-carbon bonds. For example, it can be used in Suzuki or Stille coupling reactions to create more intricate organic structures. This makes it valuable in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

The compound's applications extend beyond synthetic chemistry into industrial processes. 1-Bromo-2-butyne is employed in the preparation of various polymers and materials. Its ability to act as a monomer in polymerization reactions allows for the creation of polymers with unique properties, such as enhanced strength or flexibility. Additionally, it is used in the manufacture of fine chemicals and as an intermediate in the production of other brominated compounds.

In the field of materials science, 1-Bromo-2-butyne is utilized in the development of functionalized materials. Its reactivity can be harnessed to modify surfaces or create materials with specific chemical properties. This includes applications in coatings, adhesives, and other industrial products where its presence can impart desired characteristics.

Furthermore, 1-Bromo-2-butyne has potential uses in the pharmaceutical industry. Its ability to form stable and reactive intermediates makes it a valuable tool in the synthesis of complex drug molecules. Researchers explore its application in creating new pharmaceuticals with improved efficacy and safety profiles. The compound's role in drug discovery and development highlights its importance in advancing medicinal chemistry.

In conclusion, 1-Bromo-2-butyne is a significant compound in both organic synthesis and industrial applications. Its unique structure and reactivity make it a valuable building block for creating more complex molecules and materials. Its applications span across synthetic chemistry, materials science, and pharmaceuticals, showcasing its versatility and importance in various fields.

References

2023. Synthesis of Polyfunctionalized Conjugated 1,3-Enynes. Synlett, 34(16).
DOI: 10.1055/s-0042-1751510

2022. Synthesis of Chiral Propargyl Alcohols. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-00607