1335017-70-3

Basic information

• Product Name: (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol
• Synonyms: (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol
• CAS NO: 1335017-70-3
• Molecular Weight: 227.217
• Mol File: 1335017-70-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol(1335017-70-3)
• EPA Substance Registry System: (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol(1335017-70-3)

Safety Data

• Hazardous Substances Data: 1335017-70-3(Hazardous Substances Data)

Upstream product

• 14438-63-2 1-(2,5-dimethoxyphenyl)-2-nitroethanol 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 75-52-5 nitromethane 

Relevant articles and documents

Production of (S)-β-Nitro Alcohols by Enantioselective C?C Bond Cleavage with an R-Selective Hydroxynitrile Lyase

Hydroxynitrile lyase (HNL)-catalysed stereoselective synthesis of β-nitro alcohols from aldehydes and nitroalkanes is considered an efficient biocatalytic approach. However, only one S-selective HNL—Hevea brasiliensis (HbHNL)—exists that is appropriate for the synthesis of (S)-β-nitro alcohols from the corresponding aldehydes. Further, synthesis catalysed by HbHNL is limited by low specific activity and moderate yields. We have prepared a number of (S)-β-nitro alcohols, by kinetic resolution with the aid of an R-selective HNL from Arabidopsis thaliana (AtHNL). Optimization of the reaction conditions for AtHNL-catalysed stereoselective C?C bond cleavage of racemic 2-nitro-1-phenylethanol (NPE) produced (S)-NPE (together with benzaldehyde and nitromethane, largely from the R enantiomer) in up to 99 % ee and with 47 % conversion. This is the fastest HNL-catalysed route known so far for the synthesis of a series of (S)-β-nitro alcohols. This approach widens the application of AtHNL for the synthesis not only of (R)- but also of (S)-β-nitro alcohols from the appropriate substrates. Without the need for the discovery of a new enzyme, but rather by use of a retro-Henry approach, it was used to generate a number of (S)-β-nitro alcohols by taking advantage of the substrate selectivity of AtHNL.

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

The Cu(I)-based complex prepared from (S)-2-(furan-2-yl-methylamino)-2- phenylethanol (5c) and CuCl was used as catalyst in enantioselective Henry reactions of arylaldehydes and nitromethane, which gave 89% ee and 95% yield at ambient temperature. The proposed catalytic cycle of an asymmetric Henry reaction was suggested. TUeBITAK.