54393-89-4

Basic information

• Product Name: 2-Nitro-4-(propylthio)aniline
• Synonyms: 2-nitro-4-(propylthio)aniline;2-Nitro-4-(propylthio)benzenamine;2-nitro-4-propylsulfanylaniline
• CAS NO: 54393-89-4
• Molecular Formula: C₉H₁₂N₂O₂S
• Molecular Weight: 212.27
• EINECS: 259-142-9
• Product Categories: API intermediates
• Mol File: 54393-89-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 42-43 °C
• Boiling Point: 363.5 ºC
• Flash Point: 173.6 ºC
• Appearance: light yellow solid powder
• Density: 1.25 g/cm³
• Vapor Pressure: 1.79E-05mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -0.54±0.40(Predicted)
• CAS DataBase Reference: 2-Nitro-4-(propylthio)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-4-(propylthio)aniline(54393-89-4)
• EPA Substance Registry System: 2-Nitro-4-(propylthio)aniline(54393-89-4)

Safety Data

• Hazardous Substances Data: 54393-89-4(Hazardous Substances Data)

Usage

Uses

2-Nitro-4-(propylthio)aniline is a metabolite of Albendazole (A511610), which is an anthelmintic medicine.

InChI:InChI=1/C9H12N2O2S/c1-2-5-14-7-3-4-8(10)9(6-7)11(12)13/h3-4,6H,2,5,10H2,1H3

Upstream product

• 88-74-4 2-nitro-aniline 
• 540-54-5 1-Chloropropane 
• 80825-28-1 bis(4-amino-3-nitrophenyl) disulfide 
• 187737-37-7 propene 
• 80983-47-7 4-amino-3-nitrobenzenethiol 
• 54029-45-7 2-nitro-4-thiocyanoaniline 
• 71-23-8 propan-1-ol 
• 106-94-5 propyl bromide 
• 1912-31-8 propyl methanesulfonate 

Downstream Products

• 66608-52-4 4-(propylthio)-1,2-phenylenediamine 
• 54029-48-0 1-amino-2-nitro-4-n-propylsulfinylbenzene 
• 54965-21-8 Albendazole 
• 66868-66-4 4-(1-propylsulfinyl)-1,2-diaminobenzene 
• 54029-12-8 ricobendazole 

Relevant articles and documents

Preparation method of 4-propythio-2-nitroaniline

The invention discloses a preparation method of 4-propythio-2-nitroaniline, and solves the technical problems of unreasonable preparation method, high raw material price, high toxicity, complex operation, high cost, large production of three wastes, low yield and unsuitability for industrial production in the prior art. The preparation method of 4-propythio-2-nitroaniline provided by the inventiontakes o-nitroaniline, disulfur dichloride and chloropropane as the raw materials, and carries out condensation reaction and alkylation reaction in order under the action of a catalyst so as to obtain4-propythio-2-nitroaniline. The method can be widely applied technical field of synthesis of albendazole.

A preparing method of albendazole

A preparing method of albendazole is disclosed. The method adopts 2-nitro-4-thiocyanatoaniline as a raw material, and includes salifying with an aqueous sodium hydroxide solution in an n-propanol solvent under nitrogen protection, reacting with bromopropane, and separating to obtain an n-propanol solution of 2-nitro-4-(propylthio)aniline, and therefore a problem that an impurity that is methyl 5-(methylthio)benzoimidazol-2-yl carbamate in products is high in content because steps of salifying in methanol with sodium sulfide and then reacting with bromopropane in processes at present is overcome. A technique of reducing the 2-nitro-4-(propylthio)aniline by utilizing hydrazine hydrate is adopted to replace a technique of reducing with sodium sulfide at present, thus overcoming a problem that sulfur-containing waste water is high in amount and difficult to treat in the sodium sulfide reduction technique. A methanol solution of methyl O-methyl isourea formate is adopted as a ring closing agent, thus overcoming a problem that waste water is high in amount in processes at present when cyanamide and an aqueous methyl formate solution are adopted as ring closing agents. The method is advantaged by a small waste water amount, capability of being environmental friendly, high product purity, and the like.

A PROCESS FOR PREPARATION OF ALBENDAZOLE

The present invention discloses a novel, cost-effective process for preparation of a benzimidazole carbamates compound. Specifically, it relates to the process for the preparation of anti-parasite bulk drug albendazole. The process comprises a) thiocyanating 2-nitroaniline of formula VI with ammonium thiocyanated in presence of a halogen to obtain 2-nitro-4-thiocyanoaniline of formula V; b)propylating 2-nitro-4-thiocyanoaniline of formula V with propylbromide in presence of n-propanol and a base in absence of a phase transfer catalyst to obtain 4-propylthio-2-nitroaniline of formula III; C) reducing the nitro group of 4- propylthio-2-nitroaniline prepared in step b) by reacting an aqueous alkali metal sulphide or an alkaline metal sulphide to obtain 4-propylthio-o-phenylenediamine of formula II; and d)condensing 4-propylthio-o-phenylenediamine of formula II with alkali or alkaline earth metal salt of methylcyano carbamate in presence of an acid to form Albendazole of formula I.