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496820

Sigma-Aldrich

4-Vinyl-1,3-dioxolan-2-one

99%

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Synonym(s):
VEC, Vinyl ethylene carbonate
Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
Molecular Weight:
114.10
MDL number:
PubChem Substance ID:

Quality Level

assay

99%

refractive index

n20/D 1.45 (lit.)

bp

237 °C/733 mmHg (lit.)

density

1.188 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CC1COC(=O)O1

InChI

1S/C5H6O3/c1-2-4-3-7-5(6)8-4/h2,4H,1,3H2

InChI key

BJWMSGRKJIOCNR-UHFFFAOYSA-N

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1 of 4

This Item
230995V3409556084
vibrant-m

496820

4-Vinyl-1,3-dioxolan-2-one

vibrant-m

230995

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

vibrant-m

V3409

1-Vinyl-2-pyrrolidinone

vibrant-m

556084

1-Vinyl cyclohexanol

assay

99%

assay

96%

assay

≥99%

assay

97%

density

1.188 g/mL at 25 °C (lit.)

density

1.542 g/mL at 25 °C (lit.)

density

1.04 g/mL at 25 °C (lit.)

density

0.942 g/mL at 25 °C (lit.)

refractive index

n20/D 1.45 (lit.)

refractive index

n20/D 1.479 (lit.)

refractive index

n20/D 1.512 (lit.)

refractive index

n20/D 1.478 (lit.)

bp

237 °C/733 mmHg (lit.)

bp

68-70 °C/8 mmHg (lit.)

bp

92-95 °C/11 mmHg (lit.)

bp

74 °C/19 mmHg (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

General description

4-Vinyl-1,3-dioxolan-2-one (VEC) is a cyclic carbonate, that can be synthesized from acrolein by reacting with sulfur ylide and CO2. The ruthenium-catalyzed transfer hydrogenation (TH) of VEC in the presence of 2-propanol forms 1,2-butanediol. Indolines and indoles undergo selective C-H allylation with VEC in the presence of rhodium(III) catalyst.

Application

4-Vinyl-1,3-dioxolan-2-one may be used in the preparation of 2-arylbenzo[d]thiazole scaffolds.
It may be used in the synthesis of the following multi-functional cyclic carbonates:
  • 4,4′-((hexane-1,6-diylbis(sulfanediyl))bis-(ethane-2,1-diyl))bis(1,3-dioxolan-2-one) (Bis-CC)
  • 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)-ethyl)thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tris-CC)
  • 2,2-bis(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)-thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tetra-CC)
Used to synthesize functional polymers.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 1

flash_point_f

206.4 °F - closed cup

flash_point_c

96.9 °C - closed cup

ppe

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


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