5556-86-5

Basic information

• Product Name: 2,3,6-trimethoxybenzaldehyde
• Synonyms: 2,3,6-Trimethoxybenzaldehyde
• CAS NO: 5556-86-5
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.1999
• EINECS: 226-918-3
• Mol File: 5556-86-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 327.4°C at 760 mmHg
• Flash Point: 145.2°C
• Density: 1.133g/cm³
• Vapor Pressure: 0.000203mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: 2,3,6-trimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-trimethoxybenzaldehyde(5556-86-5)
• EPA Substance Registry System: 2,3,6-trimethoxybenzaldehyde(5556-86-5)

Safety Data

• Hazardous Substances Data: 5556-86-5(Hazardous Substances Data)

Usage

General Description

2,3,6-Trimethoxybenzaldehyde, also known as TMB or 2,3,6-trimethoxybenzaldehyde, is a chemical compound with the formula C10H12O4. It is a colorless to pale yellow liquid with a sweet, floral odor, and is commonly used as a flavor and fragrance ingredient in the food and perfume industries. TMB has several industrial applications, including as a key intermediate in the production of pharmaceuticals, pesticides, and other organic compounds. It is valued for its ability to impart a pleasant aroma and taste to various products and is also used as a chemical building block in organic synthesis. Additionally, TMB has been studied for its potential biological and pharmacological properties, with research suggesting that it may have antioxidant and anti-inflammatory effects. Overall, 2,3,6-Trimethoxybenzaldehyde is a versatile compound with diverse industrial and potential medicinal applications.

Upstream product

• 67-56-1 methanol 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 1104548-55-1 2,3,6-trimethoxybenzyl alcohol 
• 108249-39-4 3-formyl-2,5-dihydroxy-4-methoxy-benzoic acid 
• 99513-28-7 3-formyl-2-hydroxy-4-methoxy-benzoic acid 
• 39503-30-5 3-formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 68-12-2 N,N-dimethyl-formamide 
• 80832-56-0 3,6-dihydroxy-2-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 326606-12-6 2,3,6-trimethoxy-5-nitrobenzaldehyde 
• 5556-80-9 1-(2,3,6-Trimethoxyphenyl)-2-nitropropene 
• 1217503-45-1 (1E,4E)-1,5-bis(2,3,6-trimethoxyphenyl)penta-1,4-dien-3-one 
• 1104548-55-1 2,3,6-trimethoxybenzyl alcohol 
• 15806-31-2 2,3,6-trimethoxy-phenethylamine 
• 326606-26-2 (3S,5S,6S)-3-[(1S,3R)-1-methoxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one 
• 326606-17-1 (3S,5S,6S)-3-[(1S,3R)-1-methoxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-ol 
• 326606-16-0 (3S,5S,6S)-3-[(1S,3R)-1-hydroxy-3-methyl-4-(5-nitro-2,3,6-trimethoxy-phenyl)-butyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one 
• 326606-09-1 (4R,5S,7R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-7-methyl-8-(5-nitro-2,3,6-trimethoxy-phenyl)-oct-2-enoic acid methyl ester 
• 326606-21-7 (2R,3S,5R)-3-methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexan-1-ol 
• 326606-14-8 (4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one 
• 326606-22-8 (2S,3S,5R)-3-Methoxy-2-(2-methoxy-ethoxymethoxy)-5-methyl-6-(2,3,6-trimethoxy-5-nitro-phenyl)-hexanal 

Relevant articles and documents

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

Synthesis of 1,2,4-trimethoxybenzene and its selective functionalization at C-3 by directed metalation

A new and efficient strategy was developed for the preparation of 1,2,4-trimethoxybenzene (3, a powerful attractant of Euglossini bees) and its C-3 derivatives (7a-j), from vanillin (2) in 56% overall yield.

Total syntheses of new proansamitocin derivatives by ring-closing metathesis

The enantioselective synthesis of two new proansamitocin derivatives is described. Macrocyclization is achieved by ring-closing metathesis of appropriate alkene and diene precursors. Georg Thieme Verlag Stuttgart.