29865-90-5

Basic information

• Product Name: 3,4-Dimethoxy-5-hydroxybenzaldehyde
• Synonyms: 5-Hydroxyveratraldehyde, 2,3-Dimethoxy-5-formylphenol;258717_ALDRICH;FR-2371;InChI=1/C9H10O4/c1-12-8-4-6(5-10)3-7(11)9(8)13-2/h3-5,11H,1-2H;3-HYDROXY-4,5-DIMETHOXYBENZALDEHYDE;5-HYDROXY-VERATRALDEHYDE;3,4-DIMETHOXY-5-HYDROXYBENZALDEHYDE;Benzaldehyde, 3-hydroxy-4,5-dimethoxy-
• CAS NO: 29865-90-5
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde
• Mol File: 29865-90-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 67-69°C
• Boiling Point: 177-180°C
• Flash Point: 133.4°C
• Appearance: /
• Density: 1.2481 (rough estimate)
• Vapor Pressure: 0.000259mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 8.87±0.15(Predicted)
• CAS DataBase Reference: 3,4-Dimethoxy-5-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxy-5-hydroxybenzaldehyde(29865-90-5)
• EPA Substance Registry System: 3,4-Dimethoxy-5-hydroxybenzaldehyde(29865-90-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 29865-90-5(Hazardous Substances Data)

Usage

Uses

5-Hydroxy-3,4-dimethoxybenzaldehyde is a useful synthetic intermediate. It was used in the synthesis of aryl benzothiazole derivatives with antitumor activities or as potential PET cancer imaging agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1941, 1983 DOI: 10.1021/jo00160a001

InChI:InChI=1/C9H10O4/c1-12-8-4-6(5-10)3-7(11)9(8)13-2/h3-5,11H,1-2H3

Upstream product

• 109566-96-3 N-benzenesulfonyl-N'-(3,4-dimethoxy-5-methoxycarbonyloxy-benzoyl)-hydrazine 
• 22675-96-3 2-methoxyphenoxy-3',4'-dimethoxyacetophenone 
• 71295-21-1 5-bromo-2,3-dimethoxybenzaldehyde 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 111786-43-7 3-Hydroxy-4,5-dimethoxy-benzonitrile 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 3934-87-0 5-hydroxyvanillin 
• 74-88-4 methyl iodide 
• 121-33-5 vanillin 
• 77-78-1 dimethyl sulfate 
• 854872-79-0 3,4-dimethoxy-5-methoxycarbonyloxy-benzoic acid 
• 1916-08-1 3-hydroxy-4,5-dimethoxybenzoic acid 
• 93828-11-6 1-bromo-3-hydroxy-4,5-dimethoxybenzene 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 

Downstream Products

• 101569-51-1 4-(5-formyl-2,3-dimethoxy-phenoxy)-3-nitro-benzoic acid methyl ester 
• 916606-30-9 6-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole 
• 1025906-30-2 3-(3-benzyloxy-4,5-dimethoxy-benzyl)-4-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2-one 
• 1155263-42-5 5-(4H-benzo[d][1,3]dithiin-2-yl)-2,3-dimethoxyphenol 
• 1351593-99-1 3,4-dimethoxy-5-(2,2,2-trifluoroethoxy)benzaldehyde 
• 75287-20-6 3-ethoxy-4,5-dimethoxybenzaldehyde 
• 1351593-96-8 3-isobutoxy-4,5-dimethoxybenzaldehyde 
• 912957-28-9 Viscolin 
• 1357024-86-2 (E)-3-(4-(benzyloxy)-2,3,6-trimethoxyphenyl)-1-(4-(benzyloxy)-3-methoxyphenyl)-prop-2-en-1-one 
• 1357024-85-1 2-(benzyloxy)-3,4,6-trimethoxybenzaldehyde 
• 52249-82-8 4-(benzyloxy)-2,3,6-trimethoxybenzaldehyde 
• 855242-15-8 1-(benzyloxy)-2,3,5-trimethoxybenzene 
• 1392322-55-2 1-isopropoxy-4-(3-(4-isopropoxy-3-methoxyphenyl)propyl)-2,3,5-trimethoxybenzene 
• 1392322-52-9 1-isopropoxy-2,3,5-trimethoxybenzene 

Relevant articles and documents

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Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine

A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.

An efficient synthesis of a potent anti-inflammatory agent, viscolin, and its inducible nitric oxide synthase inhibitory activity

A new and efficient synthetic pathway employed the aldol condensation between the acetophenone (3) and vanillin derivative (4) resulted in the precursor chalcone intermediate (14). The target compound viscolin (1) could be afforded through the hydrogenation of the chalcone and followed by deprotection. The present strategy described the development of a more efficient procedure that allowed large-scale production of viscolin for the further research of biological activity both in vitro and in vivo.