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145491

Sigma-Aldrich

2,3-Dimethyl-1,3-butadiene

98%, contains 100 ppm BHT as stabilizer

Sinônimo(s):

2,3-Dimethylbuta-1,2-diene, 2,3-Dimethylenebutane, Biisopropenyl, Diisopropenyl

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About This Item

Fórmula linear:
CH2=C(CH3)C(CH3)=CH2
Número CAS:
513-81-5
Peso molecular:
82.14
Beilstein:
605285
Número CE:
208-172-0
Número MDL:
MFCD00008595
Código UNSPSC:
12352100
ID de substância PubChem:
24848729
NACRES:
NA.22

pressão de vapor

269 mmHg ( 37.7 °C)

Nível de qualidade

200

Ensaio

98%

forma

liquid

contém

100 ppm BHT as stabilizer

índice de refração

n20/D 1.438 (lit.)

pb

68-69 °C (lit.)

pf

−76 °C (lit.)

densidade

0.726 g/mL at 25 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CC(=C)C(C)=C

InChI

1S/C6H10/c1-5(2)6(3)4/h1,3H2,2,4H3

chave InChI

SDJHPPZKZZWAKF-UHFFFAOYSA-N

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Descrição geral

2,3-Dimethyl-1,3-butadiene (DMBD) is a conjugated diene. It undergoes Diels Alder cycloaddition reaction with 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions. It undergoes thermal [4+2] cycloaddition reaction with 3-acetyl-, 3-carbamoyl and 3-ethoxycarbonylcoumarins under solvent free conditions. DMBD participates in polymerization reactions in the presence of iron dichloride complexes based catalysts.

Aplicação

2,3-Dimethyl-1,3-butadiene was used to investigate the reactions of 1,3-dienes with the Si(001) surface using scanning tunneling microscopy and fourier transform infrared spectroscopy.
It may be used in the following processes:
  • Preparation of 1,3,6-triene derivatives of corresponding 1-aryl-substituted 1,3-dienes by 1,4-hydrobutadienylation in the presence of cobalt catalyst.
  • Synthesis of 6-aryl(hetaryl)-3,4-dimethyl-1-nitro-1-cyano-3-cyclohexenes by reacting with gem-cyanonitroethenes.
  • As a halogen trap during the study of the photolysis reaction of dibromo adduct of 2,5-diphenyltellurophene.

Pictogramas

Flame
GHS02

Palavra indicadora

Danger

Frases de perigo

H225

Declarações de precaução

P210 - P233 - P240 - P241 - P242 - P243

Classificações de perigo

Flam. Liq. 2

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

30.2 °F - closed cup

Ponto de fulgor (°C)

-1 °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
BCBZ9229
BCBV5841
BCBV6576
BCBN7754V
BCBG3964V

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Sigma-Aldrich

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Polymerization of 1, 3-dienes with iron complexes based catalysts: Influence of the ligand on catalyst activity and stereospecificity.
Ricci G, et al.
J. Mol. Catal. A: Chem., 204, 287-293 (2003)
Cobalt-Catalyzed 1, 4-Hydrobutadienylation of 1-Aryl-1,3-dienes with 2,3-Dimethyl-1,3-butadiene.
Bohn MA, et al.
Angewandte Chemie (International Edition in English), 50(41), 9689-9693 (2011)
Irma Y Flores-Larios et al.
Molecules (Basel, Switzerland), 15(3), 1513-1530 (2010-03-26)
The thermal [4+2] cycloadditions of 3-acetyl-, 3-carbamoyl, and 3-ethoxycarbonylcoumarins with 2,3-dimethyl-1,3-butadiene under solvent free conditions are reported, as well as the epoxidation reactions of some adducts. Discussion is focused on the structural features of the Diels-Alder adducts and their epoxides
Peroxy radical kinetics resulting from the OH-initiated oxidation of 1,3-butadiene, 2,3-dimethyl-1,3-butadiene and isoprene.
Jenkin ME, et al.
Journal of Atmospheric Chemistry, 29(3), 267-298 (1998)
Marie Kissane et al.
Organic & biomolecular chemistry, 8(24), 5602-5613 (2010-10-12)
The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed.
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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. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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