99-04-7 Usage
Description
m-Toluic acid (MTA), also known as 3-Methylbenzoic acid or m-Toluate, is a benzoic acid derivative with a floral honey odor. Benzoic acids are organic compounds containing a benzene ring with at least one carboxyl group. MTA is used as a precursor to plasticizers and preservatives, and has wide applications in pharmaceutical preparations for treating fungal skin diseases, topical antiseptics, expectorants, analgesics, and decongestants. Its bacteriostatic and fragrant properties make it useful in various chemical reactions and industries.
Uses
Used in Pharmaceutical Industry:
m-Toluic acid is used as a precursor for the synthesis of pharmaceutical compounds, including treatments for fungal skin diseases, topical antiseptics, expectorants, analgesics, and decongestants.
Used in Chemical Industry:
m-Toluic acid is used as a chemical intermediate in the manufacturing of insect repellents and plastic stabilizers. It is also used in the production of various chemicals such as 3-carboxybenzaldehyde, 3-benzoylphenylacetic acid, 3-methylbenzophenone, and N,N-diethyl-3-methylbenzamide.
Used in Insect Repellent Industry:
m-Toluic acid is a main component of N,N-diethylm-toluamide, commonly known as DEET, which is the first insect repellent that can be applied to skin or clothing and provide protection against mosquitoes and other biting insects.
Used in Organic Synthesis:
m-Toluic acid is used as a reagent in the preparation of hybrid molecules containing oxadiazole and thiadiazole bearing Schiff base moiety, which have antitumor activities. It is also used in the synthesis of N,N-diethyl-m-toluamide, a broad-spectrum insect repellent.
Synthesis Reference(s)
Tetrahedron, 51, p. 4991, 1995 DOI: 10.1016/0040-4020(95)98696-FTetrahedron Letters, 32, p. 5931, 1991 DOI: 10.1016/S0040-4039(00)79429-9
Reactivity Profile
m-Toluic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in m-Toluic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. m-Toluic acid is incompatible with strong oxidizers.
Fire Hazard
Flash point data for m-Toluic acid are not available; however, m-Toluic acid is probably combustible.
Flammability and Explosibility
Notclassified
Purification Methods
Crystallise the acid from water. [Beilstein 9 IV 1712.] Aromatic acid impurities (to <0.05%) can be removed via the (±)--methylbenzylamine salt as described for 2,4-dichlorobenzoic acid [Ley & Yates Organic Process Research & Development 12 120 2008]. The S-benzylisothiuronium salt has m 140o (from aqueous EtOH).
Check Digit Verification of cas no
The CAS Registry Mumber 99-04-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 99-04:
(4*9)+(3*9)+(2*0)+(1*4)=67
67 % 10 = 7
So 99-04-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)/p-1
99-04-7Relevant articles and documents
On the possible causes of enhancement of the heterogeneous catalytic liquid-phase oxidation reaction of m-xylene by microwave radiation
Litvishkov,Tret'Yakov,Talyshinskii,Shakunova,Zul'Fugarova,Mardanova,Nagdalieva
, p. 117 - 120 (2013)
The contribution of the heterogeneous component of the total conversion of m-xylene to the process of its heterogeneous catalytic liquid-phase oxidation has been studied, as this contribution is most clearly manifested in the case of microwave treatment. It has been shown that microwave irradiation shortens the induction period of the reaction taken to reach a steady state. It has been suggested that the observed increase in the generation rate of free m-xylyl radicals by microwave treatment is due to the appearance at the hydrocarbons/catalyst interface of local overheating regions whose temperature can exceed the weight-average temperature in the reaction space.
Efficiency of lithium cations in hydrolysis reactions of esters in aqueous tetrahydrofuran
Hayashi, Kazuhiko,Ichimaru, Yoshimi,Sugiura, Kirara,Maeda, Azusa,Harada, Yumi,Kojima, Yuki,Nakayama, Kanae,Imai, Masanori
, p. 581 - 594 (2021/06/06)
Lithium cations were observed to accelerate the hydrolysis of esters with hydroxides (KOH, NaOH, LiOH) in a water/tetrahydrofuran (THF) two-phase system. Yields in the hydrolysis of substituted benzoates and aliphatic esters using the various hydroxides were compared, and the effects of the addition of lithium salt were examined. Moreover, it was presumed that a certain amount of LiOH was dissolved in THF by the coordination of THF with lithium cation and hydrolyzed esters even in the THF layer, as in the reaction by a phase-transfer catalyst.
Bimetallic oxide nanoparticles confined in ZIF-67-derived carbon for highly selective oxidation of saturated C–H bond in alkyl arenes
Huang, Cheng,Su, Xiaoyan,Gu, Xiangyu,Liu, Rui,Zhu, Hongjun
, (2020/10/15)
Zeolite imidazolate frameworks (ZIFs) have recently emerged as an ideal type of carbon precursors with abundant tailorability. In this work, a series of ZIF-derived porous carbon catalysts have been prepared with encapsulation of bimetallic oxide nanoparticles via simple thermal treatment. The composition and structure of these catalysts were confirmed in detail by different characterization methods. The bimetallic oxide (Mn/Co, Fe/Co, and Cu/Co) nanoparticles were encapsulated in the nitrogen-doped graphitized carbon matrix. Moreover, the hierarchically porous structure and carbon defects were successfully constructed in the carbon catalysts. Additionally, in the selective oxidation of saturated C–H bonds in alkyl arenes, the carbon catalysts demonstrate outstanding performance for the oxidation of C–H bonds to corresponding carboxyl groups. This was due to their unique structure can greatly promote mass transfer and molecular oxygen activation, resulting in high conversion and high selectivity. Remarkably, this work here could also provide a novel strategy to the controllable synthesis of metal–organic frameworks (MOFs)-derived carbon catalysts for enhanced performance in heterogeneous catalysis.