3-Bromo-2-butanone
[CAS# 814-75-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: 3-Bromo-2-butanone
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151.00
• CAS Registry Number: 814-75-5
• EC Number: 212-404-6
• SMILES: CC(C(=O)C)Br

Properties

• Density: 1.416
• Refractive index: 1.460
• Boiling point: 69-70 °C (70 mmHg)
• Flash point: 51 °C

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H302-H312-H314
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

3-Bromo-2-butanone is an organic compound with the molecular formula C4H7BrO. It is a halogenated ketone, characterized by the presence of a bromine atom attached to the second carbon of a butanone chain. This compound is notable for its reactivity and has been explored in various chemical syntheses and applications, particularly in organic chemistry.

The discovery of 3-Bromo-2-butanone is linked to the broader exploration of halogenated ketones, which are valuable intermediates in organic synthesis due to their electrophilic nature. The bromine atom in 3-Bromo-2-butanone increases the electrophilicity of the carbonyl carbon, making it more reactive towards nucleophiles. This reactivity has made the compound an important building block in the synthesis of more complex molecules.

One of the primary applications of 3-Bromo-2-butanone is in the synthesis of pharmaceuticals. The compound’s reactive carbonyl group can undergo nucleophilic addition reactions, which are crucial in forming carbon-carbon and carbon-heteroatom bonds. These reactions are foundational in constructing the backbone of various organic molecules, including drug candidates. 3-Bromo-2-butanone can be used to introduce brominated functionality into molecules, which can then be further modified or used as intermediates in the synthesis of bioactive compounds.

In addition to its role in pharmaceutical synthesis, 3-Bromo-2-butanone is also used in the preparation of heterocyclic compounds. Heterocycles, which contain atoms of at least two different elements as members of their rings, are common structural motifs in many natural products and drugs. The reactivity of 3-Bromo-2-butanone makes it suitable for constructing such rings, particularly those containing nitrogen or oxygen atoms. These heterocyclic compounds are often explored for their potential therapeutic properties, including antibacterial, antifungal, and anticancer activities.

Another important application of 3-Bromo-2-butanone is in the field of polymer chemistry. It can be used as a monomer or a modifying agent in the synthesis of specialty polymers. The bromine atom in the compound can participate in substitution reactions, allowing for the introduction of various functional groups into the polymer chain. This ability to modify the polymer structure can lead to the development of materials with specific properties, such as enhanced thermal stability, chemical resistance, or mechanical strength. These modified polymers can be used in a wide range of applications, from coatings and adhesives to advanced materials in electronics and aerospace industries.

Furthermore, 3-Bromo-2-butanone is also utilized in the agrochemical industry. Halogenated ketones like 3-Bromo-2-butanone can be used to synthesize pesticides and herbicides, where the bromine atom can enhance the biological activity of the final product. These agrochemicals are essential in protecting crops from pests and diseases, contributing to improved agricultural productivity.

The compound’s reactivity is not without challenges, as handling and storage require caution due to its potential to undergo unwanted reactions under certain conditions. Nonetheless, the versatility of 3-Bromo-2-butanone in organic synthesis makes it a valuable tool for chemists, enabling the construction of complex molecules and the development of new materials.

In summary, 3-Bromo-2-butanone is a reactive and versatile compound with significant applications in pharmaceuticals, polymer chemistry, and agrochemicals. Its discovery and development have contributed to advancements in organic synthesis, enabling the creation of a wide range of valuable chemical products.

References

2005. Use of a Metallation Reaction to Obtain Substituted 2-(5-Methyl-2-thiazolyl)ethanols. Chemistry of Heterocyclic Compounds, 41(7).
DOI: 10.1007/s10593-005-0242-0

2008. One-Pot Synthesis of Imidazopyridine Derivatives. Synthesis, 2008(5).
DOI: 10.1055/s-2007-1000936

2016. N,N-Dibromo-p-Toluenesulfonamide (TsNBr2): A Promising Alternative Bromo-Organic Reagent. Synlett, 27(7).
DOI: 10.1055/s-0035-1562024