2,6-Dimethoxyphenol

Base Information

• Chemical Name: 2,6-Dimethoxyphenol
• CAS No.: 91-10-1
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: 29095090
• European Community (EC) Number: 202-041-1
• UNII: 4UQT464H8K
• DSSTox Substance ID: DTXSID2052607
• Nikkaji Number: J27.321J
• Wikipedia: Syringol
• Wikidata: Q421420
• Metabolomics Workbench ID: 46389
• ChEMBL ID: CHEMBL109652
• Mol file: 91-10-1.mol

Synonyms:2,6-dimethoxyphenol;pyrogallol 1,3-dimethyl ether;Syringol

Chemical Property of 2,6-Dimethoxyphenol

Chemical Property:

• Appearance/Colour: off-white or grey to brown crystalline powder
• Vapor Pressure: 0.00591mmHg at 25°C
• Melting Point: 50-57 °C(lit.)
• Refractive Index: 1.522
• Boiling Point: 264.5 °C at 760 mmHg
• PKA: 9.97±0.10(Predicted)
• Flash Point: 99.9 °C
• PSA: 38.69000
• Density: 1.134 g/cm³
• LogP: 1.40940
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: 2 g/100 mL (13 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 104

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethoxyphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: COC1=C(C(=CC=C1)OC)O
• Uses: 2,6-Dimethoxyphenol has been used as a metabolite of lignin depolymerisation.It is also used as flavoring agent or adjuvant.It is reported to be the single most important flavor chemical in smoke flavors. It is used in smoke flavors, whisky, rum, tea, spice, savory, seafood, meat, liquorices, coffee, and nut flavors.

Technology Process of 2,6-Dimethoxyphenol

There total 154 articles about 2,6-Dimethoxyphenol 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: 99.0%

2-(2,6-dimethoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one (140455-39-6) → 1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With oxygen; copper(II) nitrate; In acetonitrile; at 120 ℃; for 10h; under 4500.45 Torr;

Reference yield: 92.0%

2-(2,6-dimethoxyphenoxy)-1-phenylethan-1-ol (145804-82-6) → 1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + ethylbenzene (100-41-4,27536-89-6) + rac-1-cyclohexylethanol (1193-81-3)

Guidance literature:

With Ni_0.85Ru_0.15; hydrogen; In water; at 95 ℃; for 16h; under 760.051 Torr; Reagent/catalyst;

DOI:10.1039/c8sc00742j

Reference yield: 83.0%

2-(2,6-dimethoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one (140455-39-6) → 1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With formic acid; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere; Irradiation;

DOI:10.1021/acscatal.7b01010

upstream raw materials:

methyl magnesium iodide

1,2,3-trimethoxybenzene

3,5-dimethoxy-4-hydroxybenzoic acid

3,4,5-trimethoxybenzoic acid methyl ester

Downstream raw materials:

syringic alcohol

2,6-dimethoxyphenyl benzoate

3-hydroxy-2,4-dimethoxy-benzophenone

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

Refernces

• 1、 Maksyutina. "". . . Retrieved 1975.
• 2、 Chen, Changzhou,Jiang, Jianchun,Li, Jing,Liu, Peng,Wu, Dichao,Xia, Haihong,Zhou, Minghao. "Eco-friendly preparation of ultrathin biomass-derived Ni3S2-doped carbon nanosheets for selective hydrogenolysis of lignin model compounds in the absence of hydrogen". . p. 3090 - 3103. Retrieved 2021/05/07.
• 3、 Fang, Zhen,Flynn, Michael G.,Jackson, James E.,Hegg, Eric L.. "Thio-assisted reductive electrolytic cleavage of lignin β-O-4 models and authentic lignin". supporting information. p. 412 - 421. Retrieved 2021/01/28.