585-76-2 Usage
Description
3-Bromobenzoic acid is a white to light yellow crystal powder that is soluble in alcohols and ethers, but insoluble in water. It is an organic compound with the molecular formula C7H5BrO2 and is known for its use as a reagent in organic synthesis.
Uses
Used in Analytical Chemistry:
3-Bromobenzoic acid is used as a test solute for the determination of acidity constants by capillary zone electrophoresis. This application takes advantage of its chemical properties to study and analyze the behavior of various substances in different environments.
Used in Research and Development:
3-Bromobenzoic acid serves as an internal standard to study the retention mechanisms of an unmodified and a hydroxylated polystyrene-divinylbenzene polymer by solid-phase extraction. Its consistent properties make it an ideal reference point for understanding the behavior of other compounds in similar systems.
Used in Pharmaceutical Industry:
In the synthesis of N-(1,1-dimethyl-2-hydroxyethyl)-3-bromobenzamide, 3-bromobenzoic acid is used as a key intermediate. 3-Bromobenzoic acid has potential applications in the development of new pharmaceuticals, highlighting the importance of 3-bromobenzoic acid in the drug discovery process.
Used as an Organic Synthesis Reagent:
3-Bromobenzoic acid is also utilized as an organic synthesis reagent due to its chemical properties. Its versatility in reacting with various other compounds makes it a valuable component in the creation of new molecules and materials across different industries.
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.
Selective oxidation of alkenes to carbonyls under mild conditions
Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan
supporting information, p. 5549 - 5555 (2021/08/16)
Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.