Methyldiazonium

Methyldiazonium
Names
	IUPAC name Methyldiazynium
Identifiers
CAS Number	20404-06-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:176914;
ChEMBL	ChEMBL2419248;
ChemSpider	103148;
KEGG	C20302;
PubChem CID	115287;
UNII	4MD529UV3B;
CompTox Dashboard (EPA)	DTXSID40174355 ;
	InChI InChI=1S/CH3N2/c1-3-2/h1H3/q+1 Key: RRJZCACJJKZDNV-UHFFFAOYSA-N;
	SMILES C[N+]#N;
Properties
Chemical formula	CH3N2+
Molar mass	43.048 g·mol−1
Acidity (pKa)	<10
Conjugate base	Diazomethane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Methyldiazonium is an organic compound consisting of a methyl group attached to a diazo group. This cation is the conjugate acid of diazomethane, with an estimated pK_a<10.^[1]

It is an intermediate in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of carboxylic acids to methyl esters and phenols to methyl ethers.^[2]

It has been implicated as the metabolite of N-nitrosodimethylamine responsible for the observed carcinogenicity of that compound.^[3]

References

^ Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pK_a of Brønsted acids controls their reactivity with diazo compounds". Chemical Communications. 52 (47): 7501–7504. doi:10.1039/C6CC03561B. PMID 27212133.
^ Kühnel, Erik; Laffan, David D. P.; Lloyd-Jones, Guy C.; Martínez del Campo, Teresa; Shepperson, Ian R.; Slaughter, Jennifer L. (2007). "Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane". Angew. Chem. Int. Ed. Engl. 46 (37): 7075–7078. doi:10.1002/anie.200702131. PMID 17691089.
^ Tricker, A. R.; Preussmann, R. (1991). "Carcinogenic N-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential". Mutation Research/Genetic Toxicology. 259 (3–4): 277–289. doi:10.1016/0165-1218(91)90123-4. PMID 2017213.

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[1] Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pK_a of Brønsted acids controls their reactivity with diazo compounds". Chemical Communications. 52 (47): 7501–7504. doi:10.1039/C6CC03561B. PMID 27212133.

[2] Kühnel, Erik; Laffan, David D. P.; Lloyd-Jones, Guy C.; Martínez del Campo, Teresa; Shepperson, Ian R.; Slaughter, Jennifer L. (2007). "Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane". Angew. Chem. Int. Ed. Engl. 46 (37): 7075–7078. doi:10.1002/anie.200702131. PMID 17691089.

[Tricker-3] Tricker, A. R.; Preussmann, R. (1991). "Carcinogenic N-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential". Mutation Research/Genetic Toxicology. 259 (3–4): 277–289. doi:10.1016/0165-1218(91)90123-4. PMID 2017213.

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