585-76-2 Usage
Chemical Properties
white to light yellow crystal powder. soluble in alcohols and ethers, insoluble in water.Used as organic synthesis reagent.
Uses
3-Bromobenzoic acid was used as test solute in the determination of acidity constants by capillary zone electrophoresis. It was used as internal standard to study the retention mechanisms of an unmodified and a hydroxylated polystyrene-divinylbenzene polymer by solid-phase extraction. It was also used in synthesis of N-(1,1-dimethyl-2-hydroxyethyl)-3-bromobenzamide.
Preparation
3-Bromobenzoic acid is synthesized from 3-bromotoluene by oxidation of potassium permanganate. Mix m-bromotoluene, potassium hydroxide and water, heat to boiling, slowly add potassium permanganate, and reflux for 4 hours after adding. After acidification by filtration, the crude product was obtained by filtration. Then it is dissolved in ethanol with ammonia water, acidified with hydrochloric acid, filtered and washed with water to obtain 3-bromobenzoic acid.
Synthesis Reference(s)
The Journal of Organic Chemistry, 15, p. 481, 1950 DOI: 10.1021/jo01149a007
Purification Methods
Crystallise the acid from acetone/water, MeOH or acetic acid. The anilide has m 137o (from EtOH/H2O). [Beilstein 9 IV 1013.]
Check Digit Verification of cas no
The CAS Registry Mumber 585-76-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 5 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 585-76:
(5*5)+(4*8)+(3*5)+(2*7)+(1*6)=92
92 % 10 = 2
So 585-76-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H5BrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)/p-1
585-76-2Relevant articles and documents
Harris,Smith
, p. 168 (1936)
Aerobic oxidation of aldehydes to carboxylic acids catalyzed by recyclable ag/c3 n4 catalyst
Wu, Chaolong,Yao, Xiaoquan,Yu, Min,Zhou, Li,Zhu, Li
, p. 167 - 175 (2021/03/19)
The oxidation of aldehydes is an efficient methodology for the synthesis of carboxylic acids. Herein we hope to report a simple, efficient and recyclable protocol for aerobic oxidation of aldehydes to carboxylic acid by using C3N4 supported silver nanoparticles (Ag/C3N4) as a catalyst in aqueous solution under mild conditions. Under standard conditions, the corresponding carboxylic acids can be obtained in good to excellent yields. In addition, Ag/C3N4 is convenient for recovery and could be reused three times with satisfactory yields.
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.