Benzocaine

Base Information

• Chemical Name: Benzocaine
• CAS No.: 94-09-7
• Deprecated CAS: 71123-91-6,1865741-16-7
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: Oral rat LD50: 3040 mg/kg
• European Community (EC) Number: 202-303-5
• NSC Number: 755909,41531,4688
• UNII: U3RSY48JW5
• DSSTox Substance ID: DTXSID8021804
• Nikkaji Number: J4.690F
• Wikipedia: Benzocaine
• Wikidata: Q422745
• NCI Thesaurus Code: C28923
• RXCUI: 1399
• Pharos Ligand ID: XCPNWX3CQBWX
• Metabolomics Workbench ID: 38689
• ChEMBL ID: CHEMBL278172
• Mol file: 94-09-7.mol

Synonyms:4-Aminobenzoic Acid Ethyl Ester;Acetate, Benzocaine;Americaine;Anaesthesin;Anesthesin;Bensokain;Benzocaine;Benzocaine Acetate;Benzocaine Formate;Benzocaine Hydrobromide;Benzocaine Hydrochloride;Benzocaine Methanesulfonate;Ethoform;Ethyl Aminobenzoate;Formate, Benzocaine;Hydrobromide, Benzocaine;Hydrochloride, Benzocaine;Methanesulfonate, Benzocaine

Chemical Property of Benzocaine

Chemical Property:

• Appearance/Colour: white odourless crystals
• Vapor Pressure: 0.000589mmHg at 25°C
• Melting Point: 88-90 °C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 310.7 °C at 760 mmHg
• PKA: 2.5(at 25℃)
• Flash Point: 164.2 °C
• PSA: 52.32000
• Density: 1.13 g/cm^>3
• LogP: 2.02670
• Storage Temp.: 0-6°C
• Solubility.: alcohol: soluble1 gm in 5 ml
• Water Solubility.: Soluble in ethanol, chloroform, ethyl ether and dilute acids. Sparingly soluble in water
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

Benzocaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 43-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 22-24/25-37/39-26-24-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CCOC(=O)C1=CC=C(C=C1)N
• Recent ClinicalTrials: Effectiveness of Laser Photobiomodulation Therapy in Reducing Child Pain During Local Anesthesia Injection
• Recent EU Clinical Trials: Open, Randomized, Active Comparator-controlled, Multi-Center Study to Evaluate Safety and Efficacy of IBsolvMIR? in Islet Transplantation
• Recent NIPH Clinical Trials: Analgesic effects of Emla cream as topical anesthetic for gingiva.
• Biological Potentials: Analogs of benzocaine have demonstrated various biological potentials, including antibacterial, antifungal, and anti-cancer properties.; Some derivatives show notable activity against tuberculosis.
• Chemical Reactions and Derivatives: Electrophilic and nucleophilic reactions of benzocaine are commonly employed to synthesize a library of benzocaine derivatives with diverse biological activities.
• Chemical Structure: Benzocaine, or ethyl 4-aminobenzoate, is an ester derived from 4-aminobenzoic acid. It is widely used as a topical anesthetic, antipruritic drug, allergen, and sensitizer.
• Role as an Anesthetic: Widely used in oral ulcers, ear pain, and dental complications as an anesthetic agent. Along with lidocaine and other local anesthetics, benzocaine is utilized in surgical procedures and acts as a blocker of Na+ channels.
• Clinical Efficacy: Several placebo-controlled studies support the effectiveness of benzocaine in relieving toothache.; Some products containing benzocaine are applied to both the affected tooth and surrounding soft tissue.
• Veterinary Use: Benzocaine has been confirmed as an effective anesthetic for Colossoma macropomum (tambaqui) juveniles, providing rapid immobilization and recovery. It is a cost-effective option compared to other available anesthetic compounds.
• Regulatory Considerations: The FDA has requested additional pivotal studies to determine the efficacy of benzocaine for toothache relief and to assess dose-response between different formulations.; Product labels must ensure safe dosing for the relief of toothache pain.

Technology Process of Benzocaine

There total 114 articles about Benzocaine 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: 99.0%

Ethyl 4-bromobenzoate (5798-75-4) → p-aminoethylbenzoate (94-09-7)

Guidance literature:

With copper (II)-fluoride; trimethylsilylazide; ethanolamine; In N,N-dimethyl acetamide; at 95 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.200903511

Reference yield: 99.0%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → p-aminoethylbenzoate (94-09-7)

Guidance literature:

ethyl 4-oxocyclohexane-1-carboxylate; With hydroxylamine hydrochloride; potassium carbonate; In N,N-dimethyl acetamide; at 20 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

at 130 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.7b07347

Reference yield: 95.0%

ethyl cyclohexanecarboxylate (3289-28-9) → p-aminoethylbenzoate (94-09-7)

Guidance literature:

With ethene; 5%-palladium/activated carbon; ammonium acetate; potassium carbonate; In acetonitrile; at 90 ℃; for 3h; under 760.051 Torr; Reagent/catalyst; Schlenk technique;

DOI:10.1021/acs.orglett.0c04056

upstream raw materials:

ethyl 4-nitrobenzoate

4-nitro-benzoic acid-(2,2,2-trichloro-ethyl ester)

2-(diethylamino)ethyl 2-chloro-4-nitrobenzoate

ethanol

Downstream raw materials:

ethyl 4-benzoate

ethyl 4-benzoate

4-(2-mercapto-ethylamino)-benzoic acid ethyl ester

4-amino-benzoic acid-(2-piperidino-ethyl ester)

Refernces

• 1、 Abdullaev. "Anesthesin synthesized by hydrogenation of p-nitrobenzoic acid ethyl ester on palladium catalysts". . p. 45 - 48. Retrieved 2001.
• 2、 Al'Tshuler,Shkurenko,Gorlov. "Kinetics of the reduction of p-nitrobenzoic acid esters in nanoreactors on the basis of sulfonated polymers". . p. 372 - 375. Retrieved 2015.
• 3、 Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter. "Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions". . p. 133 - 146. Retrieved 2021/11/04.
• 4、 Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua. "Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer". . p. 9561 - 9568. Retrieved 2021/08/06.