76116-24-0

Basic information

• Product Name: (R)-(1-(3-nitrophenyl))ethanol
• Synonyms: (R)-(1-(3-nitrophenyl))ethanol;(R)-1-(3-nitrophenyl)ethanol(WXC08934)
• CAS NO: 76116-24-0
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16196
• EINECS: -0
• Mol File: 76116-24-0.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 218℃
• Flash Point: 124℃
• Appearance: /
• Density: 1.263
• Storage Temp.: 2-8°C
• PKA: 13.89±0.20(Predicted)
• CAS DataBase Reference: (R)-(1-(3-nitrophenyl))ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(1-(3-nitrophenyl))ethanol(76116-24-0)
• EPA Substance Registry System: (R)-(1-(3-nitrophenyl))ethanol(76116-24-0)

Safety Data

• Hazardous Substances Data: 76116-24-0(Hazardous Substances Data)

Usage

General Description

(R)-(1-(3-nitrophenyl))ethanol is a chiral compound with a nitrophenyl group attached to a hydroxyl group. It is commonly used in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. (R)-(1-(3-nitrophenyl))ethanol has potential applications in medicinal chemistry as a building block for the preparation of biologically active molecules. It can also be used as a chiral resolving agent in chromatographic separations. The presence of the nitro group makes this compound reactive and potentially useful in organic synthesis for the formation of carbon-carbon or carbon-heteroatom bonds. Additionally, its chiral nature makes it valuable for the production of enantiomerically pure compounds.

Upstream product

• 5400-78-2 1-(3-nitrophenyl)ethanol 
• 17279-31-1 (-)-(S)-N,N-dimethyl-1-phenylethylamine 
• 108-24-7 acetic anhydride 
• 121-89-1 3-Nitroacetophenone 
• 1369493-63-9 1-(3-nitrophenyl)ethyl acrylate 
• 75-89-8 2,2,2-trifluoroethanol 
• 188015-95-4 (S)-1-(3-nitrophenyl)ethyl tosylate 
• 544-97-8 dimethyl zinc(II) 
• 99-61-6 3-nitro-benzaldehyde 
• 108-05-4 vinyl acetate 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 72802-41-6 2-hydroxy-1-(3-nitrophenyl)ethan-1-one 
• 90945-65-6 2-acetoxy-1-(3-nitrophenyl)ethanone 
• 2227-64-7 3'-nitro-2-bromoacetophenone 

Downstream Products

• 1027256-88-7 (R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine 
• 317830-26-5 (S)-1-(1-azidoethyl)-3-nitrobenzene 
• 103966-64-9 (R)-1-(3-nitrophenyl)ethyl acetate 
• 90271-37-7 (S)-1-(3 -nitrophenyl)ethan-1-amine 
• 1610767-01-5 tert-butyl (S)-(1-(3-aminophenyl)ethyl)carbamate 

Relevant articles and documents

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h?1. Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

Asymmetric reduction of prochiral aromatic and hetero aromatic ketones using whole-cell of Lactobacillus senmaizukei biocatalyst

Asymmetric bioreduction of aromatic and heteroaromatic ketones is an important process in the production of precursors of biologically active molecules. In this study, the bioreduction of aromatic and hetero aromatic prochiral ketones into optically active alcohols was investigated using Lactobacillus senmaizukei as a whole-cell catalyst, since whole-cells are less expensive than pure enzymes. The study indicates enantioselective bioreduction of various substituted aromatic ketones (1–16) to the corresponding (R)-and (S)-chiral secondary alcohols (1a–16a) in low to excellent enantioselectivity (6–94%) with good yields (58–95%). In addition, heteroaromatic prochiral ketones 1-(pyridin-2-yl)ethanone (17) and 1-(furan-2-yl)ethanone (18) were reduced to (R)-17a and (R)-18a in enantiopure form with excellent conversion (>99%) and yields. These findings show that L. senmaizukei is a very important biocatalyst for asymmetric reduction of both 6-membered and 5-member heteroaromatic methyl ketones. This method promising a green synthesis for the synthesis of biologically important secondary chiral alcohols in an environmentally friendly and inexpensive process.

Boron containing chiral Schiff bases: Synthesis and catalytic activity in asymmetric transfer hydrogenation (ATH) of ketones

Asymmetric Transfer Hydrogenation (ATH) has been an attractive way for the reduction of ketones to chiral alcohols. A great number of novel and valuable synthetic pathways have been achived by the combination usage of organometallic and coordination chemistry for the production of important class of compounds and particularly optically active molecules. For this aim, four boron containing Schiff bases were synthesized by the reaction of 4-formylphenylboronic acid with chiral amines. The boron containing structures have been found as stable compounds due to the presence of covalent B–O bonds and thus could be handled in laboratory environment. They were characterized by 1H NMR and FT-IR spectroscopy and elemental analysis and they were used as catalyst in the transfer hydrogenation of ketones to the related alcohol derivatives with high conversions (up to 99%) and low enantioselectivities (up to 22% ee).