Methanesulfonyl azide

Methanesulfonyl azide
Names
	Other names Mesyl azide
Identifiers
CAS Number	1516-70-7;
3D model (JSmol)	Interactive image;
Abbreviations	MsN3
ChemSpider	483609;
PubChem CID	556271;
CompTox Dashboard (EPA)	DTXSID80339446 ;
	InChI InChI=1S/CH3N3O2S/c1-7(5,6)4-3-2/h1H3 Key: BHQIGUWUNPQBJY-UHFFFAOYSA-N;
	SMILES CS(=O)(=O)N=[N+]=[N-];
Properties
Chemical formula	CH3N3O2S
Molar mass	121.11 g·mol−1
Melting point	18 °C (64 °F; 291 K)
Boiling point	120 °C (248 °F; 393 K) decomposes
Solubility in water	Insoluble
Solubility	Ether, THF
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methanesulfonyl azide is the azide of methanesulfonic acid. It is used as a reagent for the production of diazo compounds.

Preparation

Methanesulfonyl azide can be prepared from methanesulfonyl chloride by reaction with sodium azide in ethanol^[1] or methanol.^[2] Preparation in situ is also possible, for example in acetonitrile, which can reduce explosion hazards.^[3]

Properties

Methanesulfonyl azide melts at 18 °C and decomposes at 120 °C.^[1] At low temperature, methanesulfonyl azide crystallizes in the triclinic crystal system in the space group P1 with lattice parameters a = 5.6240 Å; b = 5.9498 Å, c = 7.6329 Å, α = 72.216°, β = 70.897°, and γ = 88.601°, and two molecules per unit cell.^[1]

Mesyl azide is an antidote for hydrogen sulfide poisoning in mice.^[4]

Reactions

Methanesulfonyl azide is part of the sulfonyl azides, a family of reagents for diazo transfer. Within this family, methanesulfonyl azide is particularly simple and inexpensive to produce, while the reaction mixture is straightforward to purify.^[2]

The photolysis of methanesulfonyl azide in a matrix of argon or neon yields a short-lived nitrene.^[1] If methanesulfonyl azide is irradiated in the presence of a hydrocarbon, it forms methanesulfonyl amide, as well as N-substituted derivatives through reactions with the hydrocarbon.^[5]

Safety

Methanesulfonyl azide is fairly stable, but, like many other azides, it is toxic and still considered a potential explosive.^[3]

References

1 2 3 4 Deng, Guohai; Li, Dingqing; Wu, Zhuang; Li, Hongmin; Bernhardt, Eduard; Zeng, Xiaoqing (2016-07-21), "Methanesulfonyl Azide: Molecular Structure and Photolysis in Solid Noble Gas Matrices", The Journal of Physical Chemistry A, vol. 120, no. 28, pp. 5590–5597, Bibcode:2016JPCA..120.5590D, doi:10.1021/acs.jpca.6b05533, PMID 27383463
1 2 Taber, Douglass F.; Ruckle, Robert E.; Hennessy, Michael J. (October 1986), "Mesyl azide: a superior reagent for diazo transfer", The Journal of Organic Chemistry, vol. 51, no. 21, pp. 4077–4078, doi:10.1021/jo00371a034
1 2 Lynch, Denis; O’Mahony, Rosella M.; McCarthy, Daniel G.; Bateman, Lorraine M.; Collins, Stuart G.; Maguire, Anita R. (2019-06-16), "Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR", European Journal of Organic Chemistry, vol. 2019, no. 22, pp. 3575–3580, doi:10.1002/ejoc.201900184, hdl:10468/8205
↑ Howes, Laura (25 June 2019). "Data mining for a hydrogen sulfide antidote". Chemical and Engineering News. Vol. 97, no. 26. American Chemical Society. ISSN 0009-2347.
↑ Torimoto, Noboru; Shingaki, Tadao; Nagai, Toshikazu (February 1978), "Sensitized photolyses of methanesulfonyl azide in hydrocarbons", The Journal of Organic Chemistry, vol. 43, no. 4, pp. 631–633, doi:10.1021/jo00398a023

[:0-1] 1 2 3 4 Deng, Guohai; Li, Dingqing; Wu, Zhuang; Li, Hongmin; Bernhardt, Eduard; Zeng, Xiaoqing (2016-07-21), "Methanesulfonyl Azide: Molecular Structure and Photolysis in Solid Noble Gas Matrices", The Journal of Physical Chemistry A, vol. 120, no. 28, pp. 5590–5597, Bibcode:2016JPCA..120.5590D, doi:10.1021/acs.jpca.6b05533, PMID 27383463

[:1-2] 1 2 Taber, Douglass F.; Ruckle, Robert E.; Hennessy, Michael J. (October 1986), "Mesyl azide: a superior reagent for diazo transfer", The Journal of Organic Chemistry, vol. 51, no. 21, pp. 4077–4078, doi:10.1021/jo00371a034

[:2-3] 1 2 Lynch, Denis; O’Mahony, Rosella M.; McCarthy, Daniel G.; Bateman, Lorraine M.; Collins, Stuart G.; Maguire, Anita R. (2019-06-16), "Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR", European Journal of Organic Chemistry, vol. 2019, no. 22, pp. 3575–3580, doi:10.1002/ejoc.201900184, hdl:10468/8205

[4] Howes, Laura (25 June 2019). "Data mining for a hydrogen sulfide antidote". Chemical and Engineering News. Vol. 97, no. 26. American Chemical Society. ISSN 0009-2347.

[5] Torimoto, Noboru; Shingaki, Tadao; Nagai, Toshikazu (February 1978), "Sensitized photolyses of methanesulfonyl azide in hydrocarbons", The Journal of Organic Chemistry, vol. 43, no. 4, pp. 631–633, doi:10.1021/jo00398a023

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