1,2-Dimethoxybenzene

Base Information

• Chemical Name: 1,2-Dimethoxybenzene
• CAS No.: 91-16-7
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Hs Code.: Oral rat LD50: 890 mg/kg
• European Community (EC) Number: 202-045-3
• NSC Number: 16934
• UNII: 61WJZ2Q41I
• DSSTox Substance ID: DTXSID7047065
• Nikkaji Number: J4.334F
• Wikipedia: 1,2-Dimethoxybenzene
• Wikidata: Q131994
• Pharos Ligand ID: 3L2K3D3YAR1P
• Metabolomics Workbench ID: 45287
• ChEMBL ID: CHEMBL1668603
• Mol file: 91-16-7.mol

Synonyms:1,2-dimethoxybenzene;o-dimethoxybenzene;veratrole

Chemical Property of 1,2-Dimethoxybenzene

Chemical Property:

• Appearance/Colour: clear colourless liquid after melting
• Vapor Pressure: 0.344mmHg at 25°C
• Melting Point: 15 °C(lit.)
• Refractive Index: n20/D 1.533(lit.)
• Boiling Point: 206.3 °C at 760 mmHg
• Flash Point: 76.6 °C
• PSA: 18.46000
• Density: 1.005 g/cm³
• LogP: 1.70380
• Storage Temp.: Store below +30°C.
• Solubility.: 6.69g/l insoluble
• Water Solubility.: Soluble in alcohol, diethyl ether, acetone, and methanol. Slightly soluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99% ^*data from raw suppliers

Veratrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36-23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC1=CC=CC=C1OC
• Description: 1, 2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is a colorless liquid with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol, too. 1, 2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase.1, 2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.
• Uses: 1, 2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. An example of the use of veratrole is in the synthesis of Domipizone. Veratrole can easily be brominated with NBS to give 4-bromoveratrole. Veratrole is common reagent in organic synthesis such as the synthesis of arizonins B1 and C1. Also used in the synthesis of pharmacophores of salmeterol and roflumilast as dual β2-adrenoreceptor agonists-PDE4 inhibitors. 1,2-Dimethoxybenzene was used to investigate the electroantennogram response of vine weevil, Otiorhynchus sulcatus to plant volatiles.

Technology Process of 1,2-Dimethoxybenzene

There total 136 articles about 1,2-Dimethoxybenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

4-Bromoveratrole (2859-78-1) → 1,2-dimethoxybenzene (91-16-7)

Guidance literature:

With isopropyl alcohol; at 20 ℃; for 24h; chemoselective reaction; UV-irradiation;

DOI:10.1039/C8CC08942F

Reference yield: 76.2%

3,4-dihydropapaverine (6957-27-3) → 6,7-dimethoxyisoquinoline (15248-39-2) + 1,2-dimethoxybenzene (91-16-7) + Papaverine (58-74-2)

Guidance literature:

With Raney nickel; at 130 ℃;

DOI:10.1134/S1070428020070258

Reference yield: 20.0%

2,3-dihydro-4H-1-benzopyran-4-one (491-37-2) + 3,4-Dimethoxyphenylboronic acid (122775-35-3) → 1-benzopyran-4(4H)-one (491-38-3) + 1,2-dimethoxybenzene (91-16-7) + 3',4'-dimethoxyflavanone (6344-21-4)

Guidance literature:

With [2,2]bipyridinyl; palladium(II) trifluoroacetate; oxygen; trifluoroacetic acid; In 1,4-dioxane; dimethyl sulfoxide; at 100 ℃; for 32h;

DOI:10.1021/acs.joc.9b01162

upstream raw materials:

benzoic acid methyl ester

potassium guaiacolate

phthalic acid dimethyl ester

carbonic acid-(2-methoxy-phenyl ester)-methyl ester

Downstream raw materials:

bis-(3,4-dimethoxy-phenyl)-phenyl-acetonitrile

3,4-dimethoxy-benzaldehyde

4-(4-hydroxy-3-methoxy-phenyl)-4-oxo-butyric acid

3-(3,4-dimethoxybenzoyl)propionic acid

Refernces

Facile total syntheses of idarubicinone-7-β-D-glucuronide: Convenient preparations of AB-ring synthon using some carboxylic acid derivatives

10.1081/SCC-120030758

The study presents a facile total synthesis of idarubicinone-7-β-D-glucuronide, an anthracycline antibiotic analog, using a series of carboxylic acid derivatives as key intermediates. The researchers employed polyphosphoric acid (PPA) and AlCl3 as catalysts to cyclize dimethoxybenzene with various carboxylic acid derivatives, yielding naphthalenones, which were further transformed into (+)-idarubicinone 3b. Esterification with (S)-(+)-O-acetylmandelic acid and subsequent separation and deprotection steps led to the isolation of (+)-3b and (2)-3b. These compounds were then glycosylated with acetobromo-α-D-glucuronic acid methyl ester, using ZnBr2 as a catalyst, to produce two kinds of idarubicinone-7-β-D-glucuronide (20 and 21). The synthesized compounds were intended to enhance drug efficacy, potentially improving the pharmacological profile of idarubicinone by attaching glucuronic acid moieties. The study also detailed the synthetic method for an AB-ring synthon necessary for the synthesis of the aglycone and provided a comprehensive analysis of the synthesized compounds using various analytical techniques.