20559-55-1

Basic information

• Product Name: Oxibendazole
• Synonyms: METHYL 5-(PHENYLSULFINYL)-BENZIMIDAZOL-2-CARBAMATE;FENBENDAZOLE SULFOXIDE;(5-propoxy-1h-benzimidazol-2-yl)-carbamicacimethylester;5-propoxy-2-benzimidazolecarbamicacidmethylester;5-propoxy-2-benzimidazolecarbamicacimethylester;methyl5-n-propoxy-2-benzimidazolecarbamate;n-(2-(5-propoxybenzimidazolyl))methylcarbamate;n-(propoxy-5,benzimidazolyl)-2,carbamatedemethyle
• CAS NO: 20559-55-1
• Molecular Formula: C₁₂H₁₅N₃O₃
• Molecular Weight: 249.27
• EINECS: 243-877-7
• Product Categories: Active Pharmaceutical Ingredients;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 20559-55-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 230-231°C
• Boiling Point: 459oC
• Appearance: Crystalline solid
• Density: 1.301 g/cm³
• Refractive Index: 1.634
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), THF (Slightly, Heated)
• PKA: 10.60±0.10(Predicted)
• Merck: 14,6936
• CAS DataBase Reference: Oxibendazole(CAS DataBase Reference)
• NIST Chemistry Reference: Oxibendazole(20559-55-1)
• EPA Substance Registry System: Oxibendazole(20559-55-1)

Safety Data

• WGK Germany: 3
• RTECS: FD0835000
• Hazardous Substances Data: 20559-55-1(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 20559-55-1 differently. You can refer to the following data:
1. Anthelmintic
2. alcohol and narcotic antagonist
3. Anthelmintic.

Brand name

Anthelcide EQ (SmithKline Beecham Animal Health); Filaribits Plus (SmithKline Beecham Animal Health).

Biochem/physiol Actions

Anthelminthic

Veterinary Drugs and Treatments

Oxibendazole is indicated (labeled) for the removal of the following parasites in horses: large roundworms (Parascaris equorum), large strongyles (S. edentatus, S. equinus, S. vulgaris), small strongyles, threadworms, and pinworms (Oxyuris equi). Oxibendazole has also been used in cattle, sheep, and swine; see Dosage section for more information.

InChI:InChI=1/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

Upstream product

• 172362-95-7 5-n-propoxy-2H-benzimidazole-2-spirocyclohexane 
• 172362-91-3 5-Propoxy-1,3-dihydro-spiro[benzoimidazole-2,1'-cyclohexane] 
• 94526-10-0 5-chloro-2H-benzimidazole-2-spirocyclohexane 
• 420-04-2 CYANAMID 
• 56190-17-1 4-n-propoxy-o-phenylenediamine 
• 79-22-1 methyl chloroformate 

Downstream Products

• 104662-94-4 2-Methoxycarbonylamino-5-propoxy-benzoimidazole-1-carboxylic acid methyl ester 
• 104663-15-2 2-Methoxycarbonylamino-6-propoxy-benzoimidazole-1-carboxylic acid methyl ester 

Relevant articles and documents

2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity

Polysubstituted o-phenylenediamines were synthesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio- and 2-trifluoro-methylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 11-(pyridin-2-ylthio)dibenzo[a,c]phenazine were synthesized too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.

SYNTHESIS AND REACTIONS OF 2H-BENZIMIDAZOLE-2-SPIROCYCLOHEXANES : AN APPLICATION OF "UMPOLING"

The title compounds are available through condensation of an o-phenylenediamine with cyclohexanone followed by oxidation of the resulting product with manganese dioxide.In this article we review their oxidation, reduction, and rearrangement reactions along with their reactions with nitrogen, oxygen, sulphur, and other nucleophiles.As well as the parent compound the reactions of the 5-chloro-, 5,6-dichloro-, 4,6-dibromo-, 5-phenylsulphonyl- and 5-methoxy-derivative are discussed in some detail.Some applications of the methodology developed, particularly to the synthesis of actual or potential benzimidazole anthelminthics, are given also.