2-Bromo-1-(4-chlorophenyl)propan-1-one
[CAS# 877-37-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 2-Bromo-1-(4-chlorophenyl)propan-1-one
• Molecular Formula: C₉H₈BrClO
• Molecular Weight: 247.52
• CAS Registry Number: 877-37-2
• EC Number: 814-935-4
• SMILES: CC(C(=O)C1=CC=C(C=C1)Cl)Br

Properties

• Solubility: 57.28 mg/L (25 ºC water)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.570, Calc.^*
• Melting point: 66.98 ºC
• Boiling Point: 284.29 ºC, 296.7±15.0 ºC (760 mmHg), Calc.^*
• Flash Point: 133.2±20.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H314
• Precautionary Statements: P261-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Bromo-1-(4-chlorophenyl)propan-1-one, also known as 4-chloro-α-bromo-phenylacetone, is an organic compound commonly used in organic synthesis, particularly in the preparation of various pharmaceutical and chemical intermediates. This compound contains both a bromine atom at the α-position (relative to the carbonyl group) and a chlorophenyl group attached to the carbonyl carbon. The structure of 2-bromo-1-(4-chlorophenyl)propan-1-one makes it a valuable intermediate in the synthesis of compounds used in medicinal chemistry and the development of agrochemicals.

The compound is typically synthesized through an electrophilic substitution reaction, where the bromine atom is introduced at the α-position of phenylacetone derivatives. The synthesis involves the reaction of a 4-chloro phenyl compound with a suitable brominating agent, followed by carbonylation to form the final product. The 4-chlorophenyl group plays an important role in the electronic properties of the compound, often enhancing its reactivity in certain reactions and making it suitable for further functionalization.

The use of 2-bromo-1-(4-chlorophenyl)propan-1-one extends to the synthesis of various bioactive compounds. For instance, it is used as a precursor for the preparation of substituted amphetamines and other psychoactive substances, where the halogenated aromatic ring helps to modulate the pharmacological activity of the final product. Additionally, derivatives of 2-bromo-1-(4-chlorophenyl)propan-1-one may exhibit antimicrobial, anti-inflammatory, and other therapeutic properties, which have made it a compound of interest in the development of new pharmaceutical agents.

Despite its potential applications in pharmaceutical chemistry, it is important to note that compounds like 2-bromo-1-(4-chlorophenyl)propan-1-one are highly regulated due to their potential use in the illicit production of controlled substances. As such, any synthesis or handling of this compound must adhere to the appropriate legal and safety regulations.

In summary, 2-bromo-1-(4-chlorophenyl)propan-1-one is an important intermediate in organic synthesis, particularly in the field of medicinal chemistry. Its use in the preparation of various bioactive compounds, especially those with potential therapeutic effects, underscores its significance in the development of new drugs. However, its regulation and handling should be carefully managed due to its potential misuse in the synthesis of controlled substances.

References

2016. Spectroscopic characterization and crystal structures of two cathinone derivatives: N-ethyl-2-amino-1-phenylpropan-1-one (ethcathinone) hydrochloride and N-ethyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-CEC) hydrochloride. Forensic Toxicology, 35(1).
DOI: 10.1007/s11419-016-0345-6

2002. Ring Closure Including Ring Transformation. Science of Synthesis