2,3-Dimethoxy-1,3-butadiene

HCID 19169

Notes Reactions

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Basic information

CAS: 3588-31-6
Standard SMILES: C=C(OC)C(=C)OC
InChIKey: NHBDKDZHQKQPTF-UHFFFAOYSA-N
Molecular formula: C6H10O2
Average molar mass: 114.14 g/mol
Monoisotopic mass: 114.06807956

Names & identifiers

Preferred name: 2,3-Dimethoxy-1,3-butadiene
IUPAC: 2,3-dimethoxybuta-1,3-diene
English name: 2,3-Dimethoxy-1,3-butadiene
Molecular formula: C6H10O2
Molecular weight: 114.14

Names & synonyms

2,3-DIMETHOXY-1,3-BUTADIENE3588-31-6DTXSID30189438RefChem:81785DTXCID60111929626-576-9NHBDKDZHQKQPTF-UHFFFAOYSA-N2,3-dimethoxybuta-1,3-diene1,3-Butadiene, 2,3-dimethoxy-rans,trans-1,3-Butadiene-1,4-dicarboxylic acid23-Dimethoxy-13-butadieneSCHEMBL1721841

Show more names

2,3-Dimethoxy-1,3-bu2,3-DIMETHOLXY-1,3-BUTADIENE2,3-DIMETHOXY-1,3-BUTADIENCEAminocaproic acid impurities32,3-Dimethoxy-1,3-butadiene 95%

2,3-Dimethoxy-buta-1,3-dieneAKOS0159124372,3-Dimethoxy-1,3-butadiene, 95%EN300-85834G77336

Database identifiers

CAS: 3588-31-6
PubChem CID: 19169
DTXSID: DTXSID30189438
EC Number: 626-576-9
Nikkaji: J496.084J

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 18.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 8
Formal charge: 0
Complexity: 91.1

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Physicochemical properties

Melting point: 19 °C · 19 °C (lit.)
Boiling point: 134 · 134-136 °C/745 mmHg (lit.)
Density: 0.94 g/mL · 0.94 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.459(lit.)
Flash point: 91 °F · 91 °F
storage temp.: 2 · 2-8°C
form: liquid
InChI: 1S/C6H10O2/c1-5(7-3)6(2)8-4/h1-2H2,3-4H3
InChIKey: NHBDKDZHQKQPTF-UHFFFAOYSA-N
SMILES: COC(=C)C(=C)OC
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Warning
Hazard statements: 226 · H226
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Risk Statements: 10 · 10
Safety Statements: 16 · 16-33
RIDADR: 1993 · UN 1993 3/PG 3
WGK Germany: 3 · 3
HazardClass: 3.2 · 3.2
PackingGroup: III
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 · Flam. Liq. 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 1993 3/PG 3
risk_code: 10
Signal word: Warning
Symbol(GHS): GHS02
safety_code: 16-33
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226
Hazard Classifications: Flam. Liq. 3

Chemistry & industry

Applications · 2 items

Uses2,3-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.

General Description2,3-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.