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Merck
CN

230995

2-(2-Bromoethyl)-1,3-dioxolane

96%

Synonym(s):

3-Bromopropionaldehyde ethylene acetal

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About This Item

Empirical Formula (Hill Notation):
C5H9BrO2
CAS Number:
18742-02-4
Molecular Weight:
181.03
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24853846
EC Number:
242-551-1
Beilstein/REAXYS Number:
103516
MDL number:
MFCD00003216

Key Documents

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Product Name

2-(2-Bromoethyl)-1,3-dioxolane, 96%

InChI key

GGZQLTVZPOGLCC-UHFFFAOYSA-N

InChI

1S/C5H9BrO2/c6-2-1-5-7-3-4-8-5/h5H,1-4H2

SMILES string

BrCCC1OCCO1

assay

96%

form

liquid

contains

sodium bicarbonate as stabilizer

refractive index

n20/D 1.479 (lit.)

bp

68-70 °C/8 mmHg (lit.)

density

1.542 g/mL at 25 °C (lit.)

functional group

bromo
ether

storage temp.

2-8°C

Quality Level

200

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Application

2-(2-Bromoethyl)-1,3-dioxolane was used:
  • as starting reagent for the synthesis of (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid and (5Z,9Z)-5,9-eicosadienoic acid
  • in synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine
  • in asymmetric total synthesis of both enantiomers of marine mollusk metabolite pulo′upone via Evans′ asymmetric Diels-Alder reaction
  • as alkylating agent for amines, dithianes and carboximides
  • with eynamides and sodium azide in a "one-pot" synthesis of triazoles

General description

Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride affords the key organotrifluoroborate reagent.

2-(2-Bromoethyl)-1,3-dioxolane is a cyclic ether derivative with a dioxolane ring, used as a building block in organic synthesis and polymer industry.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

149.0 °F - closed cup

flash_point_c

65 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7932V
WXBF5679V
WXBF2937V
WXBF4315V
WXBF3114V

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New method for the synthesis of formaldehyde-free phenolic resins from lignin-based aldehyde precursors
Foyer G, et al.
European Polymer Journal, 74, 296-309 (2016)
Journal of the Chemical Society. Perkin Transactions 1, 15-15 (1994)
Advanced Synthesis & Catalysis, 348, 2437-2437 (2006)
Nicolas Fleury-Brégeot et al.
Organic letters, 15(7), 1536-1539 (2013-03-16)
A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides
Journal of the Chemical Society. Perkin Transactions 1, 681-681 (1993)
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