14438-63-2

Usage

Structure

Nitroethanol derivative with a phenyl ring, methoxy substituents, and a nitro group attached to a two-carbon ethyl chain

Usage

Intermediate in the synthesis of various pharmaceuticals and organic compounds

Biological activities

Potential vasodilator and use in the treatment of cardiovascular diseases

Safety precautions

Proper handling and safety measures should be taken to prevent potential hazards

Upstream product

• 75-52-5 nitromethane 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 14367-89-6 1-(2,5-dimethoxy-phenyl)-2-nitro-ethanone 
• 3600-87-1 desglymidodrine 
• 1335017-70-3 (1R)-1-(2,5-dimethoxyphenyl)-2-nitroethanol 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 919797-20-9 2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol 
• 108536-18-1 β-dimethoxy-2,5 phenyl nitro ethylene 
• 14547-37-6 1-(2,5-dimethoxy-phenyl)-3-morpholin-4-yl-2-nitro-propan-1-one 

Relevant academic research and scientific papers

Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes

An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.

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.

Salen-Based Covalent Organic Framework

The Salen unit represents one of the most important ligands in coordination chemistry. We report herein the first example of a Salen-based covalent organic framework (COF), in which both the construction of the COF structure and the functionalization with Salen moieties have been realized in a single step. Due to its structural uniqueness, the obtained COF material, Salen-COF, possesses high crystallinity and excellent stability. Based on this, a series of metallo-Salen-based COFs were prepared via metalation for further applications.

Preparation method of 1-(2,5-dimethoxy phenyl)-2-aminoethanol

The invention provides a preparation method of hydrochloric acid midodrine intermediate 1-(2,5-dimethoxy phenyl)-2-aminoethanol, comprising the steps of adopting 2,5-dimethoxy benzaldehyde as the raw material to condense with nitromethane under the effect of alkali to obtain 1-(2,5-dimethoxy phenyl)-2-nitroethanol, reducing 1-(2,5-dimethoxy phenyl)-2-nitroethanol with a boron reductant to obtain 1-(2,5-dimethoxy phenyl)-2-aminoethanol. The preparation method of 1-(2,5-dimethoxy phenyl)-2-aminoethanol has the advantages of being mild in reaction conditions, simple in the operation process, high in yield, environment-friendly and low in production cost, and is applicable to industrial production.

(2S,5R)-2-Methylaminomethyl-1-methyl-5-phenylpyrrolidine, a chiral diamine ligand for copper(ii)-catalysed Henry reactions with superb enantiocontrol

A cis-2-aminomethyl-5-phenylpyrrolidine, which is easily available from methyl Boc-l-pyroglutamate, was found to be a highly efficient chiral ligand for Cu(ii)-catalysed Henry reactions. Excellent yields (>90%) and superb levels of enantiocontrol (98.5-99.6% ee) were reached with aromatic, heteroaromatic, vinylic, and aliphatic aldehydes (36 examples). This journal is the Partner Organisations 2014.

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.

Crown ether complex cation ionic liquids: Preparation and applications in organic reactions

A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.

Heterogeneous catalysts in the preparation of 2-aryl-1,3-dinitropropanes from β-nitrostyrenes or benzaldehydes

The use of heterogeneous basic catalysts (KF, NaHCO3) in the preparation of 2-Aryl-1,3-dinitropropanes from β-nitrostyrenes or benzaldehydes is described, with one example followed kinetically by HPLC analysis of aliquots of the reaction.