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)
Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives
Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan
, p. 5298 - 5302 (2021/06/30)
The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.
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.