3556-83-0

Basic information

• Product Name: METHYL 3-METHOXY-4-METHYLBENZOATE
• Synonyms: METHYL 3-METHOXY-P-TOLUATE;METHYL 3-METHOXY-4-METHYLBENZOATE;3-Methoxy-4-methyl-benzoesuremethylester;4-METHOXY-3-METHYLBENZOIC ACID METHYL ESTER;Methyl 3-methoxy-4-methylbenzoate, 98+%;Benzoic acid, 3-Methoxy-4-Methyl-, Methyl ester;3-Methoxy-4-methylbenzoic Acid Methyl Ester 3-Methoxy-p-toluic Acid Methyl Ester 4-Methyl-m-anisic Acid Methyl Ester Methyl 3-Methoxy-p-toluate Methyl 4-Methyl-m-anisate;Methyl 4-methyl-3-(methyloxy)benzoate
• CAS NO: 3556-83-0
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: -0
• Product Categories: Aromatic Esters;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;C10 to C11;Carbonyl Compounds;Esters
• Mol File: 3556-83-0.mol
• Article Data: 23

Chemical Properties

• Melting Point: 50-54 °C(lit.)
• Boiling Point: 119-120°C 1mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.075 g/cm³
• Vapor Pressure: 0.00723mmHg at 25°C
• Refractive Index: 1.5295
• BRN: 1948339
• CAS DataBase Reference: METHYL 3-METHOXY-4-METHYLBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-METHOXY-4-METHYLBENZOATE(3556-83-0)
• EPA Substance Registry System: METHYL 3-METHOXY-4-METHYLBENZOATE(3556-83-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 3556-83-0(Hazardous Substances Data)

Usage

Description

METHYL 3-METHOXY-4-METHYLBENZOATE, also known as Methyl 3-Methoxy-4-methylbenzoate, is an organic compound derived from the reaction of diazomethane with 3-methoxy-4-methylbenzoic acid in ether. It is characterized by its white, low melting solid appearance and is known for its chemical properties that make it a valuable reactant in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
METHYL 3-METHOXY-4-METHYLBENZOATE is used as a reactant for the preparation of antimalaria drugs, specifically those that consist of the 4-aminoquinoline pharmacophore of chloroquine combined with clotrimazole-based antimalarials. Its unique chemical properties contribute to the development of effective treatments against malaria, a disease that affects millions of people worldwide.

Preparation

Methyl 3-methoxy-4-methylbenzoate is synthesized by the following steps:A mixture of methyl 3-hydroxy-4-methylbenzoate 36 (25 g, 0.151 mol), ?Me2SO4 (28.3 ml, 0.386 mol), anhydrous K2CO3 (103.5 g, 0.75 mol) was ?refluxed in acetone for 2 hours. K2CO3 was filtered off, washed ?thoroughly with acetone. The filtrates were combined and concentrated, ?the residue was redissolved in EtOAc washed with water, dried ?(anhydrous Na2SO4), filtered and concentrated in vacuo to furnish a white solid (19.52 g). ?Yield : 72%.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 33, p. 1771, 1990 DOI: 10.1021/jm00168a036

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

Upstream product

• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 104901-43-1 methyl 3-bromo-4-methylbenzoate 
• 584-08-7 potassium carbonate 
• 121-44-8 triethylamine 
• 7151-68-0 3-methoxy-p-toluic acid 
• 144-55-8 sodium hydrogencarbonate 
• 75-36-5 acetyl chloride 
• 62454-72-2 4-methyl-3-sulfobenzoic acid 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 922-67-8 propynoic acid methyl ester 
• 108298-28-8 4-Methoxy-5-methyl-2H-pyran-2-on 

Downstream Products

• 4685-51-2 4-(chloromethyl)-2-methoxy-1-methylbenzene 
• 140462-31-3 (+/-)-faveline methyl ether 
• 112682-05-0 methyl 4-(mercaptomethyl)-3-methoxybenzoate 
• 112682-06-1 (5S,6R,7Z)-6-<<(4-carbomethoxy-2-methoxyphenyl)methyl>thio>-5-hydroxy-9-(4-heptylphenyl)-7-nonenoic acid methyl ester 
• 86239-02-3 ethyl 4-(bromomethyl)-3-methoxybenzoate 
• 86238-89-3 1-(4-carbethoxy-2-methoxyphenyl)-2-methylpropene 
• 86238-94-0 (E)-3-(4-carbethoxy-2-methoxyphenyl)-2-methylpropenal 
• 86238-78-0 (E)-1-(4-carboxy-2-methoxyphenyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene 
• 86238-87-1 diethyl (4-carbethoxy-2-methoxybenzyl)phosphonate 
• 86238-77-9 (E)-1-(4-carbethoxy-2-methoxyphenyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene 
• 17100-63-9 methyl 4-bromo-3-methoxybenzoate 
• 74733-24-7 4-formyl-3-methoxybenzoic acid methyl ester 
• 193290-55-0 C₁₀H₁₀Br₂O₃ 
• 70264-94-7 methyl 4-(bromomethyl)-3-methoxybenzoate 

Relevant articles and documents

Boosting Anti-Inflammatory Potency of Zafirlukast by Designed Polypharmacology

Multitarget design offers access to bioactive small molecules with potentially superior efficacy and safety. Particularly multifactorial chronic inflammatory diseases demand multiple pharmacological interventions for stable treatment. By minor structural changes, we have developed a close analogue of the cysteinyl-leukotriene receptor antagonist zafirlukast that simultaneously inhibits soluble epoxide hydrolase and activates peroxisome proliferator-activated receptor γ. The triple modulator exhibits robust anti-inflammatory activity in vivo and highlights the therapeutic potential of designed multitarget agents.

SUBSTITUTED INDOLES

Disclosed herein are substituted indole cysteinyl leukotriene receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

PROCESSES FOR PREPARING ZAFIRLUKAST

An improved process for the preparation of substantially pure zafirlukast and pharmaceutical compositions thereof.