Benzoic Acid

Base Information

• Chemical Name: Benzoic Acid
• CAS No.: 65-85-0
• Deprecated CAS: 8013-63-6,331473-08-6,2244876-11-5
• Molecular Formula: C7H6O2
• Molecular Weight: 122.123
• Hs Code.: 2916.31
• European Community (EC) Number: 200-618-2
• ICSC Number: 0103
• NSC Number: 758203,149
• UN Number: 3077
• UNII: 8SKN0B0MIM
• DSSTox Substance ID: DTXSID6020143
• Nikkaji Number: J2.358B
• Wikipedia: Benzoic acid
• Wikidata: Q191700
• NCI Thesaurus Code: C61646
• RXCUI: 18989
• Pharos Ligand ID: K4JGK686JLC1
• Metabolomics Workbench ID: 37901
• ChEMBL ID: CHEMBL541
• Mol file: 65-85-0.mol

Synonyms:Acid, Benzoic;Benzoate, Potassium;Benzoic Acid;Potassium Benzoate;Ucephan

Chemical Property of Benzoic Acid

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 10 mm Hg ( 132 °C)
• Melting Point: 121-125 °C(lit.)
• Refractive Index: 1.504
• Boiling Point: 249.3 °C at 760 mmHg
• PKA: 4.19(at 25℃)
• Flash Point: 111.4 °C
• PSA: 37.30000
• Density: 1.197 g/cm³
• LogP: 1.38480
• Storage Temp.: Store at RT.
• Solubility.: soluble, clear, colorless (95% ethanol, 1gm/3mL)
• Water Solubility.: Slightly soluble. 0.34 g/100 mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.036779430
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

99.5% ^*data from raw suppliers

Benzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22-36-42/43-36/37/38-40-63-43-23/24/25-45-41-37/38-20/21/22-48/23-38-67-37
• Safety Statements: 26-45-37/39-24-22-36/37-24/25-23-53-36-63-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC=C(C=C1)C(=O)O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. Exposure could cause a non-allergic rash on contact.
• Chemical Properties and Uses: Benzoic acid is a white crystalline solid, slightly soluble in water. It is utilized in various industries, including chemical synthesis to produce other chemicals, as a food preservative, and for other applications. It occurs naturally in many plants and was isolated in the sixteenth century, although commercial production didn't commence until the late nineteenth century.
• Antimicrobial Properties: Benzoic acid exhibits potent antifungal properties and is effective against fungi, yeasts, and bacteria, particularly in acidic environments. Proposed mechanisms of action include changes in cell membranes, reduction of intracellular pH, and inhibition of specific enzymes. Microorganisms may acquire resistance to benzoic acid depending on various factors, including the organism and environmental conditions.
• Metabolism and Health Effects: Microorganisms can metabolize benzoic acid both aerobically and anaerobically. It is not accumulated in humans and may help reduce urinary tract infections. However, allergic reactions such as asthma and skin rashes can occur in sensitive individuals.
• Applications in Food Systems: Benzoic acid and its sodium salt, sodium benzoate, are widely used as preservatives in food systems globally. Recent applications include addition to processed meat products, incorporation into polymer coatings, and use in "active" packaging for foods. It has also been considered as a substitute for antibiotics in livestock feeds.
• Chemical Reactions and Synthesis: Decarboxylative etherification of benzoic acids with activating ortho-substituents has been achieved using specific catalyst combinations, yielding synthetically useful aryl radicals. Radical decarboxylation of benzoic acids has been explored for various reactions, including radical addition reactions and carbon metallation. However, benzoic acids are unstable during thermal processing, limiting their application in the food industry.

Technology Process of Benzoic Acid

There total 7284 articles about Benzoic 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: 40.0%

perbenzoyl p-nitrophenyl carbonate (42464-09-5) + methoxybenzene (100-66-3) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-methoxyphenyl benzoate (1523-19-9) + 2-methoxyphenyl benzoate (531-37-3) + 4-methoxy-phenol (150-76-5) + 2-methoxy-phenol (90-05-1) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 60h; Product distribution; Mechanism; influence of temperature, reagent;

DOI:10.1021/ja00405a043

Reference yield: 17.0%

3,4-bis(4-methoxyphenyl)-2,5-diphenyl-2,4-cyclopentadien-1-one (668-29-1) → 2-hydroxy-2,4-diphenyl-5-(p-methoxyphenyl)furan-3-one (72908-55-5) + 4,5-bis(4-methoxyphenyl)-3,6-diphenyl-α-pyrone (87411-92-5) + 4-methoxybenzoic acid (100-09-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With perhydrodibenzo-18-crown-6; potassium oxide; In benzene; for 120h; Ambient temperature;

DOI:10.1021/jo00172a046

Reference yield: 14.0%

toluene (108-88-3,15644-74-3,16713-13-6) → benzyl bromide (100-39-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylhydroperoxide; copper(ll) bromide; In acetic anhydride; at 80 ℃;

upstream raw materials:

2,2-dibromoacetophenone

ethyl acetate

indole

benzaldehyde

Downstream raw materials:

1,2-ethanediol, dibenzoate

4-chlorobutyl benzoate

N-(1-hydroxybutan-2-yl)benzamide

N-benzoylpiperidine

Refernces

• 1、 Agarwal, Sarswati,Chowdhury, Kakuli,Banerji, Kalyan K.. "Kinetics and Mechanism of the Oxidation of Aromatic Aldehydes by Pyridinium Fluorochromate". . p. 5111 - 5113. Retrieved 1991.
• 2、 O'Brien,Niemann. "-". . p. 1386,1388. Retrieved 1957.
• 3、 Chalfont et al.. "-". . p. 367. Retrieved 1967.
• 4、 James,Weissberger. "". . p. 2040. Retrieved 1937.
• 5、 Jaeger, David A.,Frey, Moira R.. "Preparation and Characterization of Destructible Surfactants". . p. 311 - 315. Retrieved 1982.
• 6、 Kabalka,Narayana,Reddy. "Boron triiodide-N-N-diethylaniline complex: A new reagent for cleaving esters". . p. 1793 - 1798. Retrieved 1992.
• 7、 Yamaguchi. "On cyanopigment synthesis. 3. Constitution of pigment by condensation of N, N-dimethylthiopropionamide-S-phenacylbromid with salicyladehyde". . p. 997 - 1002. Retrieved 1968.
• 8、 Menger et al.. "-". . p. 3803. Retrieved 1975.
• 9、 Briner,Demolis,Paillard. "-". . . Retrieved 1932.
• 10、 Hey et al.. "-". . p. 1477. Retrieved 1967.