21436-44-2

Basic information

• Product Name: M-TOLUIC ANHYDRIDE
• Synonyms: 3-METHYLBENZENE-1-CARBOXYLIC ANHYDRIDE;M-TOLUIC ANHYDRIDE;3-METHYLBENZOIC ANHYDRIDE
• CAS NO: 21436-44-2
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Mol File: 21436-44-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 66-70℃
• Boiling Point: 357.5°C (rough estimate)
• Flash Point: 197.7 °C
• Appearance: /
• Density: 1.1565 (rough estimate)
• Vapor Pressure: 4.48E-07mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: M-TOLUIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: M-TOLUIC ANHYDRIDE(21436-44-2)
• EPA Substance Registry System: M-TOLUIC ANHYDRIDE(21436-44-2)

Safety Data

• Hazardous Substances Data: 21436-44-2(Hazardous Substances Data)

Usage

Description

M-Toluic anhydride, also known as 4-methylbenzoic anhydride, is a colorless, crystalline chemical compound with the molecular formula C9H8O3. It is widely recognized for its strong acylating properties and is commonly used as an intermediate in the production of pharmaceuticals and agrochemicals, as well as a reagent in organic synthesis and a precursor to various aromatic compounds.

Uses

Used in Pharmaceutical Industry:
M-Toluic anhydride is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications. Its acylating properties enable the formation of amide and ester linkages, which are essential in the construction of complex organic molecules.
Used in Agrochemical Industry:
In the agrochemical industry, M-Toluic anhydride serves as an intermediate in the production of various agrochemicals, including pesticides and herbicides. Its role in the synthesis of these compounds helps to improve agricultural productivity and crop protection.
Used in Organic Synthesis:
M-Toluic anhydride is utilized as a reagent in organic synthesis, where it is employed in the acylation of amines and alcohols. This process is crucial for the formation of various organic compounds, including amides, esters, and other derivatives, which have applications in different fields such as materials science, pharmaceuticals, and agrochemicals.
Used in Aromatic Compounds Synthesis:
As a precursor to the synthesis of various aromatic compounds, M-Toluic anhydride plays a significant role in the production of specialty chemicals and fine chemicals. These aromatic compounds are used in a wide range of applications, including fragrances, dyes, and other chemical intermediates.
It is important to handle M-Toluic anhydride with caution due to its hazardous nature, which poses potential health and environmental risks. Proper safety measures and handling procedures should be followed to minimize any risks associated with its use.

InChI:InChI=1/C16H14O3/c1-11-5-3-7-13(9-11)15(17)19-16(18)14-8-4-6-12(2)10-14/h3-10H,1-2H3

Upstream product

• 1711-06-4 3-Methylbenzoyl chloride 
• 587-03-1 3-methylbenzyl alcohol 
• 620-23-5 m-tolyl aldehyde 
• 201230-82-2 carbon monoxide 
• 625-95-6 3-Iodotoluene 
• 99-04-7 m-Toluic acid 
• 108-88-3 toluene 
• 78823-33-3 acetic acid-(3-methyl-benzoic acid )-anhydride 

Downstream Products

• 1246196-68-8 C₃₇H₅₀O₁₂ 
• 369-00-6 3-methylbenzoyl fluoride 
• 23099-05-0 3-methyl-N-phenylbenzamide 
• 643-65-2 3-methyl benzophenone 
• 1620054-58-1 C₁₇H₁₄O 

Relevant articles and documents

Organocatalytic Desymmetrisation of Fittig's Lactones: Deuterium as a Reporter Tag for Hidden Racemisation

Highly enantioselective desymmetrisation of Fittig's lactones with alcohols is promoted by bifunctional cinchona squaramides. The reactions were carried out with monodeuterated methanol to detect possible hidden racemisation of the stereogenic centre. Current evidence suggests that racemisation was not a relevant process for most substrates; partial erosion of enantioselectivity was only detected with ortho -substituted aryl derivates. The resultant glutaric acid derivatives possess a scaffold that is common in natural products and the compounds are also useful chiral building blocks for further synthetic endeavours.

TBHP/ n -Bu 4 PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C-O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert -butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

Synthesis, molecular docking, and pharmacological evaluation of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives as selective COX-2 inhibitors and anti-inflammatory agents

A series of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives (3am) was synthesized and evaluated for their in vitro inhibitory activity against COX-1 and COX-2. The compounds with considerable in vitro activity (IC50 50 values in the range of 0.06–0.71 μM. The in vivo anti-inflammatory activity of these six compounds (3a, 3b, 3d, 3g, 3j, and 3k) was assessed by the carrageenan-induced rat paw edema method. Compounds 3d (84.09%), 3g (79.54%), and 3a (70.45%) demonstrated significant anti-inflammatory activity compared to the standard drug ibuprofen (65.90%) and were also found to be safer than ibuprofen, by ulcerogenic studies. A docking study was done using the crystal structure of human COX-2, to understand the binding mechanism of these inhibitors to the active site of COX-2.