39220-98-9

Usage

General Description

Benzenemethanol, 3-chloro-a-(nitromethyl)- is a chemical compound with the molecular formula C8H8ClNO3. It is a derivative of benzyl alcohol and contains a nitromethyl group and a chlorine atom. Benzenemethanol, 3-chloro-a-(nitromethyl)- is commonly used in the synthesis of various pharmaceuticals and fine chemicals. It is also used as a building block in organic chemistry reactions. Due to the presence of the nitromethyl and chlorine groups, it is important to handle Benzenemethanol, 3-chloro-a-(nitromethyl)- with caution and follow proper safety protocols to prevent any harmful exposure.

Upstream product

• 75-52-5 nitromethane 
• 587-04-2 m-Chlorobenzaldehyde 
• 563-70-2 bromonitromethane 

Downstream Products

• 637780-49-5 2,4,6-triamino-5-[2-nitro-1-(3-chlorophenyl)ethyl]pyrimidine 
• 637780-48-4 2,6-diamino-5-[2-nitro-1-(3-chlorophenyl)ethyl]-3H-pyrimidin-4-one 
• 1336918-20-7 (R)-1-(3-chlorophenyl)-2-nitroethyl acetate 
• 66618-77-7 1-(3-chlorophenyl)-2-nitroethyl acetate 
• 1377577-63-3 3-chloro-N-tosylbenzamide 
• 14367-95-4 1-(3-chlorophenyl)-2-nitro-1-ethanone 
• 53360-89-7 2-amino-1-(3-chloro-phenyl)-ethanol 
• 468740-86-5 2-(3-chloro-phenyl)-2-triethylsilanyloxy-ethylamine 
• 468740-85-4 [1-(3-Chloro-phenyl)-2-nitro-ethoxy]-triethyl-silane 
• 3156-35-2 3-chloro-β-nitrostyrene 

Relevant academic research and scientific papers

Synthesis of DPA-triazole structures and their application as ligand for metal catalyzed organic reactions

In this work, the use of DPA-triazole (DPA = dipicolylamine) molecules as ligands for metal catalyzed organic reactions has been investigated. A small library of ligands has been prepared by a CuAAC (click reaction) between propargyl-DPA and different azi

One-Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β-Nitroalcohols

Biocatalytic asymmetrization of inexpensive and stable primary alcohols to prepare enantioenriched β-nitroalcohols is an important development in green chemistry for the production of chiral pharmaceutical intermediates. Herein, we report a one-pot, two-step cascade reaction sequence in which first benzylic alcohols were oxidized to produce corresponding benzaldehydes using horse liver alcohol dehydrogenase (HLADH). The in situ generated aldehydes were then reacted in a biphasic medium with nitromethane by Arabidopsis thaliana hydroxynitrile lyase (AtHNL) or Baliospermum montanum HNL (BmHNL) catalyzed Henry reaction to produce stereoselective β-nitroalcohols with (R) or (S) configuration, respectively. Using HLADH-AtHNL, (R)-β-nitroalcohols were obtained in up to 64% conversion, and HLADH-BmHNL, (S)-β-nitroalcohols in up to 70% conversion, while in both cases excellent stereoselectivity (up to >99% ee) was achieved. The concept was proven by functionalization of sp3 C?H bond of ten simple achiral benzylic alcohols to enantiocomplementary chiral β-nitroalcohols. (Figure presented.).

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: Synthesis of 2,4-disubstituted chromans

An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between o-hydroxycinnamaldehydes and α-nitroketones is developed. Prolinol TMS ether catalyst in combination with benzoic acid was found to be the most effective for this reaction which proceeds through an equilibrium of lactols to provide a single diastereomer of enantiopure 2,4-disubstituted chromans.

Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols

An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).

Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers

Here we describe a preliminary investigation on the ability of natural keratin to catalyze the nitroaldol (Henry) reaction between aldehydes and nitroalkanes. Both aromatic and heteroaromatic aldehydes bearing strong or moderate electron-withdrawing group

Selective synthesis of nitroalcohols in the presence of Ambersep 900 OH as heterogeneous catalyst

Abstract A green protocol has been developed for the selective synthesis of β-nitroalcohols using commercially available Ambersep 900 OH as reusable heterogeneous catalyst. The reaction between aldehyde and nitromethane was performed under solvent-free condition at room temperature within a short time (70-150 min) in the presence of 10 wt % of Ambersep 900 OH to produce corresponding nitroalcohols in high yield (72-91 %). After the reaction is over, the catalyst can be separated and reused (3 cycles) without appreciable loss in its activity.

Urea-pyridine bridged periodic mesoporous organosilica: An efficient hydrogen-bond donating heterogeneous organocatalyst for Henry reaction

Hydrogen-bond donating (HBD) organocatalysts have been employed as an important class of catalysts for the activation of small molecules. However, the use of these catalysts was restricted on account of the self-aggregation of HBD-active species. In this work, a successful approach was developed to construct novel urea-pyridine bridged periodic mesoporous organosilica (PMO) to prevent the unwanted self-recognition and aggregation of urea-based catalytic center by spatial isolation, unleashing its HBD organocatalytic activity along with cooperative effect from the pyridine unit for efficient Henry reaction. The urea-pyridine bridged PMO catalyst presents high structural stability and high catalytic recyclability.

Merging Asymmetric Henry Reaction with Organocatalytic Cascade Reaction for the Construction of a Chiral Indolizidine Alkaloid Skeleton

A sequential reaction combining the copper-catalyzed asymmetric Henry reaction with the organocatalytic Michael addition-hemiacetalization cascade reaction was developed. The C1-symmetric chiral diamine L1-copper complex was responsible for the first highly enantioselective Henry reaction, while diphenylprolinol silyl ether A acted as effective organocatalyst for the second cascade reaction between chiral β-nitro alcohol and α,β-unsaturated aldehydes. Via rational design and combination of the two independent catalytic systems, good yields and excellent enantioselectivities and diastereoselectivities were achieved for a broad substrate scope under mild reaction conditions. The synthetic utility of this sequential catalytic asymmetric cascade reaction was demonstrated as an alternative and straightforward stereoselective synthesis strategy for chiral indolizidine alkaloid and its analogues.

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction

Design aspects of metal-free nitrogen-based catalysts and their influence on the yield in the Henry reaction are disclosed. C 1-Symmetric, N,N-1,2-disposed amine-imine type catalysts were found to be most efficient. C 1-N,N-1,2-Disposed 1,2,3,4-tetrahydro-1,1′-biisoquinoline selectively and efficiently catalyzed the addition of nitromethane to α-keto esters and aldehydes giving exclusively the corresponding β-nitro alcohol adducts in excellent yields under very mild conditions. Georg Thieme Verlag Stuttgart New York.