5447-98-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2-methyl-1-nitropropan-2-ol is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical properties.
Used as a Solvent in Organic Reactions:
2-methyl-1-nitropropan-2-ol is used as a solvent in organic reactions, facilitating the process and improving the efficiency of the reactions.
Used in Propellants and Explosives:
2-methyl-1-nitropropan-2-ol is used as a stabilizer in propellants and explosives due to its ability to act as a fuel and oxygen donor, enhancing the performance and safety of these materials.
Used in Dye Intermediates and Rubber Chemicals Production:
2-methyl-1-nitropropan-2-ol is used in the production of dye intermediates and rubber chemicals, contributing to the development of various industrial products.
Safety Precautions:
2-methyl-1-nitropropan-2-ol is considered a hazardous material and should be handled with care due to its potential for explosion and irritation to the skin, eyes, and respiratory system. Proper safety measures and handling procedures should be followed to minimize risks.

Upstream product

• 75-52-5 nitromethane 
• 110-58-7 n-Pentylamine 
• 67-64-1 acetone 
• 121-44-8 triethylamine 
• 124-41-4 sodium methylate 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 1606-30-0 1-Nitro-2-methyl-1-propen 
• 123-91-1 1,4-dioxane 
• 10544-72-6 dinitrogen tetraoxide 
• 60-29-7 diethyl ether 
• 141-78-6 ethyl acetate 
• 14202-69-8 2-methyl-1-nitro-2-(nitroxy)propane 

Downstream Products

• 762-98-1 2,2-dimethyl-1,3-dinitropropane 
• 20867-84-9 2-Acetoxy-2-methyl-1-nitro-propan 
• 1606-30-0 1-Nitro-2-methyl-1-propen 
• 75-52-5 nitromethane 
• 67-64-1 acetone 

Relevant academic research and scientific papers

Ketones as electrophile in nitroaldol reaction: Synthesis of β,β-disubstituted-1,3-dinitroalkanes and allylic nitro compounds

β,β-Disubstituted-1,3-dinitro compounds were obtained exclusively with an overall yield of 83% through a domino nitroaldol/elimination/1,4-addition process, when excess nitromethane was added to cyclohexanone or butanone using DBU (1,8-diazabicyclo[5.4.0]

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.

Rapid microwave-assisted Henry reaction in solvent-free processes

The solvent-free Henry reactions of nitromethane with a series of carbonyl compounds were studied under microwave irradiation. By using different bases and Lewis acids, the solvent-free nitroaldol reaction of aldehydes were realized under microwave condition, affording the corresponding adducts with high yields. Particularly, aliphatic ketones, which were hardly carried out this reaction, could be the reaction substrates in the nitroaldol reactions by employment of 1,4-diazabicyclo[2.2.2]octane (DABCO) under a similar conditions, giving the corresponding adducts with moderate to good yields. Georg Thieme Verlag Stuttgart.

Kinetics and mechanisms of the gas-phase elimination of 2-substituted primary, secondary and tertiary hydroxy groups in nitroalkanes

The kinetics of the gas-phase elimination of several 2-substituted primary, secondary and tertiary hydroxy groups in nitroalkanes were determined in a static reaction system over the temperature range 220-400°C and pressure range of 29-235 Torr. The reactions, in seasoned vessels, are homogeneous and unimolecular and obey a first-order rate law. The presence of secondary and tertiary hydroxy substituent at the 2-position of the nitro group in nitroalkanes leads to a retro-aldol type of decomposition. The mechanism may be rationalized in terms of a six-membered cyclic transition state to give the corresponding aldehyde or ketone and the nitroalkane, respectively. However, some of the primary 2-hydroxy groups in nitroalkanes undergo a dehydration process with very limited isomerization to the corresponding alkyl nitrate. The mechanism of dehydration is believed to proceed through a six-membered rather than the already reported four-membered cyclic transition state to give the nitroalkene and water. In the case of the primary hydroxy substituent in 2-methyl-2-nitro-1-pentanol, the products of elimination are HNO2 gas and 3-hydroxy-2-methyl-1-propene. This reaction is rationalized in terms of a four-membered cyclic transition state type of mechanism. The kinetic and thermodynamic parameters of the hydroxynitroalkane substrates are presented and discussed. Copyright 2004 John Wiley & Sons, Ltd.

P(RNCH2CH2)3N: An Efficient Promoter for the Nitroaldol (Henry) Reaction

The use of catalytic amounts of the proazaphosphatranes P(MeNCH2CH2)3N, P(i-PrNCH2CH2)3N and P(HNCH2CH2)(i-PrNCH2CH2) 2N as nonionic bases in the reaction of nitroalkanes with carbonyl compounds is reported. The reaction proceeds at room temperature in the presence of 2.2 equiv of magnesium sulfate to produce the corresponding β-nitroalkanols in generally superior yields. Aldehydes react quantitatively in 5-60 min, whereas ketones require up to 3 h to react with nitromethane and up to 7 h for the reaction of ketones with higher nitroalkanes.

A total synthesis of isosolanone

Nitroaldol reaction of acetone with nitromethane in the presence of base to give a nitroalcohol 3, followed by acetylation, and subsequent reduction of the resultant acetate 4 with NaBH4 gave 2-methyl-1 nitropropane 5. Michael reaction of 5 in base with acrylonitrile to give nitronitrile 6, and Nef conversion of the nitro group resulted in the corresponding ketonic nitrile 7. Wittig olefination of the ketonic nitrile with 3-methyl-2-butenyl triphenylphosphonium bromide 8 gave dienenitrile 9, which upon treatment with MeLi, followed by acidic work up, provided isosolanone 2.