alpha-Bromovalerophenone
[CAS# 49851-31-2]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: alpha-Bromovalerophenone
• Synonyms: 2-Bromo-1-phenyl-1-pentanone; 2-Bromo-1-phenylpentan-1-one; 2-Bromovalerophenone
• Molecular Formula: C₁₁H₁₃BrO
• Molecular Weight: 241.12
• CAS Registry Number: 49851-31-2
• SMILES: CCCC(C(=O)C1=CC=CC=C1)Br

Properties

• Solubility: Practically insoluble (0.087 g/L) (25 °C), Calc.^*
• Density: 1.310±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 159 °C (22 Torr)^**
• Flash point: 42.5±7.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

^** GB 927475 1963.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Alpha-Bromovalerophenone is an organic compound first synthesized in the early 20th century as part of efforts to explore new chemical entities with potential industrial and pharmaceutical applications. This compound is characterized by a bromine atom attached to the alpha position of a valerophenone molecule. Its discovery was driven by the need to develop intermediates for various chemical reactions and processes, providing a versatile building block for further chemical synthesis.

Alpha-Bromovalerophenone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its structure allows it to participate in multiple chemical reactions, making it a valuable precursor in the creation of drugs. It is particularly useful in synthesizing compounds with sedative, anticonvulsant, and analgesic properties. Researchers exploit its reactive bromine atom to introduce different functional groups, enhancing the pharmacological activity of the resulting drugs.

In the field of chemical research, alpha-Bromovalerophenone serves as a critical reagent for studying reaction mechanisms and developing new synthetic methodologies. Its reactivity with nucleophiles and its ability to undergo substitution reactions make it an excellent model compound for educational and experimental purposes. Chemists utilize it to explore new reaction pathways and optimize existing synthetic routes, contributing to advancements in organic chemistry.

Alpha-Bromovalerophenone is also used in the synthesis of agrochemicals, including herbicides and insecticides. Its role as an intermediate enables the production of compounds that protect crops from pests and diseases, improving agricultural productivity. By serving as a precursor for active ingredients in these agrochemicals, it helps ensure the health and growth of crops, contributing to food security.

Beyond its role in pharmaceuticals and agriculture, alpha-Bromovalerophenone finds applications in various industrial processes. It is used in the manufacture of specialty chemicals, such as dyes and fragrances. Its chemical properties allow it to be transformed into compounds that impart desired characteristics to consumer products, enhancing their functionality and appeal.

In material science, alpha-Bromovalerophenone is utilized to develop new polymers and materials with unique properties. Its ability to act as a cross-linking agent and participate in polymerization reactions makes it valuable in creating advanced materials with specific mechanical, thermal, and chemical properties. These materials find applications in coatings, adhesives, and other high-performance products.

References

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2008. Polymer-Supported Synthesis of α- and β-Hydroxyketones through the Formation of 1,3-Dithiane Intermediates. Synlett, 2008(8).
DOI: 10.1055/s-2008-1072738

2013. Metabolism of the newly encountered designer drug α-pyrrolidinovalerophenone in humans: identification and quantitation of urinary metabolites. Forensic Toxicology, 32(1).
DOI: 10.1007/s11419-013-0202-9