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Sigma-Aldrich

2,3-Dimethoxy-1,3-butadiene

95%

Sinônimo(s):

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

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About This Item

Fórmula linear:
H2C=C(OCH3)C(OCH3)=CH2
Número CAS:
3588-31-6
Peso molecular:
114.14
Número MDL:
MFCD00010229
Código UNSPSC:
12352100
ID de substância PubChem:
24856688
NACRES:
NA.22

Ensaio

95%

Formulário

liquid

índice de refração

n20/D 1.459 (lit.)

p.e.

134-136 °C/745 mmHg (lit.)

pf

19 °C (lit.)

densidade

0.94 g/mL at 25 °C (lit.)

grupo funcional

ether

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

COC(=C)C(=C)OC

InChI

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

chave InChI

NHBDKDZHQKQPTF-UHFFFAOYSA-N

Descrição geral

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.

Aplicação

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.

Pictogramas

Flame
GHS02

Palavra indicadora

Warning

Frases de perigo

H226

Classificações de perigo

Flam. Liq. 3

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

91.4 °F - closed cup

Ponto de fulgor (°C)

33 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
MKBW8237V
MKBS1853V
MKBR7575V
MKBB9274V
MKBB9274

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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
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Artigos

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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