3156-74-9

Usage

Physical State

Colorless to pale yellow liquid

Odor

Slightly sweet

Chemical Class

Nitro alcohols

Primary Use

Intermediate in the synthesis of pharmaceuticals, agricultural chemicals, and other organic compounds

Secondary Use

Solvent for nitrocellulose, resins, and waxes

Hazardous

Yes, flammable and can cause irritation to skin, eyes, and respiratory system

Safety Protocols

Handle and store with caution, follow proper safety protocols.

Upstream product

• 75-52-5 nitromethane 
• 123-38-6 propionaldehyde 
• 6068-96-8 n-propyl hydroperoxide 
• 563-70-2 bromonitromethane 
• 106-98-9 1-butylene 
• 60-29-7 diethyl ether 
• 10544-72-6 dinitrogen tetraoxide 
• 27675-37-2 1-nitrobut-1-ene 

Downstream Products

• 27675-37-2 1-nitrobut-1-ene 
• 34487-38-2 (S)-1-Dimethylamino-2-butanol 
• 3760-97-2 (R)-1-Dimethylamino-2-butanol 
• 34487-37-1 (+/-)-1-Dimethylamino-2-butanol 
• 13552-21-1 2-hydroxy-butylamine 
• 22920-77-0 1-nitrobutan-2-one 
• 27675-37-2 (E)-1-nitrobut-1-ene 
• 115839-96-8 butyric acid-(1-nitromethyl-propyl ester) 

Relevant academic research and scientific papers

BICYCLIC KETONE COMPOUNDS AND METHODS OF USE THEREOF

The invention provides novel compounds having the general formula (I): (I) wherein R1, the A ring and the B ring are as described herein, pharmaceutical compositions including the compounds, and methods of using the compounds.

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.

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.

Organocatalytic Enantioselective Transfer Hydrogenation of β-Amino Nitroolefins

The asymmetric organocatalytic transfer hydrogenation of β-acylamino and β-tert-butyloxycarbonylamino nitroolefins has been successfully realised in excellent enantioselectivities and yields (up to >99% ee, 97% yield) with a simple thiourea catalyst and a Hantzsch ester as hydrogen source, giving a direct access to enantiomerically pure β-amino nitroalkanes. (Figure presented.).

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

Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: Controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams

An asymmetric intermolecular reaction between enals and nitroalkenes to yield δ-nitroesters has been developed, catalyzed by a novel chiral N-heterocyclic carbene. Key to this work was the development of a catalyst that favors the δ-nitroester pathway over the established Stetter pathway. The reaction proceeds in high stereoselectivity and affords the previously unreported syn diastereomer. We also report an operationally facile two-step, one-pot procedure for the synthesis of δ-lactams.

Catalytic asymmetric intermolecular stetter reaction of enals with nitroalkenes: Enhancement of catalytic efficiency through bifunctional additives

An asymmetric intermolecular Stetter reaction of enals with nitroalkenes catalyzed by chiral N-heterocyclic carbenes has been developed. The reaction rate and efficiency are profoundly impacted by the presence of catechol. The reaction proceeds with high selectivities and affords good yields of the Stetter product. Internal redox products were not observed despite of the protic conditions. The impact of catechol has been found to be general, facilitating far lower catalyst loadings than were previously achievable.

Enzyme-catalyzed Henry (nitroaldol) reaction

Transglutaminase was first used to catalyze Henry reactions of aliphatic, aromatic and hetero-aromatic aldehydes with nitroalkanes. The reactions were carried out at room temperature, and the corresponding nitro alcohols were obtained in yields up to 96%.