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:2-Methyl-2-nitrosopropane

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| ImageFile = 2-methyl-2-nitrosopropane-2D-skeletal.png

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| ImageSize = 100

| ImageName = Skeletal formula of 2-methyl-2-nitrosopropane

| ImageFile2 = 2-methyl-2-nitrosopropane-3D-balls.png

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| ImageName2 = Ball and stick model of 2-methyl-2-nitrosopropane

| PIN = 2-Methyl-2-nitrosopropane{{Cite web|title=tert-nitrosobutane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=23272&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=7 May 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}

| OtherNames = tert-Nitrosobutane

|Section1={{Chembox Identifiers

| Abbreviations = MNP{{cite journal|vauthors=Singh RJ, Hogg N, Joseph J, Kalyanaraman B|title=Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production|journal=FEBS Lett|date=1995-02-20|volume=360|issue=1|pages=47–51|doi=10.1016/0014-5793(95)00065-h|pmid=7875299|url=https://febs.onlinelibrary.wiley.com/doi/epdf/10.1016/0014-5793(95)00065-H}}

| CASNo = 917-95-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = JGX6N17V2U

| PubChem = 23272

| ChemSpiderID = 21764

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| MeSHName = tert-nitrosobutane

| SMILES = CC(C)(C)N=O

| StdInChI = 1S/C4H9NO/c1-4(2,3)5-6/h1-3H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LUQZKEZPFQRRRK-UHFFFAOYSA-N

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|Section2={{Chembox Properties

| C=4 | H=9 | N=1 | O=1

| Appearance = Blue liquid

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|Section3={{Chembox Related

| OtherCompounds = {{Unbulleted list|Ethylamine|Ethylenediamine|Propylamine|Isopropylamine|1,2-Diaminopropane|1,3-Diaminopropane|Isobutylamine|tert-Butylamine|n-Butylamine|sec-Butylamine|Putrescine}}

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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.

Preparation and structure

Many strong oxidants convert tert-butylamine to the nitroso compound, but none do so in high yield.{{cite encyclopedia|doi=10.1002/047084289X.rn02280|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|article=2‑methyl-2‑nitroso­propane and 2‑methyl-2‑nitroso­propane dimer|first1=Viet D.|last1=Nguyen|first2=Vu T.|last2=Nguyen|first3=Oleg V.|last3=Larionov|date=23 Jan 2020}} Consequently, t-BuNO is prepared by the following "oscillatory redox" sequence:{{OrgSynth|first1=A. |last1=Calder |first2=A. R. |last2=Forrester |first3=S. P. |last3=Hepburn |title=2-Methyl-2-nitrosopropane and Its Dimer |collvol=6 |collvolpages=803 |volume=52 |page=77 |prep=cv6p0803}}

:(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.{{cite journal

| journal = J. Org. Chem.

| title = tert-Alkylnitroso compounds. Synthesis and dimerization equilibriums

| pages = 3055–3056

| volume = 36

| year = 1971

| author = John C. Stowell

| url =

| doi = 10.1021/jo00819a038

| issue = 20

}}

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.{{cite journal

|journal=J. Biol. Chem.

|title=ESR Spin-trapping of a Protein-derived Tyrosyl Radical from the Reaction of Cytochrome c with Hydrogen Peroxide

|pages=15498–15503

|issue=26

|volume=271

|year=1996

|author1=David P. Barr

|author2=Michael R. Gunther

|author3=Leesa J. Deterding

|author4=Kenneth B. Tomer

|author5=Ronald P. Mason

|url=http://www.jbc.org/cgi/content/abstract/271/26/15498

|doi=10.1074/jbc.271.26.15498

|archiveurl=https://web.archive.org/web/20081028161706/http://www.jbc.org/cgi/content/abstract/271/26/15498

|archivedate=2008-10-28

|url-status=live

|accessdate=2009-04-06

|pmid=8663160

|doi-access=free

}}

It has also been used in organic chemistry as electrophile to transform sulfones into aldehydes.{{Cite journal|last1=Rodrigo|first1=Eduardo|last2=Alonso|first2=Inés|last3=Cid|first3=M. Belén|date=2018-09-21|title=A Protocol To Transform Sulfones into Nitrones and Aldehydes|journal=Organic Letters|volume=20|issue=18|pages=5789–5793|doi=10.1021/acs.orglett.8b02483|pmid=30207472|s2cid=52186913 |issn=1523-7060}}

MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism.{{Cite journal

|author1=Dmitry F Grishin |author2=Lyudmila L Semyonycheva |author3=Elena V Kolyakina | title= 2-Methyl-2-nitrosopropane as a new regulator of the polymer chain growth

| journal= Mendeleev Communications

| year = 1999

| volume=9

| issue=6

| pages = 250–251

| doi= 10.1070/mc1999v009n06ABEH001161

}}

See also

References

{{Reflist}}

{{DEFAULTSORT:Methyl-2-Nitrosopropane, 2-}}

Category:Nitroso compounds

Category:Tert-butyl compounds