3588-31-6

Basic information

• Product Name: 2,3-Dimethoxy-1,3-butadiene
• Synonyms: 2,3-DIMETHOXY-1,3-BUTADIENE;2,3-Dimethoxy-buta-1,3-Diene;2,3-DIMETHOXY-1,3-BUTADIENCE;2,3-DIMETHOLXY-1,3-BUTADIENE;2,3-Dimethoxy-1,3-bu;2,3-Dimethoxy-1,3-butadiene 95%
• CAS NO: 3588-31-6
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Product Categories: Enol Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;Chemical Synthesis;Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 3588-31-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 19 °C(lit.)
• Boiling Point: 134-136 °C745 mm Hg(lit.)
• Flash Point: 91 °F
• Appearance: /
• Density: 0.94 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.76mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,3-Dimethoxy-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxy-1,3-butadiene(3588-31-6)
• EPA Substance Registry System: 2,3-Dimethoxy-1,3-butadiene(3588-31-6)

Safety Data

• Statements: 10
• Safety Statements: 16-33
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 3588-31-6(Hazardous Substances Data)

Usage

Uses

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.

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.

InChI:InChI=1/C6H10O2/c1-5(7-3)6(2)8-4/h1-2H2,3-4H3

Synthetic route

dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → 2,3-dimethoxy-1,3-butadiene (3588-31-6)

Conditions	Yield
With sulfuric acid In methanol for 12h; Heating;	73%
With sulfuric acid In methanol for 10h; Reflux;	68%
Stage #1: dimethylglyoxal; trimethyl orthoformate With sulfuric acid In methanol for 10h; Reflux; Stage #2: With ammonium dihydrogen phosphate; hydroquinone In methanol at 100 - 110℃;	68%

methanol (67-56-1) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → 2,3-dimethoxy-1,3-butadiene (3588-31-6)

Conditions	Yield
sulfuric acid for 10h; Heating / reflux;	68%

meso-1,4-diiodo-2,3-dimethoxy-butane (58313-64-7) → 2,3-dimethoxy-1,3-butadiene (3588-31-6)

Conditions	Yield
With sodium hydroxide; ethoxyethoxyethanol at 200℃;

1,4-diiodo-2,3-dimethoxy-butane (6963-02-6) → 2,3-dimethoxy-1,3-butadiene (3588-31-6)

Conditions	Yield
With sodium hydroxide at 160℃;

meso-1,4-diiodo-2,3-dimethoxy-butane (58313-64-7) + ethoxyethoxyethanol (111-90-0) + concentrated NaOH → 2,3-dimethoxy-1,3-butadiene (3588-31-6)

Conditions	Yield
at 200℃;

diethyl diazodicarboxylate (4143-61-7) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → diethyl 4,5-dimethoxy-1,2,3,6-tetrahydro-1,2-pyridazincarboxylate

Conditions	Yield
With lanthanum(lll) triflate at 20℃; for 0.5h; hetero-Diels-Alder reaction;	98%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + diazodimedone (1807-68-7) → 2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Conditions	Yield
With rhodium(II) pivalate at 20℃; for 3h;	98%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2-diazo-1H-phenalene-1,3(2H)-dione (18931-19-6) → 9-methoxy-9-(1-methoxyvinyl)-8,9-dihydrophenaleno[1,2-b]furan-7-one

Conditions	Yield
With rhodium(II) pivalate at 20℃; for 3h;	98%

5-nitro[2.2]paracyclophanepyran-6-one (872221-35-7) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → C25H25NO6

Conditions	Yield
With hydroquinone In dichloromethane at 50℃; under 6000600 Torr; for 20h; Diels-Alder reaction;	98%

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine (35024-12-5) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → 2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Conditions	Yield
rhodium(II) pivalate at 20℃; for 12h;	90%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + selenobenzophenone (119579-98-5) → 3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran (128632-63-3)

Conditions	Yield
Ambient temperature;	88%
In toluene for 24h; Ambient temperature; Yield given;

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2,2,4,4-tetraphenyl-1,3-diselenacyclobutane (128632-60-0) → 3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran (128632-63-3)

Conditions	Yield
In toluene for 6h; Ambient temperature;	88%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione (152420-82-1) → 5,6-dihydro-3,4-dimethoxy-6,6-diacetyl-2H-thiopyran

Conditions	Yield
With pyridine In chloroform Ambient temperature;	88%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 3-diazobenzopyran-2,4(3H)-dione (5186-54-9) → 2-methoxy-2-(1-methoxyvinyl)-2,3-dihydrofuro[3,2-c]chromen-4-one

Conditions	Yield
With rhodium(II) pivalate at 60℃; for 3h;	87%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 1-methylquinolin-2(1H)-one-4-carbaldehyde (15112-98-8) → cis-10a-formyl-5,6,6a,7,10,10a-hexahydro-8,9-dimethoxy-5-methylphenanthridin-6-one

Conditions	Yield
In o-xylene at 200℃; for 72h; Diels-Alder reaction;	86%

5,8-quinolinedione (10470-83-4) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → 6,7-dimethoxy-1-azaanthracene-9,10-dione (101402-87-3)

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane for 0.5h; Ambient temperature;	85%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + C18H22B2N2O2 → 2-(3,4-dimethoxy-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Conditions	Yield
In toluene at 180℃; for 12h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;	85%

glycolic Acid (79-14-1) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → (+/-)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-one

Conditions	Yield
With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h;	83%
With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h;	83%
With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h;	83%
With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h;	83%
With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h;	83%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2-methoxycarbonyl-1,4-naphthoquinone (83575-14-8) → methyl 5-hydroxy-2-methoxy-2-(1-methoxyvinyl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate (1452153-42-2)

Conditions	Yield
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 0.333333h;	81%
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 0.333333h;	81%

3-nitrocoumarin (28448-04-6) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → 8,9-dimethoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one

Conditions	Yield
In 1,2-dichloro-ethane at 90℃; for 6h; Diels-Alder reaction;	80%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 4-Fluoronitrobenzene (350-46-9) → 2-(4-fluorophenyl)-4,5-dimethoxy-3,6-dihydro-2H-[1,2]-oxazine

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); 1,10-Phenanthroline; phenyl formate; triethylamine In acetonitrile at 140℃; for 4h; Diels-Alder Cycloaddition; Inert atmosphere; Sealed tube; Schlenk technique;	79%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + [(C5H5)Re(NO)(triphenylphosphite)(SCHC6H5)] hexafluorophosphate → [(C5H5)Re(NO)(triphenylphosphite)(SC5H5(C6H5)(OCH3)2)] hexafluorophosphate

Conditions	Yield
In dichloromethane N2 atmosphere, 20°C; concn. to dryness, recrystn. (CH2Cl2/pentane), 24% de; elem. anal.;	78%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + (E)-1,4-Bis-(4-tert-butyl-phenyl)-but-2-ene-1,4-dione → [6-(4-tert-Butyl-benzoyl)-3,4-dimethoxy-cyclohex-3-enyl]-(4-tert-butyl-phenyl)-methanone

Conditions	Yield
	75%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 3,4-dichloro-6-fluoro-2H-chromen-2-one → 2-fluoro-8,9-dimethoxy-6H-benzo[c]chromen-6-one (1493784-07-8)

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; 3,4-dichloro-6-fluoro-2H-chromen-2-one In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	74%
Stage #1: 2,3-dimethoxy-1,3-butadiene; 3,4-dichloro-6-fluoro-2H-chromen-2-one In benzene for 5h; UV-irradiation; Stage #2: With silica gel at 100℃; for 8.5h; Darkness; Stage #3: In acetone for 7h; UV-irradiation;	73.8%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 3,4-dichloro-8-phenyl-2H-chromen-2-one → 8,9-dimethoxy-4-phenyl-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; 3,4-dichloro-8-phenyl-2H-chromen-2-one In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	74%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + glycerol (56-81-5) → (2R*,3R*,6S*)-2,3,6,7-Tetrahydro-3-methoxy-2,3-dimethyl-5H-2,6-epoxy-1,4-dioxepine

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; glycerol With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 24h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃;	73%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione (152420-82-1) → 1-(4a,7,8,8a-tetrahydro-2-methyl-4a,8a-dimethoxy-7,7-diacetyl-5H-thiopyrano<2,3-c><1,4>oxathiin-3-yl)ethanone

Conditions	Yield
With pyridine In chloroform Ambient temperature;	72%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 3,4-dichloro-6-phenyl-2H-chromen-2-one → 8,9-dimethoxy-2-phenyl-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; 3,4-dichloro-6-phenyl-2H-chromen-2-one In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	72%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 2,2'-(ethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (339166-89-1) → 2,2'-(3,4-dimethoxycyclohex-3-ene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
In toluene at 180℃; for 12h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;	72%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 3,4,6-trichloro-2H-chromen-2-one (5196-72-5) → 2-chloro-8,9-dimethoxy-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; 3,4,6-trichloro-2H-chromen-2-one In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	71%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + 6-bromo-3,4-dichloro-2H-chromen-2-one (63795-99-3) → 2-bromo-8,9-dimethoxy-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; 6-bromo-3,4-dichloro-2H-chromen-2-one In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	71%

3,4-dichloro-6-methyl-2H-chromen-2-one (15736-24-0) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → 8,9-dimethoxy-2-methyl-6H-benzo[c]chromen-6-one (129194-48-5)

Conditions	Yield
Stage #1: 3,4-dichloro-6-methyl-2H-chromen-2-one; 2,3-dimethoxy-1,3-butadiene In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	71%

3,4-dichloro-2H-chromen-2-one (5117-56-6) + 2,3-dimethoxy-1,3-butadiene (3588-31-6) → 8,9-dimethoxy-6H-benzo[b]chromin-6-one

Conditions	Yield
Stage #1: 3,4-dichloro-2H-chromen-2-one; 2,3-dimethoxy-1,3-butadiene In benzene for 4h; Diels-Alder Cycloaddition; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Stage #3: In acetone for 9h; UV-irradiation;	71%
Stage #1: 3,4-dichloro-2H-chromen-2-one; 2,3-dimethoxy-1,3-butadiene In benzene for 5h; UV-irradiation; Stage #2: With silica gel at 100℃; for 4h; Darkness; Stage #3: In acetone for 5h; UV-irradiation;	52.3%

2,3-dimethoxy-1,3-butadiene (3588-31-6) + dimethyl L-tartrate (608-68-4) → (2R,3R,5R,6R)-5,6-Dimethoxy-5-methyl-[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester

Conditions	Yield
Stage #1: 2,3-dimethoxy-1,3-butadiene; dimethyl L-tartrate With triphenylphosphine hydrobromide In dichloromethane at 20℃; for 3h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃;	70%

Upstream product

• 58313-64-7 meso-1,4-diiodo-2,3-dimethoxy-butane 
• 431-03-8 dimethylglyoxal 
• 149-73-5 trimethyl orthoformate 
• 111-90-0 ethoxyethoxyethanol 
• 67-56-1 methanol 
• 6963-02-6 1,4-diiodo-2,3-dimethoxy-butane 

Downstream Products

• 431-03-8 dimethylglyoxal 
• 22506-55-4 2,3-dimethoxy-anthraquinone 
• 100137-04-0 4.4.5.5-Tetracyano-1.2-dimethoxy-cyclohexen-⁽¹⁾ 
• 128632-63-3 3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran 
• 553-90-2 Dimethyl oxalate 
• 7001-18-5 methyl 2-methoxyacrylate 
• 10027-72-2 methoxymethyl hydroperoxide 
• 143429-25-8 2,3,3-Trimethoxy-4-hydroxy-1-butene 
• 143429-27-0 3-Methoxy-3-(1-methoxyethenyl)-1,2-dioxolane 
• 143429-26-9 3-Methoxy-3-(1-methoxyethenyl)-1,2,4-trioxolane 
• 143429-24-7 3-(Carboxymethyl)-3-methoxy-1,2-dioxolane 
• 143429-23-6 3-(Carboxymethyl)-3-methoxy-1,2,4-trioxolane 
• 51792-34-8 2,3-dimethoxythiophene 
• 38088-95-8 8-methoxyphenanthridine-6(5H)-one 

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