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1,2-Dimethoxybenzene

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Name

1,2-Dimethoxybenzene

EINECS 202-045-3
CAS No. 91-16-7 Density 1.005 g/cm3
PSA 18.46000 LogP 1.70380
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 N/A Appearance clear colourless liquid after melting
Safety 36-23-24/25 Risk Codes 22-20/21/22
Molecular Structure Molecular Structure of 91-16-7 (1,2-Dimethoxybenzene) Hazard Symbols HarmfulXn
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;

Article Data 145

1,2-Dimethoxybenzene 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%

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/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

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: 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

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.

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