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145491

Sigma-Aldrich

2,3-Dimethyl-1,3-butadiene

98%, contains 100 ppm BHT as stabilizer

Synonym(s):

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

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About This Item

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
UNSPSC Code:
12352100
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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)
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)
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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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