276030

2,3-Dimethoxy-1,3-butadiene

95%

• Synonym(s): 2,3-Dimethoxybuta-1,3-diene, 2,3-Dimethoxybutadiene
• Linear Formula: H₂C=C(OCH₃)C(OCH₃)=CH₂
• CAS Number: 3588-31-6
• Molecular Weight: 114.14
• MDL number: MFCD00010229
• UNSPSC Code: 12352100
• PubChem Substance ID: 24856688
• NACRES: NA.22

Properties

• Assay: 95%
• form: liquid
• refractive index: n20/D 1.459 (lit.)
• bp: 134-136 °C/745 mmHg (lit.)
• mp: 19 °C (lit.)
• density: 0.94 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: COC(=C)C(=C)OC
• InChI: 1S/C6H10O2/c1-5(7-3)6(2)8-4/h1-2H2,3-4H3
• InChI key: NHBDKDZHQKQPTF-UHFFFAOYSA-N

Description

General description

2,3-Dimethoxy-1,3-butadiene (DMEBD) is a 1,3-butadiene derivative. The reaction kinetics of hydrolysis of 2,3-dimethoxy-1,3-butadiene in the presence of acid catalyst has been investigated. The [4+2] cycloadditions of 3-nitrocoumarins with DMEBD has been investigated in aqueous medium, in organic solvent and under solventless conditions. This reaction led to the formation of 4-substituted 3-nitrochromanones. It forms adducts with graphene and Diels-Alder chemistry in this formation has been investigated.

Application

2,3-Dimethoxy-1,3-butadiene has been employed as diene to investigate the Diels-Alder chemistry of pristine and defective graphene. It was also used in the synthesis of novel benzopentathiepin varacinium trifluoroacetate.
It may be used in the preparation of 3,4-dimethoxythiophene, an intermediate for the synthesis of 3,4-ethylenedioxythiophene (EDOT). It may also be used to form thio esters by reacting with mercaptans in the presence of cobalt carbonyl catalyst.

Safety Information

• Pictograms: GHS02
• Signal Word: Warning
• Hazard Statements: H226
• Hazard Classifications: Flam. Liq. 3
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 91.4 °F - closed cup
• Flash Point(C): 33 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves