74-11-3 Usage
Chemical Properties
white to light yellow crystal powder. Soluble in methanol, anhydrous ethanol and ether, very slightly soluble in water, toluene and 95% ethanol.
Uses
Different sources of media describe the Uses of 74-11-3 differently. You can refer to the following data:
1. 4-Chlorobenzoic acid is a benzoic acid analogue that showed antifungal activity against strains of Aspergillus flavus, Aspergillus fumigatus and Aspergillus terreus, causative agents of human aspergillosis, in in vitro bioas says. It is used as a preservative.P-chlorobenzoic acid is the intermediate of fungicide dimethomorph, rodenticide Warfarin, Coumatetralyl and insecticide flumethrin, and also the intermediate of dye and medicine.
2. 4-Chlorobenzoic acid can be used:As a ligand to synthesize luminescent lanthanide complexes for bio-labeling or fiber communication applications.To prepare organotin(IV) chlorobenzoates exhibiting anticorrosion properties.As a ligand to synthesize di-n-butyl(4-chlorobenzoxy)(4-chlorobenzohydroxamato)tin(IV).
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.
Definition
ChEBI: 4-chlorobenzoic acid is a monochlorobenzoic acid carrying a chloro substituent at position 4. It has a role as a bacterial xenobiotic metabolite. It derives from a benzoic acid. It is a conjugate acid of a 4-chlorobenzoate.
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
General Description
Triclinic crystals or light fluffy white powder.4-Chlorobenzoic acid is a degradation product of indomethacin. It is degraded by Acinetobacter sp. strain ST-1 and causes its dehalogenation to yield 4-hydroxybenzoic acid under both aerobic and anaerobic conditions.
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).