4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether
[CAS# 461432-23-5]

Identification

• Classification: Organic raw materials >> Ether compounds and their derivatives
• Name: 4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether
• Synonyms: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
• Molecular Formula: C₁₅H₁₄BrClO
• Molecular Weight: 325.63
• CAS Registry Number: 461432-23-5
• EC Number: 636-921-5
• SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)Br)Cl

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H312-H318-H332-H400-H410
• Safety Statements: P261,

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
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether is a chemical compound with the molecular formula C16H13BrClO. This compound is characterized by its benzyl and phenyl groups, with additional halogen substituents that provide it with unique chemical properties. The synthesis and applications of this compound highlight its importance in various areas of chemical research and development.

The synthesis of 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether generally involves a multi-step procedure. The process typically begins with the preparation of the brominated and chlorinated benzyl group. This can be achieved through halogenation of a suitable precursor, followed by coupling reactions to introduce the phenyl ethyl ether moiety. A common method involves using bromine and chlorine sources to selectively introduce the halogen atoms onto the benzyl ring, followed by the reaction with phenyl ethyl alcohol to form the ether linkage. The final compound is usually purified by techniques such as recrystallization or column chromatography to obtain high-purity material.

In terms of applications, 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether has demonstrated its utility in several areas of chemical research. Its halogenated structure makes it a valuable intermediate in organic synthesis, particularly for the development of more complex molecules. The presence of bromine and chlorine atoms in the molecule introduces specific reactivity patterns that can be exploited in further chemical transformations. For instance, the bromine and chlorine atoms can participate in cross-coupling reactions or serve as functional groups for further derivatization.

One of the notable applications of 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether is in the field of medicinal chemistry. The compound’s structure makes it a useful building block for the synthesis of pharmaceutical agents. The halogen atoms can influence the biological activity of the molecules in which this compound is incorporated. For example, brominated and chlorinated compounds are often studied for their potential anti-cancer, anti-inflammatory, or antimicrobial properties. Researchers can modify the phenyl ethyl ether structure to create derivatives with specific pharmacological activities, making this compound an important tool in drug discovery.

Additionally, 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether is used in materials science and chemical biology. The compound’s unique structure allows for the development of new materials with tailored properties. For instance, the halogenated groups can enhance the compound's ability to interact with other molecules or materials, leading to applications in sensor technology, catalysis, or as a reagent in chemical assays.

In summary, 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether is a compound of significant interest due to its versatile applications in organic synthesis, medicinal chemistry, and materials science. Its halogenated structure provides unique chemical properties that make it a valuable intermediate for the development of more complex and functionalized molecules.

References

2014. Enantiomerically pure synthesis. Chemical Research in Chinese Universities, 30(4).
DOI: 10.1007/s40242-014-3257-1

2014. Preparation of organometallics from functionalized halides. Synthesis, 46(4).
DOI: 10.1055/s-0033-1338567

2017. Dapagliflozin synthesis. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results