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276030

Sigma-Aldrich

2,3-Dimethoxy-1,3-butadiene

95%

Synonym(s):

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

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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
Pricing and availability is not currently available.

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.)

functional group

ether

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.[1] 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.[2] It forms adducts with graphene and Diels-Alder chemistry in this formation has been investigated.[3]

Application

2,3-Dimethoxy-1,3-butadiene has been employed as diene to investigate the Diels-Alder chemistry of pristine and defective graphene.[4] It was also used in the synthesis of novel benzopentathiepin varacinium trifluoroacetate.[5]
It may be used in the preparation of 3,4-dimethoxythiophene, an intermediate for the synthesis of 3,4-ethylenedioxythiophene (EDOT).[6] It may also be used to form thio esters by reacting with mercaptans in the presence of cobalt carbonyl catalyst.[7]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS6040
MKBW8237V
MKBS1853V
MKBR7575V
MKBB9274V

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Pablo A Denis
Chemistry (Weinheim an der Bergstrasse, Germany), 19(46), 15719-15725 (2013-10-12)
Herein, by using dispersion-corrected density functional theory, we investigated the Diels-Alder chemistry of pristine and defective graphene. Three dienes were considered, namely 2,3-dimethoxy-1,3-butadiene (DMBD), 9-methylanthracene (9MA), and 9,10-dimethylanthracene (910DMA). The dienophiles that were assayed were tetracyanoethylene (TCNE) and maleic anhydride
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
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)
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)
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
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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. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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