2-Methyl-2-nitrosopropane

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2-Methyl-2-nitrosopropane
Skeletal formula of 2-methyl-2-nitrosopropane
Ball and stick model of 2-methyl-2-nitrosopropane
Identifiers
Abbreviations NMP[citation needed]
CAS number 917-95-3 N
PubChem 23272
ChemSpider 21764 YesY
MeSH tert-nitrosobutane
Jmol-3D images Image 1
Properties
Molecular formula C4H9NO
Molar mass 87.12 g mol−1
Appearance Blue liquid
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane) is the organic compound with the formula (CH3)3CNO. It is a blue liquid that is used as a spin-trap in chemical research, i.e. it binds to radicals.

Preparation and structure[edit]

It is prepared by oxidation of (CH3)3CNH2 using hydrogen peroxide in the presence of sodium tungstate as a catalyst.[2] The freshly distilled compound is a blue volatile liquid. Like other nitroso compounds, it features a bent C-N=O linkage. Upon standing at room temperature, the blue liquid converts to the colourless solid that is the dimer (m.p. 74-75 °C). In solution, this dimer quickly reverts to the blue monomer.[3]

Reactions[edit]

It can be used as a spin trap. This molecule traps unstable free radicals to form stable paramagnetic nitroxide radicals that can be detected and analyzed by electron spin resonance spectroscopy. It is particularly useful for trapping carbon-centered tyrosyl radicals.[4]

MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism.[5]

See also[edit]

References[edit]

  1. ^ "tert-nitrosobutane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 7 May 2012. 
  2. ^ A. Calder, A. R. Forrester, and S. P. Hepburn 2-Methyl-2-nitrosopropane and Its Dimer Organic Syntheses, Coll. Vol. 6, p.803; Vol. 52, p.77. Link
  3. ^ John C. Stowell (1971). "tert-Alkylnitroso compounds. Synthesis and dimerization equilibriums". J. Org. Chem. 36 (20): 3055–3056. doi:10.1021/jo00819a038. 
  4. ^ David P. Barr, Michael R. Gunther, Leesa J. Deterding, Kenneth B. Tomer, and Ronald P. Mason (1996). "ESR Spin-trapping of a Protein-derived Tyrosyl Radical from the Reaction of Cytochrome c with Hydrogen Peroxide". J. Biol. Chem. 271 (26): 15498–15503. doi:10.1074/jbc.271.26.15498. PMID 8663160. Archived from the original on 2009-05-14. Retrieved 2009-04-06. 
  5. ^ Dmitry F Grishin, Lyudmila L Semyonycheva, Elena V Kolyakina (1999). "2-Methyl-2-nitrosopropane as a new regulator of the polymer chain growth". Mendeleev Communications 9 (6): 250–251. doi:10.1070/mc1999v009n06ABEH001161.