13407-16-4

Usage

Uses

Used in Pharmaceutical Industry:
Benzenemethanol, alpha-(chloromethyl)-4-nitro(9CI) is used as a key reagent in the synthesis of monocyclic nitroimidazole analogs of econazole. These analogs possess antitubercular activity, making them important for the development of new treatments against tuberculosis, a disease that continues to pose significant health challenges worldwide.
In the synthesis process, the compound serves as a building block, contributing to the formation of the desired nitroimidazole structure. Its reactivity and functional groups play a crucial role in the chemical reactions that lead to the final product, which can then be further optimized for improved efficacy and safety in treating tuberculosis.

Upstream product

• 7647-01-0 hydrogenchloride 
• 90221-54-8 2-bromo-1-(4-nitro-phenyl)-1-nitryloxy-ethane 
• 6388-74-5 p-Nitrophenyloxirane 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 
• 593-71-5 Chloroiodomethane 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 216160-44-0 (S)-2-chloro-1-(4-nitrophenyl)ethanol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 
• 1283135-50-1 2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanol 
• 1283135-25-0 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanol 
• 6388-74-5 p-Nitrophenyloxirane 
• 6388-74-5 (2R)-2-(4-nitrophenyl)oxirane 

Relevant academic research and scientific papers

Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF 3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effe

Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).

External trapping of halomethyllithium enabled by flow microreactors

This work demonstrates that the accurate control of the reaction parameters realized within microreactor systems allowed for a taming of the reactivity of thermally unstable intermediates such as haloalkyllithiums. The first example of effective external trapping of a reactive carbenoid such as the chloromethyllithium is described. By using microreactor systems, a continuous flow synthesis of chloro alcohols and chloro amines could be achieved with high yields. By controlling the residence time the highly reactive chloromethyllithium could be generated and reacted with electrophiles at temperatures much higher than in batch-mode and without internal quenching. The developed continuous-flow process matches the requirements for sustainability.

Efficient synthesis of chlorohydrins using ClCH2MgCl·LiCl

The mixed lithium-magnesium carbenoid ClCH2MgCl·LiCl was easily generated in THF through the reaction of chloroiodomethane with i-PrMgCl·LiCl at -78 °C. This reagent reacts well with a number of aldehydes to give the corresponding chlorohydrins in good yields.

Dynamic kinetic resolution of racemic β-haloalcohols: Direct access to enantioenriched epoxides

The direct chemo-enzymatic DKR of racemic β-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for β-haloalcohols. Copyright