4-Chlorobenzoic acid

Base Information

• Chemical Name: 4-Chlorobenzoic acid
• CAS No.: 74-11-3
• Molecular Formula: C7H5ClO2
• Molecular Weight: 156.569
• Hs Code.: 2916.39
• European Community (EC) Number: 200-805-9,695-032-0
• ICSC Number: 0503
• NSC Number: 32738,8444
• UNII: IC7888DF4L
• DSSTox Substance ID: DTXSID9024772
• Nikkaji Number: J5.259K
• Wikipedia: 4-Chlorobenzoic_acid
• Wikidata: Q2235989
• Metabolomics Workbench ID: 52012
• ChEMBL ID: CHEMBL618
• Mol file: 74-11-3.mol

Synonyms:4-chlorobenzoate;4-chlorobenzoic acid;4-chlorobenzoic acid, calcium(2:1) salt;4-chlorobenzoic acid, mercury(+1) salt;4-chlorobenzoic acid, mercury(+2)(2:1) salt;4-chlorobenzoic acid, sodium salt;4-chlorobenzoic acid, sodium salt, 11C-labeled;para-chlorobenzoic acid

Chemical Property of 4-Chlorobenzoic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline flakes
• Vapor Pressure: 0.00117mmHg at 25°C
• Melting Point: 238-241 °C
• Refractive Index: 1.5812 (estimate)
• Boiling Point: 287.2 °C at 760 mmHg
• PKA: 3.98(at 25℃)
• Flash Point: 127.5 °C
• PSA: 37.30000
• Density: 1.374 g/cm³
• LogP: 2.03820
• Storage Temp.: room temp
• Solubility.: methanol: soluble1%, clear, colorless to faintly yellow
• Water Solubility.: soluble in hot water
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 155.9978071
• Heavy Atom Count: 10
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorobenzoic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC(=CC=C1C(=O)O)Cl
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached when dispersed.
• Uses: 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. 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).

Technology Process of 4-Chlorobenzoic acid

There total 656 articles about 4-Chlorobenzoic 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: 66.6%

para-dichlorobenzene (106-46-7,84348-21-0) + carbon monoxide (201230-82-2) → terephthalic acid (100-21-0) + para-chlorobenzoic acid (74-11-3)

Guidance literature:

With sodium hydroxide; cobalt(II) acetate; In ethanol; at 30 ℃; for 20h; under 1520 Torr; Irradiation;

DOI:10.1246/cl.1987.577

Reference yield: 64.0%

N1-(p-chlorobenzoyl)-N1-(p-methylbenzyl)-N2-(p-nitrophenyl)-formamidine (130117-94-1) → N-(p-Chlorobenzoyl)-p-methylbenzylamine (41882-23-9) + N1-(p-methylbenzyl)-N2-(p-nitrophenyl)formamidine (128915-10-6) + 4-nitro-aniline (100-01-6,104810-17-5) + para-chlorobenzoic acid (74-11-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 3h; Product distribution; Ambient temperature; other N¹-acyl-N¹-alkyl-N²-(p-nitrophenyl)formamidines;

DOI:10.1248/cpb.38.1824

Reference yield: 63.0%

bromochlorobenzene (106-39-8) + carbon dioxide (124-38-9,18923-20-1) → terephthalic acid (100-21-0) + para-chlorobenzoic acid (74-11-3)

Guidance literature:

carbon dioxide; With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate; In 1,4-dioxane; at 65 ℃; for 0.333333h; Schlenk technique;

bromochlorobenzene; With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; toluene; at 100 ℃; for 16h; Schlenk technique; Sealed tube;

DOI:10.1039/c8cc06820h

upstream raw materials:

4-Cyanochlorobenzene

bromochlorobenzene

n-butyllithium

4-chloro(ethylbenzene)

Downstream raw materials:

4-chlorobenzoic anhydride

benzyl p-chlorobenzoate

benzoic-p-chlorobenzoic anhydride

(4'-chlorobenzyl) 4-chlorobenzoate

Refernces

• 1、 Stubbs,Senseman. "-". . p. 559. Retrieved 1936.
• 2、 Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui. "Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading". . . Retrieved 2021/12/13.
• 3、 Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun. "Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process". supporting information. p. 2020 - 2024. Retrieved 2022/03/31.