2-Bromo-4'-Benzyloxy-3'-nitroacetophenone
[CAS# 43229-01-2]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 2-Bromo-4'-Benzyloxy-3'-nitroacetophenone
• Synonyms: 2-Bromo-1-[3-nitro-4-(phenylmethoxy)phenyl]-ethanone
• Molecular Formula: C₁₅H₁₂BrNO₄
• Molecular Weight: 350.16
• CAS Registry Number: 43229-01-2
• EC Number: 610-115-3
• SMILES: C1=CC=C(C=C1)COC2=C(C=C(C=C2)C(=O)CBr)[N+](=O)[O-]

Properties

• Melting point: 135-137 °C
• Boiling point: 465.2 °C (760mmHg)

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H315-H318-H319-H335-H370-H400-H410-H412
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P308+P316-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	1	H370
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Bromo-4'-benzyloxy-3'-nitroacetophenone is a compound known for its unique chemical structure. Its discovery stems from a focus on modifying acetophenone derivatives to enhance their reactivity and functional diversity. The goal of the chemists was to introduce bromine and nitro groups to create a molecule with potential uses in pharmaceuticals and materials science. The synthesis involves the bromination of 2,4-dihydroxyacetophenone followed by nitroacetylation. The benzyloxy group introduced via benzyl alcohol helps improve the stability and solubility of the compound, making it a versatile building block in organic synthesis.

2-Bromo-4'-benzyloxy-3'-nitroacetophenone is used in drug development as a key intermediate for the synthesis of bioactive compounds. Its structure allows for modifications that lead to the development of new therapeutic agents with increased efficacy and selectivity. In particular, the nitro group can be converted into a variety of functional groups, facilitating the design of new drugs.

In materials science, this compound is a precursor for the synthesis of functional polymers and organic materials. Its reactivity with different monomers can produce materials with tailored properties, such as enhanced conductivity or optical properties. This versatility is critical for developing advanced materials for electronics, sensors, and coatings.

Researchers use 2-bromo-4'-benzyloxy-3'-nitroacetophenone in synthetic organic chemistry to explore new reaction mechanisms and develop innovative synthetic routes. Its structure allows chemists to study the effects of halogen and nitro groups on reaction outcomes, contributing to a broader understanding of organic synthesis.

References

1994. An intermediate in the synthesis of formoterol. Acta Crystallographica Section C Crystal Structure Communications, 50(4).
DOI: 10.1107/s0108270193009473

2003. Formoterol. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-06-0113

2010. Arformoterol. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0198