2224-37-5

Usage

Appearance

Colorless to yellow liquid

Odor

Slightly sweet, floral

Functional groups

Nitro group, hydroxyl group

Attached to

Pentane chain

Uses

Intermediate in synthesis of pharmaceuticals and agricultural chemicals, solvent in organic reactions, production of perfumes and flavors

Toxicity

Mildly toxic

Health effects

May cause irritation to skin, eyes, and respiratory system upon exposure

InChI:InChI=1/C5H11NO3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3

Upstream product

• 66022-60-4 1-nitropent-1-ene 
• 75-52-5 nitromethane 
• 123-72-8 butyraldehyde 
• 109-67-1 1-penten 

Downstream Products

• 66022-60-4 1-nitropent-1-ene 
• 3156-72-7 (1E)-1-nitropent-1-ene 
• 628-05-7 1-nitropentane 
• 5343-35-1 1-amino-2-hydroxy-pentane 
• 214679-10-4 (1S,2R,1'R)-(-)-N-<2-(1'-tert-butoxycarbonylaminomethylbutoxy)-1-methyl-2-phenylethyl>formamide 
• 214678-95-2 (1S,2R,1'R)-(-)-N-<1-methyl-2-(1'-nitromethylbutoxy)-2-phenylethyl>formamide 
• 214679-14-8 (2R)-(-)-1-tert-butoxycarbonylaminopentan-2-ol 
• 206068-37-3 (R)-2-((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-pentanoic acid 
• 251464-53-6 (R)-3-((R)-1-Aminomethyl-butyl)-4-phenyl-oxazolidin-2-one 
• 189350-19-4 (R)-3-((R)-1-Nitromethyl-butyl)-4-phenyl-oxazolidin-2-one 
• 2013-12-9 D-norvaline 

Relevant academic research and scientific papers

Tetrabutyldideazaporphyrin

McMurry coupling of a dibutylpyrrole diacrylaldehyde afforded an unstable tetrabutyldideazaporphyrin. Although this porphyrin analogue was highly unstable, proton NMR spectroscopy demonstrated that it retained a high degree of diatropic character.

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.

Synthesis, Characterization and Catalytic Activity of Magnetic KI@Fe3O4 Nanoparticles for Henry Reaction Under Solvent Free Conditions

Abstract: In this paper, we, for the first time reported the synthesis of KI loaded Fe3O4 nanoparticles (KI@Fe3O4 NPs) and investigated its applications in the synthesis of β-nitroalcohol via Henry reaction at room temperature under solvent-free conditions. The synthesized KI@Fe3O4 nanoparticle was characterized by SEM, HRTEM, XRD, XPS, EDX, VSM and FT-IR spectroscopy techniques. The XRD peaks at 2θ = 21.9, 25.65, 33.54, 36.35, 40.97, 42.81, 44.79, 54.43, 57.37, 58.83 and 63.13° corresponds to the formation of crystalline KI@Fe3O4 NPs. The activity of the catalyst by varying the amount of KI loading on Fe3O4 NPs was also investigated. Mild reaction conditions, good yield, short reaction time, solvent-free conditions, easy recoverability and recyclability of the nanocatalysts are the major advantages of our method. Graphical Abstract: [Figure not available: see fulltext.].

2-OXO-1,3-OXAZOLIDINYL IMIDAZOTHIADIAZOLE DERIVATIVES

The present invention relates to 2-oxo-1,3-oxazolidinyl imidazothiadiazole derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals.

Facile synthesis of 2-nitromethyl aromatic ketones by insertion of benzynes into the C-C bond of α-nitroketones

A facile method to synthesize 2-nitromethyl aromatic ketones was developed. In the method, benzyne was generated in situ for the insertion to α-Nitroketones in one pot to achieve 2-nitromethyl aromatic ketones under mild conditions. Aromatic and aliphatic α-nitroketones were applied in the reaction, and the results show that aliphatic α-nitroketones gave excellent yields (up to 96%), while aromatic α-nitroketones gave moderate yields. The synthesized 2-nitromethyl aromatic ketones could be potential substrates to synthesize isoindoles.

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.

Unprecedented Mechanism of an Organocatalytic Route to Conjugated Enynes with a Junction to Cyclic Nitronates

Conjugated enynes as well as cyclic nitronates are crucial building blocks for numerous natural products and pharmaceuticals. However, so far, no common and metal-free synthetic route to both conjugated enynes and cyclic nitronates has been reported. Herein, in situ NMR, labelling studies and theoretical calculations were combined to investigate the mechanism of the unusual triple bond formation towards conjugated enynes. Starting from nitroalkene dimers, first an isoxazolidine-2,5-diol derivative is formed as central intermediate. From this, enynes were generated by a combination of oxidation, dehydration, and retro 1,3-dipolar cycloaddition, whereas for nitronates a base induced intramolecular reorganization is proposed. While the product distribution could be controlled and high yields of nitronate were achieved, only medium to good yields for enynes were obtained due to polymerization losses. Nevertheless, we hope that these mechanistic investigations may provide a basis for further developments of organocatalytic or metal-free preparations of conjugated enynes and nitronates.

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.

Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid

DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.

Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid

DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.