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145491

Sigma-Aldrich

2,3-Dimethyl-1,3-butadiene

98%, contains 100 ppm BHT as stabilizer

Sinónimos:

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

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About This Item

Fórmula lineal:
CH2=C(CH3)C(CH3)=CH2
Número de CAS:
513-81-5
Peso molecular:
82.14
Beilstein/REAXYS Number:
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)

Quality Level

200

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

signalword

Danger

hcodes

H225

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCK0253
BCBZ9229
BCBV5841
BCBV6576
BCBN7754V

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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)
Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes.
Carrera EI and Seferos DS.
Dalton Transactions, 44(5), 2092-2096 (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.
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)
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Artículos

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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