28795-33-7

Basic information

• Product Name: 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole
• Synonyms: 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole
• CAS NO: 28795-33-7
• Molecular Formula: C₈H₁₃N₃O₂S
• Molecular Weight: 215.27272
• EINECS: 249-226-3
• Mol File: 28795-33-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 399.9°C at 760 mmHg
• Flash Point: 195.7°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.04E-06mmHg at 25°C
• Refractive Index: 1.6
• PKA: 2.61±0.34(Predicted)
• CAS DataBase Reference: 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole(28795-33-7)
• EPA Substance Registry System: 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole(28795-33-7)

Safety Data

• Hazardous Substances Data: 28795-33-7(Hazardous Substances Data)

Usage

Description

1-[2-(Ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole is an organic compound with the chemical formula C9H12N2O2S. It is a derivative of imidazole, a heterocyclic aromatic organic compound, and features a nitro group, an ethylthio group, and a methyl group attached to its structure. 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole serves as an important intermediate in the synthesis of various pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
1-[2-(Ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole is used as a key intermediate in the synthesis of tinidazole, an antiprotozoal and antibacterial drug. It is particularly effective against anaerobic bacteria, protozoa, and certain helminths. 1-[2-(ethylthio)ethyl]-2-methyl-5-nitro-1H-imidazole plays a crucial role in the preparation of tinidazole through a condensation-oxidation sequence using a molybdenum oxide/silica bifunctional catalyst, which enhances the efficiency and selectivity of the reaction.

InChI:InChI=1/C8H13N3O2S/c1-3-14-5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3

Upstream product

• 110-77-0 2-(ethylsulfanyl)ethanol 
• 696-23-1 2-methyl-5-nitro-1H-imidazole 

Downstream Products

• 13230-19-8 1-(2-ethylsulfanyl-ethyl)-2-methyl-4-nitro-1H-imidazole 
• 19387-91-8 tinidazole 

Relevant articles and documents

Preparation method of high-purity tinidazole

The invention discloses a synthetic preparation method of high-purity tinidazole, and belongs to the technical field of chemical pharmacy. The method includes: taking beta-hydroxyethyl sulfide and 2-methyl-5-nitroimidazole as the raw materials, using 4-methyl-2-pentanone as a solvent, conducting dehydration condensation under the action of concentrated sulfuric acid to obtain a condensation compound 2-methyl-1-(2-ethylthioethyl)-5-nitro-1H-imidazole, and then under the catalysis of sodium molybdate, performing oxidization to generate a tinidazole crude product; and decoloring and refining thecrude product with water to obtain a tinidazole finished product with purity of greater than or equal to 99.98%. Compared with the prior art, the raw materials are easy to obtain, reaction is simple,and operation is easy and convenient; meanwhile, the incompletely reacted 2-methyl-5-nitroimidazole and the recycled 4-methyl-2-pentanone can be directly applied mechanically, so that the production cost is effectively reduced, the reaction period is shortened, pollution is reduced, and the yield and the product quality are improved.

Regioselective Alkylation of 4(5)-Nitro-1H-Imidazoles in Acidic Media: Study of Temperature Effects

Alkylation of 4(5)-nitro-1H-imidazoles in acidic media with reactive alkylating agents such as benzyl chloride and allyl bromide resulted in the predominant formation of the 5-nitro isomers at lower temperatures (75 deg C) and the 4-nitro isomers at higher temperatures (140 deg C).With less reactive alkylating agents, only the 5-nitro isomers were produced irrespective of temperature.The mechanism was shown to involve quaternization of the initially formed 1-alkyl-5-nitro-1H-imidazoles followed by preferential dealkylation to yield the thermodynamically more stable 4-nitro-1H-imidazoles.