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Merck
CN

145491

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848729
EC Number:
208-172-0
Beilstein/REAXYS Number:
605285
MDL number:
MFCD00008595
Assay:
98%
Form:
liquid

Key Documents

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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

InChI key

SDJHPPZKZZWAKF-UHFFFAOYSA-N

InChI

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

SMILES string

CC(=C)C(C)=C

vapor pressure

269 mmHg ( 37.7 °C)

assay

98%

form

liquid

contains

100 ppm BHT as stabilizer

Quality Level

200

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0253
BCBZ9229
BCBV5841
BCBV6576
BCBN7754V

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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)
Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes.
Carrera EI and Seferos DS.
Dalton Transactions, 44(5), 2092-2096 (2015)
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)
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.
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)
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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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