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| CAS No.: | 91-16-7 |
|---|---|
| Name: | 1,2-Dimethoxybenzene |
| Article Data: | 145 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H10O2 |
| Molecular Weight: | 138.166 |
| 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: |
 Xn
|
| Risk Codes: | 22-20/21/22 |
| Safety: | 36-23-24/25 |
| PSA: | 18.46000 |
| LogP: | 1.70380 |
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| 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% |
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1,2-dimethoxybenzene
| 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% |
| 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; |
| 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% |
| Conditions | Yield |
|---|---|
| With N,N-dimethylglycine hydrochoride; caesium carbonate; copper(l) iodide at 110℃; for 24h; Ullmann coupling reaction; | 98% |
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- 91-16-7
1,2-dimethoxybenzene
| 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. |
| 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% |
| 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℃; |
| Conditions | Yield |
|---|---|
| at 55℃; | 93% |
| 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% |
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Chemistry
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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
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: 
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
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.