1,2-Dimethoxybenzene supplier

Name
1,2-Dimethoxybenzene
EINECS 202-045-3
CAS No. 91-16-7
Article Data145
CAS DataBase
Density 1.005 g/cm³
Solubility slightly soluble in water
Melting Point 15 °C(lit.)
Formula C₈H₁₀O₂
Boiling Point 206.3 °C at 760 mmHg
Molecular Weight 138.166
Flash Point 76.6 °C
Transport Information
Appearance clear colourless liquid after melting
Safety 36-23-24/25
Risk Codes 22-20/21/22
Molecular Structure
Hazard Symbols Xn
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 55℃;	93%

: 120-80-9
benzene-1,2-diol

: 77-78-1
dimethyl sulfate

: 91-16-7
1,2-dimethoxybenzene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With caesium carbonate at 180℃; for 8h;	A 88% B 16%

...Expand

: 90-05-1
2-methoxy-phenol

: 18107-18-1
diazomethyl-trimethyl-silane

: 91-16-7
1,2-dimethoxybenzene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
With Raney nickel at 130℃;	A 5.8% B 5.8% C 76.2%

...Expand

: 77-78-1
dimethyl sulfate

Amberlite IRA-400 catecholate dianion: Amberlite IRA-400 catecholate dianion

: 91-16-7
1,2-dimethoxybenzene

Conditions

Conditions	Yield
In methanol for 5h; Methylation;	74%

: 90-05-1
2-methoxy-phenol

: 74-88-4
methyl iodide

: 91-16-7
1,2-dimethoxybenzene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With Aliquat; potassium hydrogencarbonate at 20℃; for 15h;	A 13% B 71%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
With Aliquat; potassium hydrogencarbonate at 60℃; for 2h;	A 2% B 68%
With potassium hydroxide; Aliquat at 20℃; for 2h;	A 24% B 50%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With nitric acid at 0 - 80℃; for 2h;	100%
With nitric acid at 20℃;	95%
With sulfuric acid; nitric acid	94%

: 91-16-7
1,2-dimethoxybenzene

: 5460-32-2
1-iodo-3,4-dimethoxybenzene

Conditions

Conditions	Yield
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

Conditions	Yield
aluminium trichloride In hexane; dichloromethane; ethyl acetate	100%
With carbon disulfide; aluminium trichloride

: 91-16-7
1,2-dimethoxybenzene

: 98-88-4
benzoyl chloride

: 4038-14-6
3,4-dimethoxybenzophenone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trifluorormethanesulfonic acid at 0℃; for 1h; Friedel Crafts acylation; Neat (no solvent);	99%

: 91-16-7
1,2-dimethoxybenzene

: 4663-33-6, 62668-02-4, 62839-70-7, 116127-91-4, 132014-29-0, 136981-81-2, 148616-45-9
1,3-diphenyl-3-hydroxypropene

: 1392407-17-8
1,3-diphenyl-3-(3,4-dimethoxyphenyl)-1-propene

Conditions

Conditions	Yield
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%

1,2-Dimethoxybenzene Chemical Properties

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/cm³
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

1,2-Dimethoxybenzene 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.

1,2-Dimethoxybenzene Consensus Reports

Reported in EPA TSCA Inventory.

1,2-Dimethoxybenzene Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Harmful Xn
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

1,2-Dimethoxybenzene 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.

Product Name

1,2-Dimethoxybenzene

Synthetic route

1,2-Dimethoxybenzene Chemical Properties

1,2-Dimethoxybenzene Toxicity Data With Reference

1,2-Dimethoxybenzene Consensus Reports

1,2-Dimethoxybenzene Safety Profile

1,2-Dimethoxybenzene Specification

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