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230995

Sigma-Aldrich

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:
Molecular Weight:
181.03
Beilstein:
103516
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

SMILES string

BrCCC1OCCO1

InChI

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

InChI key

GGZQLTVZPOGLCC-UHFFFAOYSA-N

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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.

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

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

230995-10G:
230995-BULK:
230995-VAR:
230995-50G:


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Journal of the Chemical Society. Perkin Transactions 1, 15-15 (1994)
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
Advanced Synthesis & Catalysis, 348, 2437-2437 (2006)
Journal of the Chemical Society. Perkin Transactions 1, 681-681 (1993)
A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-< i> epi</i>-castanospermine.
Patil NT, et al.
Tetrahedron Letters, 42(4), 747-749 (2001)

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