2,6-Dimethoxybenzaldehyde

Base Information

• Chemical Name: 2,6-Dimethoxybenzaldehyde
• CAS No.: 3392-97-0
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29124990
• European Community (EC) Number: 919-150-1,625-546-2
• NSC Number: 72362
• UNII: 54P7CG8V99
• DSSTox Substance ID: DTXSID80187545
• Nikkaji Number: J185.772J
• Wikidata: Q27261228
• Mol file: 3392-97-0.mol

Synonyms:NSC 72362;

Chemical Property of 2,6-Dimethoxybenzaldehyde

Chemical Property:

• Appearance/Colour: yellow to beige crystalline powder
• Vapor Pressure: 0.00217mmHg at 25°C
• Melting Point: 96-98 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 289.6 °C at 760 mmHg
• Flash Point: 119.8 °C
• PSA: 35.53000
• Density: 1.114 g/cm³
• LogP: 1.51630
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Soluble in Methanol (almost transparency).
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethoxybenzaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC=C1)OC)C=O
• Uses: 2,6-Dimethoxybenzaldehyde is a widely used reactant that has been used in the synthesis of thiazolidin-4-one derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors. 2,6-Dimethoxybenzaldehyde has been used in the preparation of 2,6-dihydroxybenzaldehyde by demethylation with AlBr3.

Technology Process of 2,6-Dimethoxybenzaldehyde

There total 39 articles about 2,6-Dimethoxybenzaldehyde 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: 90.0%

2,6-dimethoxybenzaldehyde oxime → 2,6-dimethoxybenzaldehyde (3392-97-0)

Guidance literature:

With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; tetrabutylammonium periodite; In dichloromethane; for 2.5h; Product distribution; Ambient temperature; other oximes and hydrazones; also NaIO₄ and tetrabutylammonium bromide as reagents; var. time and solvents;

DOI:10.1039/a802186d

Reference yield: 89.0%

2,6-dimethoxybenzyl alcohol (16700-55-3) → 2,6-dimethoxybenzaldehyde (3392-97-0)

Guidance literature:

With dipotassium peroxodisulfate; at 40 ℃; for 0.0833333h; Ionic liquid;

DOI:10.1080/00397910802374117

Reference yield: 86.0%

2-6-dimethoxybenzoic acid (1466-76-8) → 2,6-dimethoxybenzaldehyde (3392-97-0)

Guidance literature:

With 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C₂₀]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine; In toluene; for 24h; Irradiation;

DOI:10.1021/acscatal.8b03592

upstream raw materials:

(2,6-dimethoxy-phenyl)-glyoxylic acid

(E)-1,3-dimethoxy-2-(prop-1-en-1-yl)benzene

2,6-dihydroxybenzaldehyde

dimethyl sulfate

Downstream raw materials:

(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-phenyl)-acetonitrile

2-(2,6-dimethoxyphenyl)benzothiazoline

Refernces

• 1、 Tangestaninejad, Shahram,Habibi, Mohammad Hossein,Iravani, Mohammad Reza. "Efficient and Mild Regeneration of Carbonyl Compounds from Oximes and Hydrazones by Manganese(III) Porphyrin-Periodate". . p. 456 - 457. Retrieved 1998.
• 2、 Bellière-Baca, Virginie,Clavier, Hervé,Hérault, Damien,Massouh, Joe,Petrelli, Antoine. "Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis". supporting information. . Retrieved 2022/01/06.
• 3、 Stache, Erin E.,Ertel, Alyssa B.,Rovis, Tomislav,Doyle, Abigail G.. "Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds". . p. 11134 - 11139. Retrieved 2018/11/21.