Benzyl 2-bromoethyl ether Chemical Properties

Boiling point:

254 °C(lit.)

Density 

1.36 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.541(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

liquid

color 

colorless to yellow

Water Solubility 

Slightly soluble in water

InChI

InChI=1S/C9H11BrO/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5H,6-8H2

InChIKey

FWOHDAGPWDEWIB-UHFFFAOYSA-N

SMILES

C1(COCCBr)=CC=CC=C1

CAS DataBase Reference

1462-37-9

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

RIDADR 

UN 3334

WGK Germany 

3

TSCA 

No

HS Code 

29093090

MSDS

• Language:English Provider:SigmaAldrich

Benzyl 2-bromoethyl ether Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Benzyl 2-broMoethyl ether is a reactant used in the preparation of muscarinic antagonist.

Uses

Alkylation reagent for synthesis of a macrocyclic antifungal antibiotic. Building block used to prepare a copper phthalocyanine discotic liquid crystal.

General Description

Benzyl 2-bromoethyl ether is an organic building block. Its enthalpy of vaporization at boiling point (527.15K) has been reported to be 46.499kjoule/mol.

Synthesis

Step 2: To a stirred solution of 2-benzyloxyethanol (17.0 g, 111.884 mmol) and triphenylphosphine (35.0 g, 134.21 mmol) in dichloromethane (170 mL) was slowly added N-bromosuccinimide (23.88 g, 134.21 mmol) in batches at a temperature between -10°C and -5°C, keeping the reaction temperature at -10 °C to -5 °C. After the addition was completed, the reaction mixture was continued to be stirred at room temperature for 1 hour until complete consumption of the feedstock was confirmed by thin layer chromatography (TLC) analysis. Upon completion of the reaction, the mixture was concentrated and the crude product was purified by column chromatography (CC) using a petroleum ether solution of 5% ethyl acetate as eluent to afford benzyl 2-bromoethyl ether (13.5 g, 56.2% yield) as a light yellow liquid (TLC conditions: petroleum ether solution of 30% ethyl acetate; Rf value: 0.7).

References

Martin W. M. Fijten.; Claudia Haensch.; Bart M. van Lankvelt.; Richard Hoogenboom.; Ulrich S. Schubert. Clickable Poly(2-Oxazoline)s as Versatile Building Blocks. Macromolecular Chemistry and Physics. 2008, 209 (18),1887-1895. DOI:10.1002/MACP.200800226
Britt A. Minch.; Wei Xia.; Carrie L. Donley.; Ryan M. Hernandez.; Chet Carter.; Michael D. Carducci.; Alice Dawson.; David F. O'Brien.; Neal R. Armstrong. Octakis(2-benzyloxyethylsulfanyl) Copper (II) Phthalocyanine: A New Liquid Crystalline Discotic Material with Benzyl-Terminated, Thioether-Linked Side Chains. Chem. Mater.2005,17 (7),1618-1627. DOI:10.1021/CM0483745
Org. Lett. 5, 4049-4052, (2003) 2. Chem. Mater. 17, 1618, (2005)

Benzyl 2-bromoethyl ether(1462-37-9)Related Product Information

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• 2 3 5-TRI-O-BENZOYL-ALPHA-D-ARABINO-FURA
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• 5,6-DIBROMO-2-(2,4-DICHLOROPHENYL)-1,3-DIOXEPANE