21120-65-0

Basic information

• Product Name: 4-(4-METHYLPHENOXY)BENZOIC ACID
• Synonyms: 4-(P-TOLYLOXY)BENZOIC ACID;4-(4-METHYLPHENOXY)BENZOIC ACID;4-(4-Methylphenoxy)benzoic acid 97%
• CAS NO: 21120-65-0
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• Mol File: 21120-65-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 178-182 °C
• Boiling Point: 375.3 °C at 760 mmHg
• Flash Point: 142.8 °C
• Appearance: /
• Density: 1.208 g/cm³
• Vapor Pressure: 2.68E-06mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: 4-(4-METHYLPHENOXY)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-METHYLPHENOXY)BENZOIC ACID(21120-65-0)
• EPA Substance Registry System: 4-(4-METHYLPHENOXY)BENZOIC ACID(21120-65-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 26-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 21120-65-0(Hazardous Substances Data)

Usage

General Description

4-(4-methylphenoxy)benzoic acid is a chemical compound commonly used in the production of pharmaceuticals, agrochemicals, and chemical intermediates. It is a derivative of benzoic acid and contains a methylphenoxy group attached to the benzene ring. 4-(4-METHYLPHENOXY)BENZOIC ACID has potential anti-inflammatory and analgesic properties, making it valuable in the development of drugs for treating various diseases and conditions. Additionally, it can be utilized as a building block for synthesizing other organic compounds, including dyes, polymers, and fragrances. Its molecular structure and properties make 4-(4-methylphenoxy)benzoic acid a versatile and important chemical in the field of organic chemistry and pharmaceutical research.

InChI:InChI=1/C14H12O3/c1-10-2-6-12(7-3-10)17-13-8-4-11(5-9-13)14(15)16/h2-9H,1H3,(H,15,16)

Upstream product

• 101169-11-3 ethyl 4-(p-tolyloxy)benzoate 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 1192-96-7 potassium p-cresolate 
• 94-09-7 p-aminoethylbenzoate 
• 106-44-5 p-cresol 
• 619-58-9 4-iodobenzoic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 61343-83-7 4-(4-methylphenoxy)benzaldehyde 
• 37563-42-1 4-(4'-methylphenoxy)benzonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 21120-72-9 methyl 4-(p-tolyloxy)benzoate 
• 106-49-0 p-toluidine 
• 624-31-7 4-tolyl iodide 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 107455-96-9 4-(4-bromomethyl-phenoxy)-benzoic acid 
• 2509-18-4 4-(4-formylphenoxy)benzoic acid 
• 68548-51-6 4-(4-methylphenoxy)-benzoyl chloride 
• 1374689-27-6 C₂₀H₁₆N₂O₃S 
• 1436378-61-8 N-(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]-methyl}-2-methylpropyl-4-(4-methylphenoxy)benzamide 
• 1377996-54-7 C₂₃H₃₀N₂O₂ 
• 61343-83-7 4-(4-methylphenoxy)benzaldehyde 
• 1613189-91-5 (Z)-2-(4-(p-tolyloxy)benzylidene)benzofuran-3(2H)-one 
• 1613190-08-1 (Z)-6-hydroxy-2-(4-(p-tolyloxy)benzylidene)benzofuran-3(2H)-one 
• 1442120-35-5 4-methyl-2-({1-[4-(4-methylphenoxy)benzoyl]piperidin-4-yl}methyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-5-carboxamide 

Relevant articles and documents

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

Probing the aurone scaffold against Plasmodium falciparum: Design, synthesis and antimalarial activity

A library comprising 44 diversely substituted aurones derivatives was synthesized by straightforward aldol condensation reactions of benzofuranones and the appropriately substituted benzaldehydes. Microwave enhanced synthesis using palladium catalyzed protocols was introduced as a powerful strategy for extending the chemical space around the aurone scaffold. Additionally, Mannich-base derivatives, containing a 7-aminomethyl-6-hydroxy substitution pattern at ring A, were also prepared. Screening against the chloroquine resistant Plasmodium falciparum W2 strain identified novel aurones with IC 50 values in the low micromolar range. The most potent compounds contained a basic moiety, with the ability to accumulate in acidic digestive vacuole of the malaria parasite. However, none of those aurones revealed significant activity against hemozoin formation and falcipain-2, two validated targets expressed during the blood stage of P. falciparum infection and functional in digestive vacuole of the parasite. Overall, this study highlight (i) the usefulness of aurones as platforms for synthetic procedures using palladium catalyzed protocols to rapidly deliver lead compounds for further optimization and (ii) the potential of novel aurone derivatives as promising antimalarial compounds.