39220-86-5

Usage

Properties

1. Chemical formula: C10H13NO5
2. Physical form: White to off-white crystalline powder
3. Functional groups: Nitro, alcohol, and methoxy groups attached to a benzene ring
4. Reactivity: Wide range of reactivity in organic chemistry
5. Usage: Synthesis of pharmaceuticals and organic compounds
6. Potential health hazards: Handle with care and follow safety precautions

Physical form

White to off-white crystalline powder

Functional groups

Nitro, alcohol, and methoxy groups attached to a benzene ring

Reactivity

Wide range of reactivity in organic chemistry

Usage

Synthesis of pharmaceuticals and organic compounds

Safety precautions

Handle with care due to potential health hazards

Upstream product

• 75-52-5 nitromethane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 6924-15-8 2-amino-1-(3,4-dimethoxy-phenyl)-ethanol 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 46729-91-3 1-(3,4-dimethoxyphenyl)-2-nitroethan-1-one 
• 4876-02-2 N-(3,4-dimethoxyphenethyl)-phenyl acetamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 39628-26-7 N-(3,4-Dimethoxy-β-phenylaethyl)-acetoxyacetamid 
• 100619-46-3 N-(3,4-dimethoxyphenethyl)methoxyacetamide 
• 56997-75-2 N-(3,4-dimethoxyphenethyl)-α-bromoacetamide 
• 4876-00-0 1-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1391133-80-4 N-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-4-(1,3-dioxo-1,3-dihydro-2H-isoindolin-2-yl)butanamide 

Relevant academic research and scientific papers

Waste-to-useful: A biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction

Owing to the depletion of resources coupled with increasing waste generation, the conversion of waste biomass to value-added materials has gained interest. Here, we report for the first time the application of Musa acuminata (banana) peel ash (MAPA) as a heterogeneous catalyst for C-C bond formation via a Henry reaction under solvent-free conditions at ambient temperature. The catalyst was well characterized using different analytical techniques like FT-IR, SEM, TEM-EDS, XRD, XRF, XPS, BET and TGA, along with basicity determination by a Hammett indicator test and titration method. An excellent yield of nitroalcohol was obtained within 15-30 minutes. No dehydrated product was observed. The catalyst used in these studies has the advantage of being a waste material and is hence low-cost, easily prepared, recyclable and environmentally friendly. In addition, the use of a biogenic renewable catalyst, its atom economy, and room temperature and solvent-free reaction conditions and the avoidance of column chromatography make the protocol highly significant from green and sustainable chemistry perspectives.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Diaminosilane-functionalized on silicate-stabilised hydrotalcite (MA-HTSi-DA): As potential catalyst for nitro-aldol condensation

Diaminosilane was introduced into silicate-anion-intercalated hydrotalcite (HT-Si) using a post-synthesis method. The resulting functionalized materials possess surface basicity. The textural properties of the functionalized materials were systematically investigated through powder XRD, FTIR and MAS-NMR studies. The diamine-functionalized materials showed very good catalytic activity for the nitro-aldol condensation of benzaldehyde and nitromethane under solvent-free conditions. The materials showed comparable catalytic activity upon recycling.

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.

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

(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.

Henry reaction in aqueous media at neutral pH

An efficient method for the synthesis of β-nitro alcohols from nitro alkanes and aldehydes in aqueous phosphate buffer under neutral pH conditions at room temperature is reported. In the case of higher nitro alkanes, the reaction showed very good diastereoselectivity to give syn β-nitro alcohols in preference to their anti products. Copyright

Ethyl acrylate conjugated polystyryl-diphenylphosphine - An extremely efficient catalyst for Henry reaction under solvent-free conditions (SolFC)

Over the last few decades, the fast-growing development of polymer supported reagents has led to the synthesis of a variety of reagents on solid support. Some of the major advantages of using such reagents are that they are less hygroscopic, easy to recover, and can be recycled. Here, we have demonstrated that in situ generated ethyl acrylate conjugated polystyryl-diphenylphosphine (PDPP-EA) derived from the reaction of a mixture of polystyryl-diphenylphosphine and ethyl acrylate in a stoichiometric ratio can efficiently catalyze the synthesis of β-nitroalcohols from the reaction of aldehydes and nitroalkanes under solvent-free conditions (SolFC).

One-pot solid phase synthesis of (E)-nitroalkenes

An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.

Direct Henry reactions with modified calcium oxide as solid catalyst

Commercial CaO was modified simply with benzyl bromide. The modified CaO had good water resistance, and characterization by FTIR and TG revealed the modifier was chemically bonded to the CaO surface. Commercial CaO and CaO modified with benzyl bromide were investigated as catalysts for the Henry reaction between benzaldehyde and nitromethane. It was found that the catalytic activity of the modified CaO was greatly improved, with high conversion of benzaldehyde to the (E)-phenyl nitroolefin and 1-phenyl-2-nitroethanol, and with different selectivity from commercial CaO. The effect of modification and reaction conditions on yield, selectivity, and mechanism were studied thoroughly.