Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

276030

Sigma-Aldrich

2,3-Dimethoxy-1,3-butadiene

95%

Synonym(s):

2,3-Dimethoxybuta-1,3-diene, 2,3-Dimethoxybutadiene

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
H2C=C(OCH3)C(OCH3)=CH2
CAS Number:
3588-31-6
Molecular Weight:
114.14
MDL number:
MFCD00010229
UNSPSC Code:
12352100
PubChem Substance ID:
24856688
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.459 (lit.)

bp

134-136 °C/745 mmHg (lit.)

mp

19 °C (lit.)

density

0.94 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=C)C(=C)OC

InChI

1S/C6H10O2/c1-5(7-3)6(2)8-4/h1-2H2,3-4H3

InChI key

NHBDKDZHQKQPTF-UHFFFAOYSA-N

General description

2,3-Dimethoxy-1,3-butadiene (DMEBD) is a 1,3-butadiene derivative. The reaction kinetics of hydrolysis of 2,3-dimethoxy-1,3-butadiene in the presence of acid catalyst has been investigated. The [4+2] cycloadditions of 3-nitrocoumarins with DMEBD has been investigated in aqueous medium, in organic solvent and under solventless conditions. This reaction led to the formation of 4-substituted 3-nitrochromanones. It forms adducts with graphene and Diels-Alder chemistry in this formation has been investigated.

Application

2,3-Dimethoxy-1,3-butadiene has been employed as diene to investigate the Diels-Alder chemistry of pristine and defective graphene. It was also used in the synthesis of novel benzopentathiepin varacinium trifluoroacetate.
It may be used in the preparation of 3,4-dimethoxythiophene, an intermediate for the synthesis of 3,4-ethylenedioxythiophene (EDOT). It may also be used to form thio esters by reacting with mercaptans in the presence of cobalt carbonyl catalyst.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBW8237V
MKBS1853V
MKBR7575V
MKBB9274V
MKBB9274

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Influence of dienes on the cobalt carbonyl catalyzed reaction of mercaptans with carbon monoxide.
Antebi S and Alper H.
Organometallics, 5(3), 596-598 (1986)
Santanu Sarkar et al.
Journal of the American Chemical Society, 133(10), 3324-3327 (2011-02-24)
The zero-band-gap electronic structure of graphene enables it to function as either the diene or the dienophile in the Diels-Alder reaction, and this versatile synthetic method offers a powerful strategy for the reversible modification of the electronic properties of graphene
Vinyl ether hydrolysis. XVIII. The two-stage reaction of 2,3-dimethoxy-1,3-butadiene.
Kresge AJ and Yin Y.
Canadian Journal of Chemistry, 65(8), 1753-1756 (1987)
Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of" varacin-free base.
Behar V, et al.
Journal of the American Chemical Society, 115(15), 7017-7018 (1993)
David Amantini et al.
The Journal of organic chemistry, 68(24), 9263-9268 (2003-11-25)
The [4 + 2] cycloadditions of 3-nitrocoumarin (1a), 6-chloro-3-nitrocoumarin (1b), and 6-, 7-, and 8-hydroxy-3-nitrocoumarins (1c, 5, and 6) with (E)-piperylene (7), isoprene (8), 2,3-dimethyl-1,3-butadiene (9), 2-methoxy-1,3-butadiene (10), 2,3-dimethoxy-1,3-butadiene (11), and cyclopentadiene (12) were investigated in aqueous medium, in organic
View All Related Papers

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service