37934-89-7

Basic information

• Product Name: 2,6-DIMETHYL-4-METHOXYBENZOIC ACID
• Synonyms: 2,6-DIMETHYL-4-METHOXYBENZOIC ACID;4-METHOXY-2,6-DIMETHYLBENZOIC ACID
• CAS NO: 37934-89-7
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Mol File: 37934-89-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 144.5-145 °C
• Boiling Point: 310 °C at 760 mmHg
• Flash Point: 121.7 °C
• Appearance: /
• Density: 1.136 g/cm³
• Vapor Pressure: 0.000266mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.98±0.37(Predicted)
• CAS DataBase Reference: 2,6-DIMETHYL-4-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYL-4-METHOXYBENZOIC ACID(37934-89-7)
• EPA Substance Registry System: 2,6-DIMETHYL-4-METHOXYBENZOIC ACID(37934-89-7)

Safety Data

• Hazardous Substances Data: 37934-89-7(Hazardous Substances Data)

Usage

General Description

2,6-DIMETHYL-4-METHOXYBENZOIC ACID, also known as p-methoxysalicylic acid, is a chemical compound with the molecular formula C10H12O4. It is a derivative of salicylic acid and is commonly used as a sunscreen agent due to its ability to absorb UVB radiation. It is a white or off-white crystalline powder with a slightly bitter taste and is soluble in organic solvents. 2,6-DIMETHYL-4-METHOXYBENZOIC ACID is also used in the manufacture of pharmaceuticals, fragrances, and as a flavoring agent in the food industry. It has anti-inflammatory and analgesic properties, making it a valuable ingredient in topical pain relief products. Additionally, it is used in the synthesis of various organic compounds in the chemical industry.

InChI:InChI=1/C10H12O3/c1-6-4-8(13-3)5-7(2)9(6)10(11)12/h4-5H,1-3H3,(H,11,12)

Upstream product

• 6267-34-1 2-bromo-5-methoxy-1,3-dimethyl-benzene 
• 31247-59-3 2,6-dimethyl-4-methoxybenzoyl chloride 
• 21971-21-1 2-chloro-4-methoxybenzoic acid 
• 75-24-1 trimethylaluminum 
• 124-38-9 carbon dioxide 
• 28636-93-3 2,6-dimethyl-4-hydroxybenzyl alcohol 
• 70547-87-4 2,6-dimethyl-4-hydroxybenzaldehyde 
• 19447-00-8 4-methoxy-2,6-dimethylbenzylaldehyde 
• 67-64-1 acetone 
• 87513-49-3 2,4-dinitrophenyl 4-methoxy-2,6-dimethylbenzoate 
• 34743-49-2 4-methoxy-2,6-dimethylaniline 
• 61000-21-3 (4-methoxy-2,6-dimethylphenyl)methanol 

Downstream Products

• 31247-59-3 2,6-dimethyl-4-methoxybenzoyl chloride 
• 75056-97-2 2,6-dimethyl-4-hydroxybenzoic acid 
• 114820-17-6 4-methoxy-2,6-dimethyl-benzoic acid amide 
• 1239952-30-7 [2-(4-methoxy-2,6-dimethylbenzoyl)-2,3-dihydro-1H-isoindol-5-yl]-(9-pyridin-4-yl-3,9-diazaspiro[5.5]undecan-3-yl)methanone 
• 153968-41-3 (4-Methoxy-2,6-dimethyl-benzoyl)-phosphonic acid diethyl ester 
• 34743-49-2 4-methoxy-2,6-dimethylaniline 
• 87513-49-3 2,4-dinitrophenyl 4-methoxy-2,6-dimethylbenzoate 
• 99730-38-8 4,4'-Dimethoxy-2,6,2',6'-tetramethyl-benzil 

Relevant articles and documents

Iron-Catalyzed Ortho C-H Methylation of Aromatics Bearing a Simple Carbonyl Group with Methylaluminum and Tridentate Phosphine Ligand

Iron-catalyzed C-H functionalization of aromatics has attracted widespread attention from chemists in recent years, while the requirement of an elaborate directing group on the substrate has so far hampered the use of simple aromatic carbonyl compounds such as benzoic acid and ketones, much reducing its synthetic utility. We describe here a combination of a mildly reactive methylaluminum reagent and a new tridentate phosphine ligand for metal catalysis, 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline (Me2N-TP), that allows us to convert an ortho C-H bond to a C-CH3 bond in aromatics and heteroaromatics bearing simple carbonyl groups under mild oxidative conditions. The reaction is powerful enough to methylate all four ortho C-H bonds in benzophenone. The reaction tolerates a variety of functional groups, such as boronic ester, halide, sulfide, heterocycles, and enolizable ketones.

Steric and Electronic Control of the Dissociative Hydrolysis of 4-Hydoxybenzoate Esters

The introduction of two ortho methyl substituents changes the propensity of 4-hydroxybenzoates to react via the oxo-ketene pathway by nearly one million-fold; the increased reactivity of the hindered conjugate base over that of the parent is assigned to enhanced internal nucleophilicity of the 4-oxyanion.

Vinyl Cation Intermediates in Solvolytic and Electrophilic Reactions. 1. Solvolysis of α-Arylvinyl Derivatives

The solvolysis of 16 α-arylvinyl tosylates, bromides, and chlorides has been investigated in various alcohol-water mixtures and in acetic acid at several temperatures.All substrates were substituted with either 2-methyl or 2,6-dimethyl groups to accelerate the rates of reaction.The major or exclusive product isolated in most cases was the acetophenone arising from hydrolysis of the expected enol ethers or acetates during workup.The kinetics were simple first order in the vast majority of cases, with excess base added to prevent side reactions.Leaving group effects, Winstein-Grunwald m values, Schleyer Q values, and effects of solvent nucleophilicity all point to a limiting SN1 ionization generating a vinyl cation intermediate, in which there is little rear-side nucleophilic assistance by solvent.Substituent effects led to ρ values in the range -3.9 to -5.3 vs. ?+.Activation parameters are typical for an SN1 process, and ΔS% is insensitive to the presence of zero, one, or two o-methyl groups, as are the effects of solvent polarity on the rates.The results should therefore be directly comparable with other solvolytic or electrophilic reactions generating formally similar vinyl cation intermediates.