99-04-7 Usage
Description
m-toluic acid (MTA) , also known as 3-Methylbenzoic acid or m-Toluate, is a benzoic acid derivative having a floral honey odour. Benzoic acids are organic Compounds containing a benzene ring which bears at least one carboxyl group. Benzoic acid occurs naturally in many plants and its name was also derived from a plant source i.e. Gum benzoin. Although it is used as precursor to plasticizers, preservatives such as sodium benzoate, it also has wide application in many pharmaceutical preparations meant for treatment of fungal skin diseases, topical antiseptics, expectorants, analgesics and decongestants. The benzoic acid derivatives are also very useful due to their bacteriostatic and fragrant properties.
MTA is used as intermediate in various chemical reactions, MTA is used as a chemical intermediate in manufacturing of insect repellent and plastic stabilizer in the chemical industry. It is also used in the production of various chemicals like 3-carboxybenzaldehyde, 3-benzoylphenylacetic acid, 3-methylbenzophenone, and N,N-diethyl- 3-methylbenzamide etc.. It is a main component of N,N-diethylm-toluamide, commonly known as DEET, which is first insect repellent that can be applied to skin or clothing and provide protection against mosquitoes and other biting insects.
Chemical Properties
White to yellowish crystals. Ionization constant 5.3 × 10?5.
Slightly soluble in water; soluble in alcohol and
ether. Combustible.
Uses
Different sources of media describe the Uses of 99-04-7 differently. You can refer to the following data:
1. m-Toluic acid is used as a reagent in the preparation of hybrid molecules containing oxadiazole and thiadiazole bearing Schiff base moiety as it has antitumor activities.
2. Organic synthesis, to form N,N-diethyl-mtoluamide,
a broad-spectrum insect repellent.
Definition
ChEBI: A methylbenzoic acid carrying a methyl substituent at position 3.
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
General Description
White to yellowish crystals or mostly yellow flaky solid (with some white flakes). Has a floral-honey odor.
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.
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Isotruxene-based porous polymers as efficient and recyclable photocatalysts for visible-light induced metal-free oxidative organic transformations
Zhang, Haowen,Zhang, Xiao,Zheng, Ying,Zhou, Cen
supporting information, p. 8878 - 8885 (2021/11/27)
Two new isotruxene-based porous polymers were prepared and demonstrated to be highly efficient, metal-free heterogeneous photocatalysts for oxidative transformations using air as the mild oxidant under visible-light irradiation. Both catalysts show excellent recyclability. In addition, the reactions can be performed in water, further indicating the greenness of this method. This journal is
