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127574

Sigma-Aldrich

3,4-Epoxy-1-butene

98%

Synonym(s):

2-Vinyloxirane, 3,4-Epoxy-1-butene, Butadiene monoxide

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About This Item

Empirical Formula (Hill Notation):
C4H6O
CAS Number:
930-22-3
Molecular Weight:
70.09
Beilstein/REAXYS Number:
103170
EC Number:
213-210-4
MDL number:
MFCD00005149
UNSPSC Code:
12162002
PubChem Substance ID:
24847787
NACRES:
NA.23

assay

98%

form

liquid

refractive index

n20/D 1.417 (lit.)

bp

65-66 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CC1CO1

InChI

1S/C4H6O/c1-2-4-3-5-4/h2,4H,1,3H2

InChI key

GXBYFVGCMPJVJX-UHFFFAOYSA-N

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accessory

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Description
Pricing

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-58.0 °F - closed cup

flash_point_c

-50 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Thomas J L Mustard et al.
Journal of the American Chemical Society, 135(4), 1471-1475 (2013-01-01)
Density functional theory computations of the Cu-catalyzed ring expansion of vinyloxiranes is mediated by a traceless dual Cu(I)-catalyst mechanism. Overall, the reaction involves a monomeric Cu(I)-catalyst, but a single key step, the Cu migration, requires two Cu(I)-catalysts for the transformation.
M W Himmelstein et al.
Chemico-biological interactions, 135-136, 703-713 (2001-06-09)
(1-Chloroethenyl)oxirane (CEO) is a metabolite of beta-chloroprene (2-chloro-1,3-butadiene, CD). The purpose of this study was to evaluate the in vitro mutagenic and clastogenic (chromosome breaking) potential of CEO. For comparative purposes, the study also included an evaluation of the racemic
A D Kligerman et al.
Chemico-biological interactions, 166(1-3), 132-139 (2006-05-16)
1,3-Butadiene (BTD) is an important commodity chemical and air pollutant that has been shown to be a potent carcinogen in mice, and to a lesser extent, a carcinogen in rats. To better assess butadiene's carcinogenic risk to humans, it is
L Recio et al.
Chemico-biological interactions, 135-136, 325-341 (2001-06-09)
1,3-Butadiene (BD) is a multisite carcinogen and is mutagenic in multiple tissues of B6C3F1 mice. BD is bioactivated to at least three directly mutagenic metabolites: 1,2-epoxybutene (EB), 1,2-epoxy-3,4-butanediol (EBD), and 1,2,3,4-diepoxybutane (DEB). However, the contribution of these individual metabolites to
Gunnar Boysen et al.
Chemico-biological interactions, 166(1-3), 170-175 (2007-02-15)
1,3-Butadiene is metabolized mainly by cytochrome P450 2E1 to several epoxides that are considered toxic and carcinogenic. The first step of BD metabolism is oxidation to 1,2-epoxy-3-butene (EB), a reactive metabolite. It has been shown that P450s can be inactivated
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