Metronidazole benzoate

Base Information

• Chemical Name: Metronidazole benzoate
• CAS No.: 13182-89-3
• Molecular Formula: C13H13N3O4
• Molecular Weight: 275.264
• Hs Code.: 2933290000
• European Community (EC) Number: 236-131-7
• UNII: A355C835XC
• DSSTox Substance ID: DTXSID60157221
• Nikkaji Number: J213.728C
• Wikidata: Q12199321
• NCI Thesaurus Code: C87387
• RXCUI: 103866
• Metabolomics Workbench ID: 57508
• ChEMBL ID: CHEMBL1466172
• Mol file: 13182-89-3.mol

Synonyms:benzoylmetronidazole;benzoylmetronidazole monohydrate;Klion suspension

Chemical Property of Metronidazole benzoate

Chemical Property:

• Vapor Pressure: 2.88E-14mmHg at 25°C
• Melting Point: 100 °C
• Boiling Point: 487.7 °C at 760 mmHg
• PKA: 2.44±0.34(Predicted)
• Flash Point: 248.7 °C
• PSA: 89.94000
• Density: 1.31 g/cm³
• LogP: 2.47990
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in acetone, slightly soluble in alcohol.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 275.09060590
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

99% ^*data from raw suppliers

Benzoylmetronidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(N1CCOC(=O)C2=CC=CC=C2)[N+](=O)[O-]
• Recent ClinicalTrials: Study to Determine the Equivalence of Three Products Containing Metronidazole Benzoate.
• Uses: Benzoylmetronildazole is a new class of antiglycation agents used to treat diabetes mellitus. Benzoylmetronildazole is also a derivative of Metronidazole (M338880), an antibacterial in the treatment o f rosacea. Anti-infective

Technology Process of Metronidazole benzoate

There total 5 articles about Metronidazole benzoate 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: 97.38%

benzoyl chloride (98-88-4) + metronidazole (443-48-1) → 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate (13182-89-3)

Guidance literature:

With dmap; ammonium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; at 5 ℃; for 3h; pH=9; Reagent/catalyst; Temperature; Solvent; pH-value;

Reference yield: 63.0%

toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester (30575-42-9) + benzoic acid (65-85-0,8013-63-6) → 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate (13182-89-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 72h;

DOI:10.1016/j.bmc.2018.12.003

Reference yield: 36.0%

metronidazole (443-48-1) + benzoic acid (65-85-0,8013-63-6) → 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate (13182-89-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; acetone; for 18h; Ambient temperature;

DOI:10.1016/S0223-5234(97)89643-2

upstream raw materials:

metronidazole

benzoic acid

benzoyl chloride

toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester

Downstream raw materials:

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-chloro-4,5-difluorobenzoate

C₁₆H₁₉N₃O₄

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-methylbenzoate

C₁₆H₁₉N₃O₇

Refernces

• 1、 -. "Synthesis method of benzoyl metronidazole". Paragraph 0034-0061. . Retrieved 2020/11/25.
• 2、 Dubey, Sonal,Jain, Vinod,Precthi. "Evaluation of lipophilicity, antimicrobial activity and mutagenicity of some novel ester prodrugs of metronidazole". experimental part. p. 1571 - 1576. Retrieved 2010/04/02.