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Benzyl 2-bromoethyl ether

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CAS:1462-37-9
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  • CAS:1462-37-9
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Benzyl 2-bromoethyl ether Basic information
Product Name:Benzyl 2-bromoethyl ether
Synonyms:BENZYL 2-BROMOETHYL ETHER;1-BROMO-2-BENZYLOXYETHANE;1-BENZYLOXY-2-BROMOETHANE;2-BENZYLOXY-1-BROMOETHANE;Benzyl 2-bromoethyl ether, 97 % (GC);(2-Bromoethoxymethyl)benzene;Benzyloxyethyl Bromide;Benzene, [(2-broMoethoxy)Methyl]-
CAS:1462-37-9
MF:C9H11BrO
MW:215.09
EINECS:629-202-2
Product Categories:alkyl bromide;Building Blocks;C9;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Ethers;Organic Building Blocks;Oxygen Compounds;1462-37-9
Mol File:1462-37-9.mol
Benzyl 2-bromoethyl ether Structure
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.)
Fp >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
InChIInChI=1S/C9H11BrO/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5H,6-8H2
InChIKeyFWOHDAGPWDEWIB-UHFFFAOYSA-N
SMILESC1(COCCBr)=CC=CC=C1
CAS DataBase Reference1462-37-9
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 24/25
RIDADR UN 3334
WGK Germany 3
TSCA No
HS Code 29093090
Storage Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
ProviderLanguage
SigmaAldrich English
Benzyl 2-bromoethyl ether Usage And Synthesis
Chemical PropertiesClear colorless to pale yellow liquid
UsesBenzyl 2-broMoethyl ether is a reactant used in the preparation of muscarinic antagonist.
UsesAlkylation reagent for synthesis of a macrocyclic antifungal antibiotic. Building block used to prepare a copper phthalocyanine discotic liquid crystal.
General DescriptionBenzyl 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
2-Benzyloxyethanol

622-08-2

Benzyl 2-bromoethyl ether

1462-37-9

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).

ReferencesMartin 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 Preparation Products And Raw materials
Raw materialsCarbon tetrabromide-->2-Benzyloxyethanol-->Dichloromethane-->Triphenylphosphine-->N-Bromosuccinimide
Preparation Products1-[2-(benzyloxy)ethyl]tetrahydro-4(1H)-pyridinone
Tag:Benzyl 2-bromoethyl ether(1462-37-9) Related Product Information
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