5447-98-3

Basic information

• Product Name: 2-methyl-1-nitropropan-2-ol
• Synonyms: 2-Methyl-1-nitro-2-propanol; 2-Methyl-1-nitropropan-2-ol; 2-propanol, 2-methyl-1-nitro-
• CAS NO: 5447-98-3
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.1192
• Mol File: 5447-98-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 204.4°C at 760 mmHg
• Flash Point: 92.1°C
• Density: 1.135g/cm³
• Vapor Pressure: 0.0634mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: 2-methyl-1-nitropropan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-1-nitropropan-2-ol(5447-98-3)
• EPA Substance Registry System: 2-methyl-1-nitropropan-2-ol(5447-98-3)

Safety Data

• Hazardous Substances Data: 5447-98-3(Hazardous Substances Data)

Usage

General Description

2-methyl-1-nitropropan-2-ol, also known as methyl ethyl nitrocol, is a chemical compound with the molecular formula C4H9NO3. It is a pale yellow liquid at room temperature and is classified as a nitro alcohol. 2-methyl-1-nitropropan-2-ol is commonly used as a precursor in the synthesis of pharmaceuticals and agrochemicals, as well as a solvent in organic reactions. It is also used as a stabilizer in propellants and explosives due to its ability to act as a fuel and oxygen donor. Additionally, it has applications in the production of dye intermediates and rubber chemicals. 2-methyl-1-nitropropan-2-ol is considered to be a hazardous material and should be handled with care due to its potential for explosion and irritation to the skin, eyes, and respiratory system.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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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.

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.