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2,3-Dimethoxy-1,3-butadiene is an organic compound that features a conjugated diene system with two methoxy groups attached to the terminal carbons. This structure endows it with unique chemical reactivity and properties, making it a versatile building block in organic synthesis.

3588-31-6

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3588-31-6 Usage

Uses

Used in Chemical Research:
2,3-Dimethoxy-1,3-butadiene is used as a diene in the study of Diels-Alder chemistry, particularly for investigating the reactivity of pristine and defective graphene. Its ability to participate in [4+2] cycloaddition reactions makes it a valuable compound for exploring new pathways in material science and organic chemistry.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2,3-Dimethoxy-1,3-butadiene is utilized as a key intermediate in the synthesis of novel compounds with potential therapeutic applications. For instance, it has been used in the synthesis of benzopentathiepin varacinium trifluoroacetate, a compound that may exhibit unique biological activities.
Used in Polymer Synthesis:
2,3-Dimethoxy-1,3-butadiene may be employed in the preparation of 3,4-dimethoxythiophene, which is an important intermediate for the synthesis of 3,4-ethylenedioxythiophene (EDOT). EDOT is a monomer used in the production of conductive polymers, such as poly(3,4-ethylenedioxythiophene), which have applications in organic electronics, including organic solar cells and field-effect transistors.
Used in the Production of Thio Esters:
2,3-Dimethoxy-1,3-butadiene can also be used to form thio esters by reacting with mercaptans in the presence of a cobalt carbonyl catalyst. Thio esters are valuable synthetic intermediates and have applications in the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and fragrances.

Check Digit Verification of cas no

The CAS Registry Mumber 3588-31-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,8 and 8 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3588-31:
(6*3)+(5*5)+(4*8)+(3*8)+(2*3)+(1*1)=106
106 % 10 = 6
So 3588-31-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-5(7-3)6(2)8-4/h1-2H2,3-4H3

3588-31-6 Well-known Company Product Price

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  • Aldrich

  • (276030)  2,3-Dimethoxy-1,3-butadiene  95%

  • 3588-31-6

  • 276030-1G

  • 1,611.09CNY

  • Detail
  • Aldrich

  • (276030)  2,3-Dimethoxy-1,3-butadiene  95%

  • 3588-31-6

  • 276030-5G

  • 5,799.69CNY

  • Detail

3588-31-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,3-dimethoxybuta-1,3-diene

1.2 Other means of identification

Product number -
Other names 2,3-dimethoxybutadiene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3588-31-6 SDS

3588-31-6Synthetic route

dimethylglyoxal
431-03-8

dimethylglyoxal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

Conditions
ConditionsYield
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

methanol

dimethylglyoxal
431-03-8

dimethylglyoxal

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

Conditions
ConditionsYield
sulfuric acid for 10h; Heating / reflux;68%
meso-1,4-diiodo-2,3-dimethoxy-butane
58313-64-7

meso-1,4-diiodo-2,3-dimethoxy-butane

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

Conditions
ConditionsYield
With sodium hydroxide; ethoxyethoxyethanol at 200℃;
1,4-diiodo-2,3-dimethoxy-butane
6963-02-6

1,4-diiodo-2,3-dimethoxy-butane

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

Conditions
ConditionsYield
With sodium hydroxide at 160℃;
meso-1,4-diiodo-2,3-dimethoxy-butane
58313-64-7

meso-1,4-diiodo-2,3-dimethoxy-butane

ethoxyethoxyethanol
111-90-0

ethoxyethoxyethanol

concentrated NaOH

concentrated NaOH

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

Conditions
ConditionsYield
at 200℃;
diethyl diazodicarboxylate
4143-61-7

diethyl diazodicarboxylate

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

diethyl 4,5-dimethoxy-1,2,3,6-tetrahydro-1,2-pyridazincarboxylate

diethyl 4,5-dimethoxy-1,2,3,6-tetrahydro-1,2-pyridazincarboxylate

Conditions
ConditionsYield
With lanthanum(lll) triflate at 20℃; for 0.5h; hetero-Diels-Alder reaction;98%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

diazodimedone
1807-68-7

diazodimedone

2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Conditions
ConditionsYield
With rhodium(II) pivalate at 20℃; for 3h;98%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

2-diazo-1H-phenalene-1,3(2H)-dione
18931-19-6

2-diazo-1H-phenalene-1,3(2H)-dione

9-methoxy-9-(1-methoxyvinyl)-8,9-dihydrophenaleno[1,2-b]furan-7-one

9-methoxy-9-(1-methoxyvinyl)-8,9-dihydrophenaleno[1,2-b]furan-7-one

Conditions
ConditionsYield
With rhodium(II) pivalate at 20℃; for 3h;98%
5-nitro[2.2]paracyclophanepyran-6-one
872221-35-7

5-nitro[2.2]paracyclophanepyran-6-one

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

C25H25NO6

C25H25NO6

Conditions
ConditionsYield
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

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

2-methoxy-2-(1-methoxyvinyl)-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Conditions
ConditionsYield
rhodium(II) pivalate at 20℃; for 12h;90%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

selenobenzophenone
119579-98-5

selenobenzophenone

3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran
128632-63-3

3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran

Conditions
ConditionsYield
Ambient temperature;88%
In toluene for 24h; Ambient temperature; Yield given;
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

2,2,4,4-tetraphenyl-1,3-diselenacyclobutane
128632-60-0

2,2,4,4-tetraphenyl-1,3-diselenacyclobutane

3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran
128632-63-3

3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran

Conditions
ConditionsYield
In toluene for 6h; Ambient temperature;88%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione
152420-82-1

2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione

5,6-dihydro-3,4-dimethoxy-6,6-diacetyl-2H-thiopyran

5,6-dihydro-3,4-dimethoxy-6,6-diacetyl-2H-thiopyran

Conditions
ConditionsYield
With pyridine In chloroform Ambient temperature;88%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

3-diazobenzopyran-2,4(3H)-dione
5186-54-9

3-diazobenzopyran-2,4(3H)-dione

2-methoxy-2-(1-methoxyvinyl)-2,3-dihydrofuro[3,2-c]chromen-4-one

2-methoxy-2-(1-methoxyvinyl)-2,3-dihydrofuro[3,2-c]chromen-4-one

Conditions
ConditionsYield
With rhodium(II) pivalate at 60℃; for 3h;87%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

1-methylquinolin-2(1H)-one-4-carbaldehyde
15112-98-8

1-methylquinolin-2(1H)-one-4-carbaldehyde

cis-10a-formyl-5,6,6a,7,10,10a-hexahydro-8,9-dimethoxy-5-methylphenanthridin-6-one

cis-10a-formyl-5,6,6a,7,10,10a-hexahydro-8,9-dimethoxy-5-methylphenanthridin-6-one

Conditions
ConditionsYield
In o-xylene at 200℃; for 72h; Diels-Alder reaction;86%
5,8-quinolinedione
10470-83-4

5,8-quinolinedione

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

6,7-dimethoxy-1-azaanthracene-9,10-dione
101402-87-3

6,7-dimethoxy-1-azaanthracene-9,10-dione

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane for 0.5h; Ambient temperature;85%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

C18H22B2N2O2

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

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
ConditionsYield
In toluene at 180℃; for 12h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;85%
glycolic Acid
79-14-1

glycolic Acid

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

(+/-)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-one

(+/-)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane-2-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

2-methoxycarbonyl-1,4-naphthoquinone
83575-14-8

2-methoxycarbonyl-1,4-naphthoquinone

methyl 5-hydroxy-2-methoxy-2-(1-methoxyvinyl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
1452153-42-2

methyl 5-hydroxy-2-methoxy-2-(1-methoxyvinyl)-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate

Conditions
ConditionsYield
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

3-nitrocoumarin

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

8,9-dimethoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one

8,9-dimethoxy-6a-nitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 90℃; for 6h; Diels-Alder reaction;80%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

2-(4-fluorophenyl)-4,5-dimethoxy-3,6-dihydro-2H-[1,2]-oxazine

2-(4-fluorophenyl)-4,5-dimethoxy-3,6-dihydro-2H-[1,2]-oxazine

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

[(C5H5)Re(NO)(triphenylphosphite)(SCHC6H5)] hexafluorophosphate

[(C5H5)Re(NO)(triphenylphosphite)(SCHC6H5)] hexafluorophosphate

[(C5H5)Re(NO)(triphenylphosphite)(SC5H5(C6H5)(OCH3)2)] hexafluorophosphate

[(C5H5)Re(NO)(triphenylphosphite)(SC5H5(C6H5)(OCH3)2)] hexafluorophosphate

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

(E)-1,4-Bis-(4-tert-butyl-phenyl)-but-2-ene-1,4-dione

(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

[6-(4-tert-Butyl-benzoyl)-3,4-dimethoxy-cyclohex-3-enyl]-(4-tert-butyl-phenyl)-methanone

Conditions
ConditionsYield
75%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

3,4-dichloro-6-fluoro-2H-chromen-2-one

3,4-dichloro-6-fluoro-2H-chromen-2-one

2-fluoro-8,9-dimethoxy-6H-benzo[c]chromen-6-one
1493784-07-8

2-fluoro-8,9-dimethoxy-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

3,4-dichloro-8-phenyl-2H-chromen-2-one

3,4-dichloro-8-phenyl-2H-chromen-2-one

8,9-dimethoxy-4-phenyl-6H-benzo[c]chromen-6-one

8,9-dimethoxy-4-phenyl-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

glycerol
56-81-5

glycerol

(2R*,3R*,6S*)-2,3,6,7-Tetrahydro-3-methoxy-2,3-dimethyl-5H-2,6-epoxy-1,4-dioxepine

(2R*,3R*,6S*)-2,3,6,7-Tetrahydro-3-methoxy-2,3-dimethyl-5H-2,6-epoxy-1,4-dioxepine

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione
152420-82-1

2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione

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

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
ConditionsYield
With pyridine In chloroform Ambient temperature;72%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

3,4-dichloro-6-phenyl-2H-chromen-2-one

3,4-dichloro-6-phenyl-2H-chromen-2-one

8,9-dimethoxy-2-phenyl-6H-benzo[c]chromen-6-one

8,9-dimethoxy-2-phenyl-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

2,2'-(ethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
339166-89-1

2,2'-(ethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(3,4-dimethoxycyclohex-3-ene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(3,4-dimethoxycyclohex-3-ene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
In toluene at 180℃; for 12h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;72%
2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

3,4,6-trichloro-2H-chromen-2-one
5196-72-5

3,4,6-trichloro-2H-chromen-2-one

2-chloro-8,9-dimethoxy-6H-benzo[c]chromen-6-one

2-chloro-8,9-dimethoxy-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

6-bromo-3,4-dichloro-2H-chromen-2-one
63795-99-3

6-bromo-3,4-dichloro-2H-chromen-2-one

2-bromo-8,9-dimethoxy-6H-benzo[c]chromen-6-one

2-bromo-8,9-dimethoxy-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

3,4-dichloro-6-methyl-2H-chromen-2-one

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

8,9-dimethoxy-2-methyl-6H-benzo[c]chromen-6-one
129194-48-5

8,9-dimethoxy-2-methyl-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

3,4-dichloro-2H-chromen-2-one

2,3-dimethoxy-1,3-butadiene
3588-31-6

2,3-dimethoxy-1,3-butadiene

8,9-dimethoxy-6H-benzo[b]chromin-6-one

8,9-dimethoxy-6H-benzo[b]chromin-6-one

Conditions
ConditionsYield
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

2,3-dimethoxy-1,3-butadiene

dimethyl L-tartrate
608-68-4

dimethyl L-tartrate

(2R,3R,5R,6R)-5,6-Dimethoxy-5-methyl-[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester

(2R,3R,5R,6R)-5,6-Dimethoxy-5-methyl-[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
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%

3588-31-6Relevant academic research and scientific papers

Synthesis of 2,3-substituted tetracenes and evaluation of their self-assembling properties in organic solvents

Reichwagen, Jens,Hopf, Henning,Del Guerzo, Andre,Belin, Colette,Bouas-Laurent, Henri,Desvergne, Jean-Pierre

, p. 971 - 974 (2005)

(Chemical Equation Presented) Rod-shaped 2,3-di-alkoxytetracenes, soluble in common organic solvents, have been synthesized and studied for their gelling ability in organic solvents and their unusual UV-visible spectroscopic properties.

A metal-free one-pot synthesis of benzo[: C] chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions

Zhang, Yan,Tian, Yan,Xiang, Pei,Huang, Ning,Wang, Jianyi,Xu, Jian-Hua,Zhang, Min

, p. 9874 - 9882 (2016)

An efficient, simple and versatile synthesis of biologically valuable benzo[c]chromen-6-ones is achieved using a tandem photo-thermal-photo reaction sequence starting from 3,4-dichlorocoumarins and a 1,3-butadiene. In this concise one-pot protocol, neither metal catalyst nor peroxide promoter is needed and the products can be purified through simple recrystallization in most cases. The synthesis consists of a reaction sequence of photo-induced [4 + 2] and [2 + 2] cycloadditions, silica gel promoted elimination of HCl and electrocyclic cyclobutene ring opening followed by a photo-induced 6π electrocyclization. The reactions proceed well with a range of dichlorocoumarins and some typical butadienes to provide the corresponding annulated products in 70-80% yield.

Attaching organic semiconductors to gate oxides: In situ assembly of monolayer field effect transistors

Tulevski, George S.,Miao, Qian,Fukuto, Masafumi,Abram, Rebecca,Ocko, Benjamin,Pindak, Ronald,Steigerwald, Michael L.,Kagan, Cherie R.,Nuckolls, Colin

, p. 15048 - 15050 (2004)

This study unveils a new tetracene derivative that forms dense, upright monolayers on the surface of aluminum oxide. These monolayers spontaneously self-organize into the active layer in nanoscale field-effect transistor devices when aluminum oxide is used as the dielectric layer. This method gives high yields of working devices that have source-drain distances that are less than 60 nm, thereby providing a method to electrically probe the monolayer assemblies formed from ~10 zeptomoles of material (approximately 104 molecules). Moreover, this study delineates a new avenue for research in thin-film organic transistors where the active molecules are linked to the dielectric surface to form a monolayer transistor. Copyright

Synthesis and activity of polyacetylene substituted 2-hydroxy acids, esters, and amides against microbes of clinical importance

Kyi, Stella,Wongkattiya, Nalin,Warden, Andrew C.,O'Shea, Michael S.,Deighton, Margaret,MacReadie, Ian,Graichen, Florian H.M.

supporting information; experimental part, p. 4555 - 4557 (2010/09/16)

A series of novel polyacetylene substituted 2-hydroxy acids and derivatives were prepared and characterized. Alkylation of butane-2,3-diacetal (BDA) protected glycolic acid with iodoalkyl substituted polyacetylene compounds gave the corresponding diacetal protected polyacetylene substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification or aminolysis afforded the 2-hydroxy-polyacetylenic acid, ester or amide derivatives. Twenty one of these novel compounds were tested against 10 microbes of clinical importance and several of them showed good antimicrobial activity, in particular against Pseudomonas aeruginosa.

CONJUGATED UNSATURATED COMPOUNDS

-

Page/Page column 49, (2009/10/22)

The present invention relates to a class of conjugated unsaturated compounds, to a method of preparing such compounds, and to the polymerisation and bio-active uses of such compounds including their use as antimicrobial agents. The invention particularly relates to compounds containing three conjugated unsaturated moieties, at least two of which are yne moieties.

ACETYLENIC COMPOUNDS

-

Page/Page column 60, (2008/06/13)

The present invention relates to a class of acetylenic compounds, to a method of preparing the acetylenic compounds, and to the polymerisation and therapeutic uses of the acetylenic compounds. The invention particularly relates to compounds containing two acetylenic moieties.

A new route to butane-1,2-diacetals and the development of alternative substitution patterns to facilitate differential protection of the products

Ley,Michel

, p. 1793 - 1795 (2007/10/03)

The utility of 2,3-dialkoxybutan-1,3-dienes as reagents for the protection of vicinal diols and α-hydroxy acids as their corresponding 1,2-diacetals is demonstrated together with their later deprotection under mild reaction conditions.

Different synthetic routes towards efficient organogelators: 2,3-substituted anthracenes

Pozzo, Jean-Luc,Clavier, Gilles M.,Colomes, Michel,Bouas-Laurent, Henri

, p. 6377 - 6390 (2007/10/03)

Three synthetic approaches towards 2,3-substituted anthracenes are reported and discussed in terms of selectivity and viability. This allowed us to introduce a variety of substituents as sidearms. Promising results have been found using a tandem Diels-Alder aromatization reaction using 2,2,3-dimethoxybuladiene 9 as a key intermediate. However, for multigram preparations the Friedel-Crafts approach is preferred.

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