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91-16-7

Basic Information
CAS No.: 91-16-7
Name: 1,2-Dimethoxybenzene
Molecular Structure:
Molecular Structure of 91-16-7 (1,2-Dimethoxybenzene)
Formula: C8H10O2
Molecular Weight: 138.17
Synonyms: 2-Methoxyanisole;Benzene,1,2-dimethoxy-;1, 2-Dimethoxybenzene;Dimethylether pyrokatechinu [Czech];Catechol dimethyl ether;Veratrol;Benzene, 1, 2-dimethoxy-;Benzene, o-dimethoxy-;Pyrocatechol dimethyl ether;Benzene, 1,2-dimethoxy-;O,O-Dimethyl catechol;Brenzkatechindimethylether;Synthol;2-Dimethoxybenzol;o-Dimethoxybenzene;2-Dimethoxybenzene;1,2-Dimethoxybenzene;o-Dimethoxybenzene;Veratrole;Veratrole;1,2-dimethyocy benzene;
EINECS: 202-045-3
Density: 1.005 g/cm3
Melting Point: 15 °C(lit.)
Boiling Point: 206.3 °C at 760 mmHg
Flash Point: 76.6 °C
Solubility: slightly soluble in water
Appearance: clear colourless liquid after melting
Hazard Symbols: HarmfulXn
Risk Codes: 22-20/21/22
Safety: 36-23-24/25
Transport Information:
PSA: 18.46000
LogP: 1.70380
Synthetic route
120-80-9

benzene-1,2-diol

616-38-6

carbonic acid dimethyl ester

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In water at 0 - 100℃; for 7.5h; pH=8 - 9;99.3%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 160℃; under 15001.5 - 30003 Torr; for 8h; Temperature; Reagent/catalyst; Autoclave; Inert atmosphere;98.9%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 170℃; under 0 - 8250.83 Torr; for 0.333333h; Concentration; Reagent/catalyst; Solvent; Temperature; Time; Microwave irradiation;94.3%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 160℃; for 1h; Microwave irradiation; Green chemistry;90%
N,N,N',N'-tetrabutyl-N''-methylguanidine at 180℃; for 3h;70%
141077-52-3

3,4-dimethoxyphenyl trifluoromethanesulfonate

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With ammonium acetate; magnesium; palladium on activated charcoal In methanol at 20℃; for 1h;99%
With ammonium acetate; methanol; magnesium; palladium on activated charcoal at 20℃; for 1h;99%
With hydrogen; diethylamine; palladium on activated charcoal In methanol at 20℃; for 6h;89%
120-80-9

benzene-1,2-diol

74-88-4

methyl iodide

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
Stage #1: benzene-1,2-diol With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: methyl iodide In acetone at 20 - 60℃; Inert atmosphere;
98%
With potassium carbonate In acetone Heating;92%
With sodium hydroxide; Aliquat 336 In water for 1h; Heating;90%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 80℃; for 12h;84%
With potassium carbonate In acetone 1.) 5 min, reflux, 2.) 60 deg C, 5 h;
635-67-6

dimethyl phthalate

74-88-4

methyl iodide

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1.) 0 deg C, 1 h, 2.) 25 deg C;98%
67-56-1

methanol

529-28-2

4-iodoanisol

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With N,N-dimethylglycine hydrochoride; caesium carbonate; copper(l) iodide at 110℃; for 24h; Ullmann coupling reaction;98%
122775-35-3

3,4-Dimethoxyphenylboronic acid

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With acetic acid In 1,4-dioxane at 100℃; for 20h; Enzymatic reaction;97%
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In toluene at 70℃; for 1.5h; Solvent; Temperature; Reagent/catalyst; Microwave irradiation; Green chemistry;90%
With tetrafluoroboric acid; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); aniline; carbonic acid dimethyl ester; sodium nitrite In water at 20℃; for 0.266667h; Inert atmosphere; Schlenk technique; Irradiation;31 %Spectr.
90-05-1

2-methoxy-phenol

616-38-6

carbonic acid dimethyl ester

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 1.33333h; Microwave irradiation; Green chemistry;95%
With N-butyl-4-methylpyridinium bromide at 170℃; for 2h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction;75%
120-14-9

3,4-dimethoxy-benzaldehyde

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; Molecular sieve;93%
With rhodium(II) acetate; 1,3-bis-(diphenylphosphino)propane In toluene at 200℃; under 7500.75 Torr; Inert atmosphere;88%
With palladium nanoparticles deposited on porous SBA-15 In cyclohexane at 140℃; for 24h; Molecular sieve;85%
With sodium hydroxide; aluminum nickel at 90℃;
75-18-3

dimethylsulfide

90-05-1

2-methoxy-phenol

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
at 55℃;93%
120-80-9

benzene-1,2-diol

77-78-1

dimethyl sulfate

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;91%
Stage #1: benzene-1,2-diol With potassium carbonate In acetone for 0.25h;
Stage #2: dimethyl sulfate In acetone for 24h; Reflux;
90%
With potassium carbonate at 60℃; for 1h; Williamson synthesis;82%
84521-92-6

1-n-butoxy-2-(α,α-dimethoxypropionyl)cyclopropane

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.166667h; Heating;90%

erythro-1-(3,4-dimethoxyphenyl)-3,3-dimethyl-2-(2-methoxyphenoxy)-1,3-propanediol

616-38-6

carbonic acid dimethyl ester

A

91-16-7

1,2-dimethoxybenzene

B

2150-38-1

methyl 3,4-dimethoxybenzoate

Conditions
ConditionsYield
With caesium carbonate at 180℃; for 8h;A 88%
B 16%
90-05-1

2-methoxy-phenol

18107-18-1

diazomethyl-trimethyl-silane

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 16h; Ambient temperature;85%
2859-78-1

4-Bromoveratrole

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With isopropyl alcohol at 20℃; for 24h; UV-irradiation; chemoselective reaction;85%
With tetrabutylammonium tetrafluoroborate; triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 4.4h; Inert atmosphere; Electrolysis;82%
With 1,4-dioxane; 1,10-Phenanthroline; sodium hydride In mineral oil at 140℃; for 22h; Schlenk technique; Inert atmosphere;70%
5460-32-2

1-iodo-3,4-dimethoxybenzene

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;81%
67-56-1

methanol

321-28-8

1-fluoro-2-methoxybenzene

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 130℃; for 16h;79%
<(η-C6H6)(η-C5EtMe4)Rh>(2+)*2 In nitromethane at 80℃; for 96h;60 % Chromat.
101959-15-3

3,4-dimethoxyphenyl methanesulfonate

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With hydrogen; diethylamine; palladium on activated charcoal In methanol at 20℃; for 58h;79%
90-05-1

2-methoxy-phenol

77-78-1

dimethyl sulfate

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate at 50℃; for 1h; Williamson synthesis;78%
With sodium hydroxide
With potassium hydroxide at 90℃;
681-84-5

tetramethylorthosilicate

16463-34-6

potassium 2-methoxybenzoate

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 145℃; for 18h;78%
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 145℃; for 18h; Concentration; Chan-Lam Coupling; regioselective reaction;78%
37895-73-1

1,2-dibromo-4,5-dimethoxybenzene

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate; triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 4.4h; Inert atmosphere; Electrolysis;77%
120-80-9

benzene-1,2-diol

616-38-6

carbonic acid dimethyl ester

A

91-16-7

1,2-dimethoxybenzene

B

90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 170℃; under 0 - 8250.83 Torr; for 0.333333h; Concentration; Reagent/catalyst; Solvent; Microwave irradiation;A 76.8%
B 5.6%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 170℃; under 0 - 8250.83 Torr; for 0.333333h; Concentration; Reagent/catalyst; Solvent; Microwave irradiation;A 20.7%
B 36.2%
With calcined Mg/Al hydrotalcite (Mg/Al = 3) at 300℃; for 2h; Product distribution; Further Variations:; Temperatures; Methylation;
aluminium phosphate aluminium oxide catalyst at 299.85℃; Product distribution; Further Variations:; Catalysts; Temperatures;
6957-27-3

3,4-dihydropapaverine

A

15248-39-2

6,7-dimethoxyisoquinoline

B

91-16-7

1,2-dimethoxybenzene

C

58-74-2

Papaverine

Conditions
ConditionsYield
With Raney nickel at 130℃;A 5.8%
B 5.8%
C 76.2%
77-78-1

dimethyl sulfate

Amberlite IRA-400 catecholate dianion

Amberlite IRA-400 catecholate dianion

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
In methanol for 5h; Methylation;74%
90-05-1

2-methoxy-phenol

74-88-4

methyl iodide

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; Product distribution / selectivity;72%
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant;
150-76-5

4-methoxy-phenol

74-88-4

methyl iodide

91-16-7

1,2-dimethoxybenzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃;72%
120-80-9

benzene-1,2-diol

74-88-4

methyl iodide

A

91-16-7

1,2-dimethoxybenzene

B

90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With Aliquat; potassium hydrogencarbonate at 20℃; for 15h;A 13%
B 71%
122775-35-3

3,4-Dimethoxyphenylboronic acid

62-53-3

aniline

A

91-16-7

1,2-dimethoxybenzene

B

17423-55-1

3,4-dimethoxy-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: aniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1h;
Stage #2: 3,4-Dimethoxyphenylboronic acid With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In water; acetonitrile at 20℃; for 16h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Irradiation;
A n/a
B 70%
120-80-9

benzene-1,2-diol

77-78-1

dimethyl sulfate

A

91-16-7

1,2-dimethoxybenzene

B

90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With Aliquat; potassium hydrogencarbonate at 60℃; for 2h;A 2%
B 68%
With potassium hydroxide; Aliquat at 20℃; for 2h;A 24%
B 50%
2859-78-1

4-Bromoveratrole

25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

91-16-7

1,2-dimethoxybenzene

B

365564-10-9

2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,3-bis-(diphenylphosphino)propane; triethylamine In toluene at 100℃; for 18h; Inert atmosphere;A n/a
B 63%

erythro-1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diyldimethyl biscarbonate

A

91-16-7

1,2-dimethoxybenzene

B

2150-38-1

methyl 3,4-dimethoxybenzoate

Conditions
ConditionsYield
With caesium carbonate; carbonic acid dimethyl ester at 180℃; for 8h;A 62%
B 12%
91-16-7

1,2-dimethoxybenzene

709-09-1

3,4-dimethoxynitrobenzene

Conditions
ConditionsYield
With Nitrogen dioxide In dichloromethane in the dark; -78 deg C, 2 min; RT, 15 min;100%
With air; nitrogen(II) oxide In acetonitrile for 0.25h; Mechanism; Ambient temperature; other substituted anisoles;99%
With air; nitrogen(II) oxide In acetonitrile for 0.25h; Ambient temperature;99%
91-16-7

1,2-dimethoxybenzene

2859-78-1

4-Bromoveratrole

Conditions
ConditionsYield
With kaolin; sodium chlorite; manganese(III) acetylacetonate; sodium bromide In dichloromethane at 25℃; for 2h;100%
With N-Bromosuccinimide; (Z)-N-[3,5-bis(trifluoromethyl)phenyl]-4-(dimethyliminio)pyridine-1(4H)-carbimidothioate In dichloromethane at 0℃; for 36h; Darkness; regioselective reaction;99%
With N-Bromosuccinimide; silica gel In tetrachloromethane at 30℃; for 4h;98%
91-16-7

1,2-dimethoxybenzene

3395-03-7

4,5-dimethoxy-1,2-dinitrobenzene

Conditions
ConditionsYield
With nitric acid at 0 - 80℃; for 2h;100%
With nitric acid at 20℃;95%
With sulfuric acid; nitric acid94%
91-16-7

1,2-dimethoxybenzene

5460-32-2

1-iodo-3,4-dimethoxybenzene

Conditions
ConditionsYield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichloroiodate at 20℃; for 0.166667h;100%
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.4h; Heating;100%
With tetramethylammonium dibromoiodate(I) at 20℃; for 0.0833333h;100%
91-16-7

1,2-dimethoxybenzene

1711-05-3

m-anisoyl chloride

792-57-4

3,4-dimethoxy-3'-methoxybenzophenone

Conditions
ConditionsYield
aluminium trichloride In hexane; dichloromethane; ethyl acetate100%
With carbon disulfide; aluminium trichloride
91-16-7

1,2-dimethoxybenzene

98-88-4

benzoyl chloride

4038-14-6

3,4-dimethoxybenzophenone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate for 0.0833333h; Friedel-Crafts acylation; Ionic liquid; Microwave irradiation;100%
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 12h; Friedel-Crafts benzoylation;96%
Hf[N(SO2C8F17)2]4 In chlorobenzene at 110℃; for 1h;92%
91-16-7

1,2-dimethoxybenzene

123-38-6

propionaldehyde

140648-13-1

9,10-diethyl-2,3,6,7-tetramethoxy-anthracene

Conditions
ConditionsYield
With sulfuric acid; acetonitrile for 0.5h;100%
With sulfuric acid at 5 - 10℃;98%
With sulfuric acid In water at -10℃; for 2h;46%
91-16-7

1,2-dimethoxybenzene

2051-49-2

n-hexanoic anhydride

52375-87-8

1-(3,4-dimethoxyphenyl)-1-hexanone

Conditions
ConditionsYield
With gallium(III) trichloride; silver perchlorate In dichloromethane for 21h; Ambient temperature;100%
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Ambient temperature;94%
With antimonypentachloride; lithium perchlorate In dichloromethane for 0.5h; Heating;87%
diphenylboryl triflate In dichloromethane for 24h; Ambient temperature;81%
91-16-7

1,2-dimethoxybenzene

26429-16-3

trimethylsilyl pentanoate

66053-97-2

1-(3,4-dimethoxyphenyl) pentan-1-one

Conditions
ConditionsYield
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 20h; Ambient temperature;100%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 20h; Ambient temperature;100%
91-16-7

1,2-dimethoxybenzene

93-97-0

benzoic acid anhydride

4038-14-6

3,4-dimethoxybenzophenone

Conditions
ConditionsYield
With silver perchlorate; niobium pentachloride In nitromethane at 80℃; for 7h; Friedel-Crafts acylation;100%
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Ambient temperature;94%
Hf[N(SO2C8F17)2]4 In chlorobenzene at 110℃; for 2h;94%
91-16-7

1,2-dimethoxybenzene

98-88-4

benzoyl chloride

643-94-7

o-phenylene dibenzoate

Conditions
ConditionsYield
With hexabutylguanidium chloride hydrochloride In 1,2-dichloro-benzene for 0.833333h; microwave irradiation;100%
91-16-7

1,2-dimethoxybenzene

1066-45-1

trimethyltin(IV)chloride

134952-94-6

(2,3-dimethoxyphenyl)trimethylstannane

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane BuLi in hexane added to stirred soln. of veratrole and TMEDA in Et2O at 0°C, warmed to 22°C, stirred 1h, cooled to -80°C, addn. of (CH3)3SnCl in Et2O, warmed to 22°C, after 90 min H2O was added, stirred (room temp. overnight); Et2O layer washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure, distn. (Kugelrohr, 110°C, 0.04 mmHg); elem. anal.;;100%
91-16-7

1,2-dimethoxybenzene

108-12-3

isopentanoyl chloride

132858-47-0

1-(3,4-dimethoxyphenyl)-3-methylbutan-1-one

Conditions
ConditionsYield
Stage #1: isopentanoyl chloride With aluminum (III) chloride In dichloromethane at -4℃; for 0.0833333h; Friedel-Crafts Acylation; Inert atmosphere;
Stage #2: 1,2-dimethoxybenzene In dichloromethane at 0 - 4℃; for 1.25h; Friedel-Crafts Acylation; Inert atmosphere;
100%
Stage #1: isopentanoyl chloride With aluminum (III) chloride In dichloromethane for 0.166667h;
Stage #2: 1,2-dimethoxybenzene In dichloromethane for 0.166667h;
62.2%
Stage #1: isopentanoyl chloride With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,2-dimethoxybenzene In dichloromethane at 0℃; Inert atmosphere;
91-16-7

1,2-dimethoxybenzene

90076-65-6

bis(trifluoromethane)sulfonimide lithium

C18H20F6LiNO8S2

Conditions
ConditionsYield
at 20 - 150℃; Inert atmosphere;100%
91-16-7

1,2-dimethoxybenzene

7065-46-5

3,3-dimethylbutanoic acid chloride

1-(2',3'-dimethoxyphenyl)-3,3-dimethylbutan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;100%
91-16-7

1,2-dimethoxybenzene

4023-34-1

cyclopropanecarboxylic acid chloride

92847-88-6

cyclopropyl(3,4-dimethoxyphenyl)methanone

Conditions
ConditionsYield
Stage #1: cyclopropanecarboxylic acid chloride With aluminum (III) chloride In dichloromethane at -4℃; for 0.0833333h; Friedel-Crafts Acylation; Inert atmosphere;
Stage #2: 1,2-dimethoxybenzene In dichloromethane at -4 - 0℃; for 1.25h; Friedel-Crafts Acylation; Inert atmosphere;
100%
91-16-7

1,2-dimethoxybenzene

98-88-4

benzoyl chloride

92847-88-6

cyclopropyl(3,4-dimethoxyphenyl)methanone

Conditions
ConditionsYield
Stage #1: benzoyl chloride With aluminum (III) chloride In dichloromethane at -4℃; for 0.25h; Friedel-Crafts Acylation; Inert atmosphere;
Stage #2: 1,2-dimethoxybenzene In dichloromethane at -4 - 0℃; for 1.25h; Friedel-Crafts Acylation; Inert atmosphere;
100%
91-16-7

1,2-dimethoxybenzene

507-20-0

tertiary butyl chloride

41280-64-2

4-(tert-butyl)-1,2-dimethoxybenzene

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 22℃; for 0.166667h; Inert atmosphere;100%
91-16-7

1,2-dimethoxybenzene

1-azido-2-[(4-phenyl)buta-1,3-diyn-1-yl]benzene

C24H19NO2

Conditions
ConditionsYield
With [BrettPhosAu*MeCN]SbF6 for 27h; regioselective reaction;100%
91-16-7

1,2-dimethoxybenzene

629-72-1

pentadecyl bromide

7461-75-8

1,2-dimethoxy-3-pentadecyl-benzene

Conditions
ConditionsYield
Stage #1: 1,2-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 2h;
Stage #2: pentadecyl bromide In tetrahydrofuran; hexane at 210℃; for 5h;
99.7%
With n-butyllithium In tetrahydrofuran; hexane for 40h; Heating;2.7 g
91-16-7

1,2-dimethoxybenzene

37895-73-1

1,2-dibromo-4,5-dimethoxybenzene

Conditions
ConditionsYield
With bromine; iodine In dichloromethane for 3h;99.5%
With bromine In tetrachloromethane at 20℃; for 72h;99%
With oxygen; 1,2-dibromomethane at 50℃; for 1h;99%
91-16-7

1,2-dimethoxybenzene

75-36-5

acetyl chloride

1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With indium(III) tosylate In dodecane; nitromethane for 1h; Friedel-Crafts Acylation; Schlenk technique; Reflux;99%
With InIII-based[In(OTf)3] Polymeric Sulfonic Acid Catalyst In nitromethane for 2h; Reagent/catalyst; Friedel-Crafts Acylation; Schlenk technique; Reflux;80%
Stage #1: acetyl chloride With aluminum (III) chloride In dichloromethane at -5 - 0℃; for 0.583333h;
Stage #2: 1,2-dimethoxybenzene In dichloromethane at -5 - 0℃; for 1h;
75%
91-16-7

1,2-dimethoxybenzene

100-52-7

benzaldehyde

86467-27-8

1,2-dimethoxy-4-[(3,4-dimethoxyphenyl)-(phenyl)methyl]benzene

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 15h; Ambient temperature;99%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Friedel-Crafts Alkylation;95%
With Acetyl bromide; silica gel; zinc dibromide In benzene at 20℃; for 1h;94%
91-16-7

1,2-dimethoxybenzene

106372-59-2

ethyl 2-fluoro-2-(phenylsulfanyl)acetate

(3,4-dimethoxy-phenyl)-phenylsulfanyl-acetic acid ethyl ester

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 0.666667h;99%
91-16-7

1,2-dimethoxybenzene

126821-58-7

chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer

942477-65-8

[(η5-pentamethylcyclopentadienyl)Ru(η6-1,2-dimethoxybenzene)]Cl

Conditions
ConditionsYield
In water other Radiation; (N2); using Schlenk techniques; combining of C6H4(OMe)2 (8 equiv.), ((C5Me5)RuCl)4 (1 equiv.) and H2O in glass microwave reaction vessel with stir bar; sealing; microwave irradn. at 50 W (ca. 130°C for 10 min); evapn. of solvent under reduced pressure, extn., trituration with hexane; drying;99%
In water Sonication; (N2); using Schlenk techniques; combining of C6H4(OCH3)2 (8 equiv.), ((C5Me5)RuCl)4 (1 equiv.) and H2O in Schlenk tube with stir bar; sealing; heating in oil bath (ca. 115°C) with intermittent sonication for 1-3 ds; cooling to ca. 25°C; removal of solvent under reduced pressure; extn./trituration with toluene; drying;
91-16-7

1,2-dimethoxybenzene

64881-40-9

(3S)-3-methoxycarbonyl-3-trifluoroacetylaminopropanoyl chloride

1088806-69-2

methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-(2,2,2-trifluoroacetamido)butanoate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 0℃; for 1h; Friedel Crafts acylation; Neat (no solvent);99%
91-16-7

1,2-dimethoxybenzene

161553-08-8

(R)-N-trifluoroacetylaspartic acid-4-chloride-1-methyl ester

1088806-71-6

methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-(2,2,2-trifluoroacetamido)butanoate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 0℃; for 1h; Friedel Crafts acylation; Neat (no solvent);99%
91-16-7

1,2-dimethoxybenzene

1392407-17-8

1,3-diphenyl-3-(3,4-dimethoxyphenyl)-1-propene

Conditions
ConditionsYield
With silica gel supported sodium hydrogen sulfate In 1,2-dichloro-ethane at 30℃; for 0.5h; Friedel-Crafts type alkylation;99%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 20h; Friedel-Crafts Alkylation;79%
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Chemistry


IUPAC Name: 1,2-Dimethoxybenzene
Molecular Formula: C8H10O2
Molecular Weight: 138.16 g/mol
SMILES: c1(c(cccc1)OC)OC
InChI: InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
EINECS: 202-045-3
Product Categories: Aromatic Ethers; Benzene derivates
Melting Point: 15 °C(lit.)
Index of Refraction: 1.488 
Molar Refractivity: 39.6 cm3 
Molar Volume: 137.4 cm3 
Surface Tension: 29.6 dyne/cm 
Density: 1.005 g/cm
Flash Point: 87.2 °C 
Enthalpy of Vaporization: 42.44 kJ/mol 
Boiling Point: 206.3 °C at 760 mmHg 
Vapour Pressure of 1,2-Dimethoxybenzene (CAS NO.91-16-7): 0.344 mmHg at 25 °C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 700mg/kg (700mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(2), Pg. 54, 1982.
rat LD50 oral 890mg/kg (890mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(2), Pg. 54, 1982.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: HarmfulXn
Risk Statements: 22-20/21/22 
R22:Harmful if swallowed. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36-23-24/25 
S36:Wear suitable protective clothing. 
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS of 1,2-Dimethoxybenzene (CAS NO.91-16-7): CZ6475000

Specification

 1,2-Dimethoxybenzene (CAS NO.91-16-7), its Synonyms are Veratrole ; 2-Methoxyanisole ; Benzene, 1,2-dimethoxy- ; Benzene, o-dimethoxy- ; Brenzkatechindimethylether ; Catechol dimethyl ether ; Dimethylether pyrokatechinu ; O,O-Dimethyl catechol ; Pyrocatechol dimethyl ether . It is clear colourless liquid after melting. It is slightly soluble in water, but miscible in all organic solvents.