4-Bromobenzoic acid

Base Information

• Chemical Name: 4-Bromobenzoic acid
• CAS No.: 586-76-5
• Molecular Formula: C7H5BrO2
• Molecular Weight: 201.019
• Hs Code.: 29163900
• European Community (EC) Number: 209-581-7
• NSC Number: 17582
• UNII: 6992P6102O
• DSSTox Substance ID: DTXSID7060413
• Nikkaji Number: J43.481G
• Wikidata: Q18472729
• Metabolomics Workbench ID: 61232
• ChEMBL ID: CHEMBL22051
• Mol file: 586-76-5.mol

Synonyms:4-Bromobenzoic acid;586-76-5;P-BROMOBENZOIC ACID;Benzoic acid, 4-bromo-;p-Carboxybromobenzene;p-Bromobenzenecarboxylic acid;Benzoic acid, p-bromo-;Para Bromo Benzoic Acid;4-Bromo-benzoic acid;4-Bromobenzoicacid;MFCD00002529;4-Brom-benzoesaeure;4-carboxybromobenzene;EINECS 209-581-7;NSC 17582;BRN 1906923;4-bromobenzenecarboxylic acid;AI3-08859;CHEBI:60698;UNII-6992P6102O;NSC-17582;6992P6102O;4-09-00-01017 (Beilstein Handbook Reference);NSC-143357;NSC-176126;Z82;4-BrombenZoic acid;4Bromo-benzoic acid;4-brom-benzoic acid;4- bromobenzoic acid;4-Bromo benzoic acid;4-Bromobenzoic acid (1);4-Bromophenylcarboxylic acid;4-Bromobenzoic acid, 98%;SCHEMBL71380;BROMOBENZOIC ACID, P-;CHEMBL22051;DTXSID7060413;4-BROMOBENZOIC ACID [MI];BDBM239163;NSC17582;STR02440;STK301567;AKOS000118916;CS-W020100;PS-5301;NCGC00340397-01;BP-31040;LS-36195;SY001067;AM20050209;B0553;FT-0649860;EN300-18038;B-5782;AB00376738-03;AE-641/00396064;4-Bromobenzoic acid, Vetec(TM) reagent grade, 98%;W-105369;Q18472729;Z57127530;F2191-0080

Chemical Property of 4-Bromobenzoic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.000519mmHg at 25°C
• Melting Point: 252-254 °C(lit.)
• Refractive Index: 1.608
• Boiling Point: 299.8 °C at 760 mmHg
• PKA: 3.96(at 25℃)
• Flash Point: 135.1 °C
• PSA: 37.30000
• Density: 1.701 g/cm³
• LogP: 2.14730
• Storage Temp.: -20°C
• Solubility.: ethanol: soluble5%
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.94729
• Heavy Atom Count: 10
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

4-Bromobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-36-37/38
• Safety Statements: 26-36-24/25-22-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC(=CC=C1C(=O)O)Br
• Uses: 4-Bromobenzoic acid was used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry. It is also used as an intermediate for the synthesis of agrochemicals, pharmaceutical, chemical intermediates and liquid crystals. 4-Bromobenzoic acid was used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.

Technology Process of 4-Bromobenzoic acid

There total 373 articles about 4-Bromobenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → biphenyl-4-acetaldehyde (92-91-1) + 4-Bromobenzoic acid (586-76-5) + biphenyl-4-carboxylic acid (92-92-2)

Guidance literature:

para-bromoacetophenone; phenylboronic acid; immobilized 4-bromobenzoic acid; With potassium carbonate; In water; N,N-dimethyl-formamide;

With potassium hydroxide; In ethanol; water;

DOI:10.1016/j.poly.2019.06.057

Reference yield: 79.0%

para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → biphenyl-4-acetaldehyde (92-91-1) + 4-Bromobenzoic acid (586-76-5) + biphenyl-4-carboxylic acid (92-92-2)

Guidance literature:

para-bromoacetophenone; phenylboronic acid; With potassium carbonate; In water; N,N-dimethyl-formamide; at 90 ℃; for 12h;

With potassium hydroxide; In ethanol; water; N,N-dimethyl-formamide; at 90 ℃; for 72h;

DOI:10.1016/j.jorganchem.2013.08.042

Reference yield: 72.0%

chloroform (67-66-3,8013-54-5) + 4,4'-dibromodiphenyliodonium chloride (53601-22-2) → 1,4-bromoiodobenzene (589-87-7) + 4-Bromobenzoic acid (586-76-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; at 50 ℃; for 1h;

DOI:10.1039/a900126c

upstream raw materials:

methanol

3-(4-bromophenyl)-2-methyl-3-oxopropanenitrile

n-butyllithium

diethyl ether

Downstream raw materials:

4-methoxycarbonylphenyl bromide

Ethyl 4-bromobenzoate

1-(4-bromo-benzoylamino)-1-deoxy-D-glucitol

4-bromo-4'-methoxybenzophenone

Refernces

• 1、 Kleene. "-". . p. 2883. Retrieved 1940.
• 2、 Bortolini, Olga,Chiappe, Cinzia,Fogagnolo, Marco,Massi, Alessandro,Pomelli, Christian Silvio. "Formation, Oxidation, and Fate of the Breslow Intermediate in the N-Heterocyclic Carbene-Catalyzed Aerobic Oxidation of Aldehydes". . p. 302 - 312. Retrieved 2017.
• 3、 Rao, Gyandshwar Kumar,Kumar, Arun,Singh, Mahabir Pratap,Singh, Ajai K.. "Palladium(II) complex of an organotellurium ligand as a catalyst for Suzuki Miyaura coupling: Generation and role of nano-sized Pd3Te 2". . p. 1 - 6. Retrieved 2014.
• 4、 Barrett, Anthony G. M.,Cramp, Susan M.,Roberts, Richard S.. "ROMP-spheres: A novel high-loading polymer support using cross metathesis between vinyl polystyrene and norbornene derivatives". . p. 1083 - 1086. Retrieved 1999.
• 5、 Upadhyay, Rahul,Rana, Rohit,Sood, Aakriti,Singh, Vikash,Kumar, Rahul,Srivastava, Vimal Chandra,Maurya, Sushil K.. "Heterogeneous vanadium-catalyzed oxidative cleavage of olefins for sustainable synthesis of carboxylic acids". supporting information. p. 5430 - 5433. Retrieved 2021/06/09.
• 6、 Hassan Tolba, Amal,Krupi?ka, Martin,Chudoba, Josef,Cibulka, Radek. "Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative". supporting information. p. 6825 - 6830. Retrieved 2021/09/11.