2-Bromo-4'-methylpropiophenone
[CAS# 1451-82-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 2-Bromo-4'-methylpropiophenone
• Synonyms: 2-Bromo-1-(4-methylphenyl)-1-propanone
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.10
• CAS Registry Number: 1451-82-7
• EC Number: 696-162-0
• SMILES: CC1=CC=C(C=C1)C(=O)C(C)Br

Properties

• Density: 1.357
• Melting point: 75-77 °C
• Boiling point: 273 °C
• Flash point: 59 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Bromo-4'-methylpropiophenone, also known as BMK, was discovered through organic synthesis efforts aimed at developing novel chemical compounds with diverse applications. Its discovery likely occurred in the context of exploring substituted propiophenones and their derivatives for potential uses in pharmaceuticals, agrochemicals, and materials science. The synthesis of BMK involved the bromination of 4'-methylpropiophenone, resulting in the introduction of a bromine atom at the 2-position of the phenyl ring.

BMK serves as a valuable intermediate in the synthesis of various organic compounds. Its chemical reactivity allows for the introduction of functional groups and structural modifications, enabling the preparation of complex molecules and fine chemicals used in pharmaceuticals, agrochemicals, and specialty chemicals.

BMK and its derivatives find applications in pharmaceutical synthesis as building blocks for the preparation of drug compounds. Pharmaceutical researchers utilize BMK-derived intermediates to introduce specific functional groups and stereochemistry required for the development of drug candidates targeting a wide range of therapeutic areas.

BMK serves as a versatile reagent in organic synthesis, participating in various reactions such as acylation, alkylation, and cyclization. Its diverse chemical transformations enable the synthesis of biologically active compounds, natural products, and functional materials.

BMK derivatives are used in the synthesis of agrochemicals such as insecticides, herbicides, and fungicides. These compounds play a crucial role in pest management and crop protection.

BMK and its derivatives are valuable tools in chemical research and development. Researchers utilize BMK-based compounds to explore new synthetic methodologies, develop novel chemical transformations, and investigate structure-activity relationships in drug discovery and materials science.

BMK is of interest in forensic science due to its potential involvement in the illicit synthesis of controlled substances such as amphetamines and synthetic drugs. Forensic laboratories may use analytical techniques to detect and quantify BMK in seized drug samples, aiding in drug enforcement efforts and criminal investigations.

References

2023. Double C-H bond functionalization for C-C coupling at the β-position of thiophenes using palladium-catalyzed 1,4-migration associated with direct arylation. Org. Chem. Front., 10(6).
DOI: 10.1039/D3QO00018D

2016. 1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water. Org. Biomol. Chem., 14(48).
DOI: 10.1039/C6OB02200F

2014. Pd-catalyzed tandem homocoupling-aldol-dehydration of ortho-acylphenyl iodides. RSC Adv., 4(45).
DOI: 10.1039/C4RA02055C