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Sigma-Aldrich

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

96%

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Synonym(s):
3-Bromopropionaldehyde ethylene acetal
Empirical Formula (Hill Notation):
C5H9BrO2
CAS Number:
18742-02-4
Molecular Weight:
181.03
Beilstein:
103516
EC Number:
242-551-1
MDL number:
MFCD00003216
PubChem Substance ID:
24853846
NACRES:
NA.22

Quality Level

200

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.)

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
GHS06

Signal Word

Danger

Hazard Statements

H301 - H315 - H319 - H335

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

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Journal of the Chemical Society. Perkin Transactions 1, 681-681 (1993)
N M Carballeira et al.
Chemistry and physics of lipids, 100(1-2), 33-40 (2000-01-20)
The delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and
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)
Asymmetric total syntheses of (+)-and (-)-pulo'upone.
Sugahara T, et al.
Tetrahedron Letters, 30(!4), 1821-1824 (1989)
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
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