22920-77-0

Usage

Physical state

Pale yellow oil

Odor

Sharp, unpleasant

Uses

Intermediate in the synthesis of various organic compounds, production of pharmaceuticals, agrochemicals, and other fine chemicals, solvent in some chemical reactions, reagent in organic synthesis

Hazards

Toxic if ingested, inhaled, or absorbed through the skin, potential explosion hazard

Handling and storage

Handle with care and store appropriately.

Upstream product

• 3156-74-9 1-nitro-2-butanol 
• 75-52-5 nitromethane 
• 123-38-6 propionaldehyde 
• 54264-50-5 1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one 
• 4122-52-5 1-(1H-imidazol-1-yl)propan-1-one 
• 22755-24-4 sodium salt of nitromethane 

Downstream Products

• 36176-40-6 1-phenyl-1,2-butanedione-1-oxime 
• 932-90-1 Benzaldoxime 
• 112825-85-1 C₁₆H₁₇NO₂S₂ 
• 110097-28-4 (Z)-phenyl N-hydroxy-2-oxobutanimidothioate 
• 110097-30-8 N-hydroxy-2-oxobutanimidoyl chloride 
• 108661-54-7 1-amino-2-butanone hydrochloride 
• 34555-48-1 (1-nitromethyl-propyliden)-aniline 
• 110097-30-8 2-oxo-butyrohydroximoyl chloride 

Relevant academic research and scientific papers

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.

Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330

Enantiomerically pure β- and γ-nitro alcohols were prepared from their respective nitro ketones by asymmetric reduction mediated by the biocatalyst, Candida parapsilosis ATCC 7330 under optimized reaction conditions (ee up to >99%; yields up to 76%). This

Phenylation reaction of α-acylnitromethanes to give 1,2-diketone monooximes: Involvement of carbon electrophile at the position a to the nitro group

The generality and the effects of substituents on phenylation reactions of α-acylnitromethanes catalyzed by trifluoromethanesulfonic acid have been studied. α-Aroylnitromethanes afforded benzil monooximes in good yield. In the case of aliphatic α-acylnitromethane, a similar phenylation reaction proceeded, but the yield of the phenylated 1,2-dione monooxime was low. These phenylation reactions represent examples of the generation of carbocation electrophiles at the α-position of a nitro group. Georg Thieme Verlag Stuttgart - New York.

Reaction of 2-Nitroenamines and 2-Nitroalkenyl Sulfides with Ethyl Isocyanoacetate. A Novel Synthesis of 1-Hydroxypyrazoles

We have show that 1-hydroxypyrazoles can be prepared easily and regioselectively from the reaction of nitroenamines with ethyl isocyanoacetate. α,β-Unsaturated aci-nitronates are formed in the reaction and are then hydrolysed to give the products by quenching with acid.

Simple Preparation of α-Acyl α-Arylthio Oximes (N-Hydroxy-2-oxoalkanimidothioates): Ambident Reactivity of α-Nitro Ketones

A one-step synthesis of α-acyl α-phenylthio oximes by nucleophilic dehydration of α-nitro ketones is described.Treatment of the α-nitro ketones 7a-c (prepared by reaction of the sodium salt of nitromethane 6 with the acylimidazoles 5a-c) with thiophenol and titanium tetrachloride in the presence of triethylamine gave the phenyl N-hydroxy-2-oxoalkanimidothioates 4a-c in good yield.These products are potentially useful intermediates for the synthesis of analogues of the well known pesticides, methomyl, thiodicarb, and oxamyl.Interestingly, when the α-nitro ketones 7a-c are treated with thiophenol in the presence of boron trifluoride, only thioketalization is observed and the thioketals 8a-c are produced.The stereochemistry of the oxime hydroxyl in the crystal was shown to be syn to the phenylthio group, i.e., Z stereochemistry, by a single-crystal X-ray structure determination.A reasonable mechanistic explanation is presented to explain the reaction pathway.

Nitroacetylene Equivalents. Preparation and Cycloadditions of 2-Phenylsulphinyl-1-nitroalkenes

β-Phenylsulphinyl-nitro-alkenes (7) are readily prepared from acyl imidazoles and react as nitroacetylene equivalents in Diels-Alder reactions to give good yields of cycloadducts and their further products.

PREPARATION AND OXIDATION OF α-NITRO ALCOHOLS WITH SUPPORTED REAGENTS.

Preparation of 2-nitro alkanols has been achieved by condensation of aldehydes with nitroalkanes in the presence of alumina-supported potassium fluoride.Nitroketones are produced by oxidation of nitroalkanols with montmorillonite - supported chromium trioxide.