4,6-Dimethoxysalicylaldehyde

Base Information

• Chemical Name: 4,6-Dimethoxysalicylaldehyde
• CAS No.: 708-76-9
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 2912499000
• European Community (EC) Number: 211-904-1
• UNII: 8AQ22EXM7G
• DSSTox Substance ID: DTXSID3022110
• Nikkaji Number: J193.077J
• Wikidata: Q72468582
• ChEMBL ID: CHEMBL3660367
• Mol file: 708-76-9.mol

Synonyms:4,6-Dimethoxysalicylaldehyde;708-76-9;2-Hydroxy-4,6-dimethoxybenzaldehyde;4,6-Dimethoxy-2-hydroxybenzaldehyde;Benzaldehyde, 2-hydroxy-4,6-dimethoxy-;2,4-Dimethoxy-6-hydroxybenzaldehyde;EINECS 211-904-1;MFCD00003328;8AQ22EXM7G;2-formyl-3,5-dimethoxyphenol;2-hydroxy-4,6-bis(methyloxy)benzaldehyde;UNII-8AQ22EXM7G;SCHEMBL829755;CHEMBL3660367;DTXSID3022110;BDBM111035;AMY31146;4,6-Dimethoxysalicylaldehyde, 98%;4,6-dimethoxy-2-hydroxy-benzaldehyde;AKOS009156386;CS-W005297;SALICYLALDEHYDE, 4,6-DIMETHOXY-;AC-30645;AS-11337;BP-10727;SY027374;LS-184895;A9318;D4165;FT-0632859;EN300-193140;10.14272/FQRQWPNYJOFDLO-UHFFFAOYSA-N.1;doi:10.14272/FQRQWPNYJOFDLO-UHFFFAOYSA-N.1;J-514163;US8614253, .3-66;Z1255464954

Chemical Property of 4,6-Dimethoxysalicylaldehyde

Chemical Property:

• Appearance/Colour: yellow to beige crystalline powder
• Vapor Pressure: 4.9E-05mmHg at 25°C
• Melting Point: 68-70 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 338.8 °C at 760 mmHg
• PKA: 7.42±0.15(Predicted)
• Flash Point: 138 °C
• PSA: 55.76000
• Density: 1.234
• LogP: 1.22190
• Storage Temp.: Store Cold
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 171

Purity/Quality:

98% ^*data from raw suppliers

4,6-Dimethoxysalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)OC)C=O)O
• Uses: 4,6-Dimethoxysalicylaldehyde was used in the preparation of a new class of efficient ketocoumarin triplet sensitizers. It was used as staring reagent in the total synthesis of (+/-)-linderol A, a hexahydrodibenzofuran.

Technology Process of 4,6-Dimethoxysalicylaldehyde

There total 30 articles about 4,6-Dimethoxysalicylaldehyde 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: 94.0%

formic acid 3,5-dimethoxy-phenyl ester → 2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9)

Guidance literature:

With boron trichloride; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1515/znb-2001-1113

Reference yield: 74.0%

2,4,6-trihydroxybenzaldehyde (487-70-7) + methyl iodide (74-88-4) → 2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9)

Guidance literature:

2,4,6-trihydroxybenzaldehyde; With potassium carbonate; In acetone; Heating;

methyl iodide; In acetone; for 3h; Further stages.;

DOI:10.1016/j.bmcl.2007.04.018

Reference yield: 72.0%

2,4,6-trihydroxybenzaldehyde (487-70-7) + dimethyl sulfate (77-78-1) → 2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.5b02076

upstream raw materials:

diazomethane

2,4,6-trihydroxybenzaldehyde

2,4-dihydroxy-6-methoxybenzaldehyde

3,5-dimethoxyphenol

Downstream raw materials:

2-((Z)-2-hydroxy-4,6-dimethoxy-benzylidene)-6-methoxy-benzofuran-3-one

Limettin

2-acetoxy-4,6-dimethoxy-benzaldehyde

2-ethoxycarbonylmethoxy-4,6-methoxybenzaldehyde

Refernces

• 1、 Giurg, Miros?aw,Maniak, Halina,Matyja, Konrad,Talma, Micha?,Trusek, Anna. "Synthesis and structure-activity relationship studies of hydrazide-hydrazones as inhibitors of laccase from trametes versicolor". . . Retrieved 2020/03/23.
• 2、 Aucamp, Janine,Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre'Blanche, Gisella. "Synthesis and evaluation of methoxy substituted 2-benzoyl-1-benzofuran derivatives as lead compounds for the development adenosine A1 and/or A2A receptor antagonists". . . Retrieved 2019/12/25.