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

• 121-89-1 3-Nitroacetophenone 
• 112022-81-8 (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole 
• 67-63-0 isopropyl alcohol 
• 19759-28-5 (+/-)-1-(3-nitrophenyl)ethyl acetate 
• 5400-78-2 1-(3-nitrophenyl)ethanol 
• 287944-26-7 (S)-(+)-1-(3-nitrophenyl)-1,2-ethanediol 
• 2227-64-7 3'-nitro-2-bromoacetophenone 
• 90945-65-6 2-acetoxy-1-(3-nitrophenyl)ethanone 
• 72802-41-6 2-hydroxy-1-(3-nitrophenyl)ethan-1-one 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 108-05-4 vinyl acetate 
• 544-97-8 dimethyl zinc(II) 
• 99-61-6 3-nitro-benzaldehyde 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

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

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.

Arene-Immobilized Ru(II)/TsDPEN Complexes: Synthesis and Applications to the Asymmetric Transfer Hydrogenation of Ketones

The Noyori-Ikariya (arene)Ru(II)/TsDPEN precatalyst has been anchored to amorphous silica and DAVISIL through the η6-coordinated arene ligand via a straightforward synthesis and the derived systems, (arene)Ru(II)/TsDPEN@silica and (arene)Ru(II)/TsDPEN@DAVISIL, form highly efficient catalysts for the asymmetric transfer hydrogenation of a range of electron-rich and electron-poor aromatic ketones, giving good conversion and excellent ee's under mild reaction conditions. Moreover, catalyst generated in situ immediately prior to addition of substrate and hydrogen donor, by reaction of silica-supported [(arene)RuCl2]2 with (S,S)-TsDPEN, was as efficient as that generated from its preformed counterpart [(arene)Ru{(S,S)-TsDPEN}Cl]@silica. Gratifyingly, the initial TOFs (up to 1085 h?1) and ee's (96–97 %) obtained with these catalysts either rivalled or outperformed those previously reported for catalysts supported by either silica or polymer immobilized through one of the nitrogen atoms of TsDPEN. While the high ee's were also maintained during recycle studies, the conversion dropped steadily over the first three runs due to gradual leaching of the ruthenium.

One-pot kinetic resolution-Mitsunobu reaction to access optically pure compounds, using silver salts in the substitution protocol

A practical method is developed to access chiral arylalkyl carbinols with a high yield from racemic alcohols. A one-pot enzyme mediated Kinetic Resolution followed by Mitsunobu esterification of the unreacted enantiomer of alcohol with metal acetate results in a nearly complete formation of chiral acetate. Substitution with AgOAc was found to be the most efficient, and the use of sub stoichiometric amounts of AgNO3 and excess of NaOAc affords comparable results; the protocol was further extended to introduce azide as a nucleophile.