7083-19-4

Basic information

• Product Name: 2-METHOXY-5-METHYLBENZALDEHYDE
• Synonyms: 2-Methoxy-5-methylbenzaldehyde; 5-Methyl-o-anisaldehyde; Benzaldehyde, 2-methoxy-5-methyl-; VHR C1 FO1 [WLN]
• CAS NO: 7083-19-4
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.18
• Mol File: 7083-19-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 252.6°C at 760 mmHg
• Flash Point: 110.4°C
• Appearance: /
• Density: 1.08
• Vapor Pressure: 0.0192mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-METHOXY-5-METHYLBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-5-METHYLBENZALDEHYDE(7083-19-4)
• EPA Substance Registry System: 2-METHOXY-5-METHYLBENZALDEHYDE(7083-19-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7083-19-4(Hazardous Substances Data)

Usage

General Description

2-METHOXY-5-METHYLBENZALDEHYDE, also known as O-TOLUALDEHYDE, is a chemical compound with the molecular formula C9H10O2. It is a pale yellow liquid with a sweet, floral odor, commonly used in the production of fragrances and flavorings. O-TOLUALDEHYDE is also used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is a versatile chemical with applications in various industries, including cosmetics, food, and pharmaceuticals. However, it should be handled with caution as it can be a skin and eye irritant and may be harmful if swallowed or inhaled.

InChI:InChI=1/C9H10O2/c1-7-3-4-9(11-2)8(5-7)6-10/h3-6H,1-2H3

Upstream product

• 104-93-8 p-methylanizole 
• 74-90-8 hydrogen cyanide 
• 68-12-2 N,N-dimethyl-formamide 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 
• 7048-40-0 (2-methoxy-5-methylphenyl)methanol 
• 74-88-4 methyl iodide 
• 22002-45-5 2-bromo-4-methylanisole 
• 63113-79-1 methyl 2-methoxy-5-methylbenzoate 
• 4885-02-3 Dichloromethyl methyl ether 
• 67-56-1 methanol 
• 620-23-5 m-tolyl aldehyde 

Downstream Products

• 103203-48-1 4-methyl-2-(trans-2-nitro-vinyl)-anisole 
• 705288-17-1 2-methoxy-5-methyl-mandelonitrile 
• 6738-23-4 2,4-dimethylanisole 
• 2206-43-1 4-methoxyisophthalic acid 
• 861518-39-0 2,2'-Dimethoxy-5,5'-dimethyl-benzil 
• 103986-76-1 (E)-3-(2-methoxy-5-methylphenyl)propenoic acid 
• 858786-32-0 3-hydroxy-3-(2-methoxy-5-methyl-phenyl)-propionic acid ethyl ester 
• 22538-86-9 (2-methoxy-5-methyl-benzyliden)-aniline 
• 82129-31-5 2-(2-methoxy-5-methylphenyl)-2-trimethylsiloxyethanenitrile 
• 130633-08-8 1-(2'-methoxy-5'-methylphenyl)-2-methylpropan-1-ol 
• 139548-19-9 5-Ethyl-3-(2-methoxy-5-methyl-benzylamino)-6-methyl-1H-pyridin-2-one 
• 22538-86-9 (E)-2-Methoxy-4-methyl-N-phenylbenzaldimin 
• 25045-36-7 2-methoxy-5-methylbenzoic acid 
• 107274-42-0 2-methoxy-5-methyl-cinnamic acid ethyl ester 

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.

Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite

A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation- protodeboronation methodology

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation-protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.