2-Methyl-2-nitrosopropane

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2-Methyl-2-nitrosopropane
Skeletal formula of 2-methyl-2-nitrosopropane 2-methyl-2-nitrosopropane-2D-skeletal.png
Skeletal formula of 2-methyl-2-nitrosopropane
Ball and stick model of 2-methyl-2-nitrosopropane 2-methyl-2-nitrosopropane-3D-balls.png
Ball and stick model of 2-methyl-2-nitrosopropane
Names
Preferred IUPAC name
2-Methyl-2-nitrosopropane [1]
Other names
tert-Nitrosobutane
Identifiers
3D model (JSmol)
AbbreviationsMNP [2]
ChemSpider
MeSH tert-nitrosobutane
PubChem CID
UNII
  • InChI=1S/C4H9NO/c1-4(2,3)5-6/h1-3H3 Yes check.svgY
    Key: LUQZKEZPFQRRRK-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)N=O
Properties
C4H9NO
Molar mass 87.122 g·mol−1
AppearanceBlue liquid
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 in chemical research as a spin trap, i.e. it binds to radicals.

Contents

Preparation and structure

Many strong oxidants convert tert-butylamine to the nitroso compound, but none do so in high yield. [3] Consequently, t-BuNO is prepared by the following "oscillatory redox" sequence: [4]

(CH3)3CNH2 → (CH3)3CNO2
(CH3)3CNO2 → (CH3)3CNHOH
(CH3)3CNHOH → (CH3)3CNO

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. [5]

Reactions

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. [6] It has also been used in organic chemistry as electrophile to transform sulfones into aldehydes. [7]

MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism. [8]

See also

References

  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. ↑ Singh RJ, Hogg N, Joseph J, Kalyanaraman B (1995-02-20). "Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production". FEBS Lett. 360 (1): 47–51. doi:10.1016/0014-5793(95)00065-h. PMID   7875299.
  3. ↑ Nguyen, Viet D.; Nguyen, Vu T.; Larionov, Oleg V. (23 Jan 2020). "2‑methyl-2‑nitroso­propane and 2‑methyl-2‑nitroso­propane dimer". Encyclopedia of Reagents for Organic Synthesis . doi:10.1002/047084289X.rn02280.
  4. ↑ Calder, A.; Forrester, A. R.; Hepburn, S. P. "2-Methyl-2-nitrosopropane and Its Dimer". Organic Syntheses . 52: 77; Collected Volumes, vol. 6, p. 803.
  5. ↑ John C. Stowell (1971). "tert-Alkylnitroso compounds. Synthesis and dimerization equilibriums". J. Org. Chem. 36 (20): 3055–3056. doi:10.1021/jo00819a038.
  6. ↑ David P. Barr; Michael R. Gunther; Leesa J. Deterding; Kenneth B. Tomer; 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 2008-10-28. Retrieved 2009-04-06.
  7. ↑ Rodrigo, Eduardo; Alonso, Inés; Cid, M. Belén (2018-09-21). "A Protocol To Transform Sulfones into Nitrones and Aldehydes". Organic Letters. 20 (18): 5789–5793. doi:10.1021/acs.orglett.8b02483. ISSN   1523-7060. PMID   30207472. S2CID   52186913.
  8. ↑ 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.
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