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Sigma-Aldrich

2,3-Dimethyl-1,3-butadiene

98%, contains 100 ppm BHT as stabilizer

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Synonym(s):
2,3-Dimethylbuta-1,2-diene, 2,3-Dimethylenebutane, Biisopropenyl, Diisopropenyl
Linear Formula:
CH2=C(CH3)C(CH3)=CH2
CAS Number:
513-81-5
Molecular Weight:
82.14
Beilstein:
605285
EC Number:
208-172-0
MDL number:
MFCD00008595
PubChem Substance ID:
24848729
NACRES:
NA.22

vapor pressure

269 mmHg ( 37.7 °C)

Assay

98%

form

liquid

contains

100 ppm BHT as stabilizer

refractive index

n20/D 1.438 (lit.)

bp

68-69 °C (lit.)

mp

−76 °C (lit.)

density

0.726 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(C)=C

InChI

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

InChI key

SDJHPPZKZZWAKF-UHFFFAOYSA-N

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General description

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.

Application

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.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

30.2 °F - closed cup

Flash Point(C)

-1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Aryl (hetaryl)-containing gem-cyanonitroethenes: Synthesis, structure, and reactions with 2,3-dimethyl-1,3-butadiene.
Baichurin RI, et al.
Russ. J. Gen. Chem., 85(8), 1845-1854 (2015)
Cycloaddition chemistry of 1, 3-dienes on the silicon (001) surface: Competition between [4+ 2] and [2+ 2] reactions.
Hovis JS, et al.
The Journal of Physical Chemistry B, 102(35), 6873-6879 (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.
Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes.
Carrera EI and Seferos DS.
Dalton Transactions, 44(5), 2092-2096 (2015)
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
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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.

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