📰 Benzyl 2-bromoethyl ether (CAS 1462-37-9): A Bromo-Functional Benzyl Ether Intermediate for Organic Synthesis

September 23, 2026

1、Product Overview

Benzyl 2-bromoethyl ether, Chinese name 苄基2-溴乙基醚, also known as 2-(benzyloxy)ethyl bromide, is a bifunctional organic intermediate containing a benzyl-protected ether moiety and a primary alkyl bromide. The molecule combines a benzyl ether group with a reactive bromoethyl chain, giving it useful functionality for nucleophilic substitution, alkylation and protecting-group strategies in organic synthesis.

The molecular formula of Benzyl 2-bromoethyl ether is C₉H₁₁BrO, with a molecular weight of 215.09 g/mol. Its CAS number is 1462-37-9. Commercial material is typically supplied as a colorless to light yellow liquid.

Because of its reactive bromide terminus, Benzyl 2-bromoethyl ether can be used to introduce a 2-(benzyloxy)ethyl group into target molecules. The benzyl ether portion can also serve as a protected alcohol equivalent and can be removed under appropriate deprotection conditions, such as hydrogenolysis. These features make it relevant to pharmaceutical intermediates, agrochemical synthesis, functional materials and specialty chemical development.

2、Basic Product Information

1）Product Name: Benzyl 2-bromoethyl ether

2）Chinese Name: 苄基2-溴乙基醚

3）CAS NO.: 1462-37-9

4）Synonyms: 2-(Benzyloxy)ethyl bromide; 2-Bromoethyl benzyl ether; 1-Bromo-2-(benzyloxy)ethane; (2-Bromoethoxy)methylbenzene; 2-溴乙基苄基醚; 2-(苄氧基)乙基溴

5）Molecular Formula: C₉H₁₁BrO

6）Molecular Weight: 215.09 g/mol

7）Structural Formula:

8）Purity: Typically ≥97% (GC); customized purity available upon request

9）Moisture Content: Customizable upon request

10）Appearance: Colorless to light yellow liquid

11）Physical State: Liquid at room temperature

12）Boiling Point: Approximately 140–142 °C at reduced pressure; literature values may vary

13）Product Manager Email: Echo@coreychem.com

3、Frequently Asked Questions (FAQ)

4、Application Cases

1）Use as a Two-Carbon Linker to Introduce a 2-(Benzyloxy)ethyl Fragment

Benzyl 2-bromoethyl ether is a bifunctional C2 intermediate. Its bromide terminus can react with suitable nucleophiles to introduce a 2-(benzyloxy)ethyl fragment (—CH₂CH₂OBn) into a target molecule. This fragment contains a benzyl-protected oxygen functionality, making it useful for multi-step synthesis where a two-carbon chain and a hydroxyl precursor are required. After deprotection, the corresponding hydroxyethyl derivative can be obtained.

2）Nucleophilic Substitution at the Primary Bromide with Non-Amine Nucleophiles

The primary carbon–bromine bond can undergo nucleophilic substitution. Reactions with thiols or thiolates, alkoxides, azides, cyanides, carboxylates, and related nucleophiles can provide thioethers, ethers, azides, nitriles, esters, and other derivatives. Reaction conditions should be optimized according to the nucleophile, solvent, base, and temperature. Under strongly basic conditions, elimination may compete with substitution.

3）N-Alkylation of Amines and Nitrogen-Containing Heterocycles

Benzyl 2-bromoethyl ether can serve as an alkylating reagent for primary and secondary amines and for N—H-containing heterocycles such as imidazoles, pyrazoles, triazoles, benzimidazoles, indoles, and carbazoles. The reaction introduces a 2-(benzyloxy)ethyl substituent, which can be converted to a hydroxyethyl group after deprotection. With amines, over-alkylation should be considered and can be minimized by controlling the molar ratio, addition rate, temperature, base, and solvent.

4）Benzyl Ether as a Protected Oxygen Functionality in Multi-Step Synthesis

The benzyl ether moiety serves as a protected oxygen functionality. It is generally stable under many basic, nucleophilic, and mildly acidic conditions, allowing transformations at the bromide terminus while retaining the oxygen functionality. The benzyl group can subsequently be removed, for example by catalytic hydrogenolysis, to release the alcohol. Deprotection conditions should be selected with consideration of other functional groups, such as azides, alkenes, and halides.

5）Synthesis of Functionalized Hydroxyethyl Intermediates

By combining nucleophilic substitution at the bromoethyl site with subsequent benzyl deprotection, Benzyl 2-bromoethyl ether can be used to prepare various functionalized hydroxyethyl compounds, including amino alcohols, thioether alcohols, azido alcohols, and hydroxyethyl heterocycles. These intermediates can be useful in medicinal chemistry, ligand synthesis, and functional organic molecule development where a two-carbon chain is required and the oxygen functionality must be temporarily protected. The substitution and deprotection sequence can be designed according to the target structure.

5、Safety and Storage

1）Store in a tightly closed container in a cool, dry and well-ventilated area.

2）Keep the material away from excessive moisture, heat, direct sunlight and incompatible chemicals.

3）Because the product is a liquid, handle it in a well-ventilated area and avoid inhalation of vapors.

4）Use appropriate personal protective equipment, including chemical-resistant gloves, safety glasses or goggles and protective clothing.

5）Avoid contact with eyes, skin and clothing. Wash thoroughly after handling.

6）Keep away from sources of ignition. Consult the supplier’s current SDS and technical specification for detailed handling, personal-protection, storage and transportation requirements.