74-11-3 Usage
Description
4-Chlorobenzoic acid is a benzoic acid analogue characterized by the presence of a chlorine atom at the 4-position on the benzene ring. It exhibits antifungal activity against various strains of Aspergillus, which are causative agents of human aspergillosis. This organic compound is also known for its applications as an intermediate in the synthesis of various chemical compounds.
Uses
Used in Pharmaceutical Industry:
4-Chlorobenzoic acid is used as an intermediate for the synthesis of the fungicide dimethomorph, which is effective in controlling fungal infections in crops. It is also used in the production of the rodenticide Warfarin, which is a widely used anticoagulant pesticide for controlling rodent populations.
Used in Chemical Industry:
4-Chlorobenzoic acid serves as an intermediate in the synthesis of Coumatetralyl, an intermediate for the production of pharmaceuticals and agrochemicals. Additionally, it is used in the production of the insecticide flumethrin, which is effective against various insect pests.
Used in Dye and Medicine Synthesis:
4-Chlorobenzoic acid is utilized as an intermediate in the synthesis of dyes and medicines, contributing to the development of a wide range of products in these industries.
Used in Corrosion Inhibition:
4-Chlorobenzoic acid can be used to prepare organotin(IV) chlorobenzoates, which exhibit anticorrosion properties. These compounds are useful in protecting metal surfaces from corrosion, particularly in industrial applications.
Used in Luminescent Lanthanide Complexes:
As a ligand, 4-chlorobenzoic acid is used to synthesize luminescent lanthanide complexes. These complexes have potential applications in bio-labeling and fiber communication, where their unique optical properties can be harnessed for various technological advancements.
Used in Organotin Complexes:
4-Chlorobenzoic acid is also used as a ligand to synthesize di-n-butyl(4-chlorobenzoxy)(4-chlorobenzohydroxamato)tin(IV), an organotin complex with potential applications in various fields, such as catalysis and material science.
Used as a Preservative:
Due to its antifungal properties, 4-chlorobenzoic acid is used as a preservative in various products to prevent the growth of fungi and extend their shelf life.
Preparation
4-Chlorobenzoic acid is obtained by oxidation of p-chlorotoluene: add potassium permanganate solution to the mixture of p-chlorotoluene and water in stages. The reaction is refluxed under stirring for 5-6h, then acidified with hydrochloric acid to pH 2, filtered to obtain the crude product, and recrystallized with ethanol to obtain the finished product.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 2, p. 135, 1943Synthetic Communications, 25, p. 3695, 1995 DOI: 10.1080/00397919508015507Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7
Air & Water Reactions
Insoluble in water.
Reactivity Profile
4-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.
Fire Hazard
Flash point data for 4-Chlorobenzoic acid are not available; however, 4-Chlorobenzoic acid is probably combustible.
Purification Methods
Purify it as for m-chlorobenzoic acid. It has also been crystallised from hot water, and from EtOH. [Beilstein 9 IV 973.]
Check Digit Verification of cas no
The CAS Registry Mumber 74-11-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 4 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 74-11:
(4*7)+(3*4)+(2*1)+(1*1)=43
43 % 10 = 3
So 74-11-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)/p-1
74-11-3Relevant articles and documents
A novel immobilised cobalt(III) oxidation catalyst
Das, Birinchi K.,Clark, James H.
, p. 605 - 606 (2000)
A complex form of cobalt(III) has been successfully immobilised on a chemically modified silica and proven to be an active catalyst for the selective oxidation of alkylaromatics using air as the source of oxygen and in the absence of solvent.
EVIDENCE D'UN MECANISME DE CATALYSE PAR TRANSFERT MONOELECTRONIQUE (ETC) POUR LA REACTION DE CANNIZZARO, EN PHASE HETEROGENE, EN CONDITIONS SONOCHIMIQUES
Fuentes, A.,Marinas, J.M.,Sinisterra, J.V.
, p. 2947 - 2950 (1987)
Additional evidence about an Electron Transfer Catalysis Mechanism (ETC) in the Cannizzaro reaction, catalyzed by solid bases under sonochemical conditions is shown.The reducing sites of basic solids and the ultrasound act in the first step of the ETC mechanism.
Stepwise benzylic oxygenation via uranyl-photocatalysis
Hu, Deqing,Jiang, Xuefeng
supporting information, p. 124 - 129 (2022/01/19)
Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.
Hydrolysis of amides to carboxylic acids catalyzed by Nb2O5
Siddiki,Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Jamil, Md. A. R.,Jing, Yuan,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-Ichi
, p. 1949 - 1960 (2021/03/26)
Hydrolysis of amides to carboxylic acids is an industrially important reaction but is challenging due to the difficulty of cleaving the resonance stabilized amidic C-N bond. Twenty-three heterogeneous and homogenous catalysts were examined in the hydrolysis of acetamide. Results showed that Nb2O5was the most effective heterogeneous catalyst with the greatest yield of acetic acid. A series of Nb2O5catalysts calcined at various temperatures were characterized and tested in the hydrolysis of acetamide to determine the effects of crystal phase and surface properties of Nb2O5on catalytic performance. The high catalytic performance observed was attributed mainly to the facile activation of the carbonyl bond by Lewis acid sites that function even in the presence of basic inhibitors (NH3and H2O). The catalytic studies showed the synthetic advantages of the present method, such as simple operation, catalyst recyclability, additive free, solvent free, and wide substrate scope (>40 examples; up to 95% isolated yield).