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496820

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

99%

Sustainability features

Synonym(s):

VEC, Vinyl ethylene carbonate

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About This Item

Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
4427-96-7
Molecular Weight:
114.10
NACRES:
NA.22
PubChem Substance ID:
24873085
UNSPSC Code:
12352100
MDL number:
MFCD00143315
Assay:
99%
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Quality Segment

assay

99%

sustainability

Sustainability features

refractive index

n20/D 1.45 (lit.)

bp

237 °C/733 mmHg (lit.)

density

1.188 g/mL at 25 °C (lit.)

functional group

carbonate

greener alternative category

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

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.
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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.

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Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Codes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

Flash Point (°F)

206.4 °F - closed cup

Flash Point (°C)

96.9 °C - closed cup

PPE (personal protective equipment)

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

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