Diazald

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title: "Diazald" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sulfonamides", "nitroso-compounds", "alkyl-substituted-benzenes"] topic_path: "general/sulfonamides" source: "https://en.wikipedia.org/wiki/Diazald" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|ImageFile = N-Methyl-N-nitroso-p-toluenesulfonamide.svg |ImageSize = 200px |PIN = N,4-Dimethyl-N-nitrosobenzene-1-sulfonamide |OtherNames = N-Methyl-N-nitroso-4-methylbenzenesulfonamide; N-Methyl-N-nitroso-p-toluenesulphonamide; N-Methyl-N-nitroso-4-methylbenzenesulphonamide |Section1 = {{Chembox Identifiers |CASNo = 80-11-5 |CASNo_Ref = |UNII_Ref = |UNII = K3089966LA |EINECS = 201-252-6 |PubChem = 6628 |ChemSpiderID = 6376 |SMILES = Cc1ccc(cc1)S(=O)(=O)N(C)N=O |InChI = 1/C8H10N2O3S/c1-7-3-5-8(6-4-7)14(12,13)10(2)9-11/h3-6H,1-2H3 |InChIKey = FFKZOUIEAHOBHW-UHFFFAOYAJ |StdInChI = 1S/C8H10N2O3S/c1-7-3-5-8(6-4-7)14(12,13)10(2)9-11/h3-6H,1-2H3 |StdInChIKey = FFKZOUIEAHOBHW-UHFFFAOYSA-N |MeSHName = C418734 |Section2 = {{Chembox Properties |C=8|H=10|N=2|O=3|S=1 |Appearance = Light yellow solid |MeltingPtC = 61-62 |Section3 = {{Chembox Hazards |ExternalSDS = External MSDS |MainHazards = Skin sensitiser, irritant, explosive | NFPA-F = 0 | NFPA-H = 2 | NFPA-R = 3

Diazald (N-methyl-N-nitroso-p-toluenesulfonamide) is used as a relatively safe and easily handled precursor to diazomethane, which is toxic and unstable. Since its introduction in 1954, Diazald has become the favored commercially available precursor for the synthesis of diazomethane, compared to reagents like N-methyl*-N*-nitrosourea and N-methyl-N'-nitro-N-nitrosoguanidine, which are less thermally stable and more toxic and mutagenic, respectively.

Upon the addition of a base such as sodium hydroxide or potassium hydroxide and mild heating (65–70 °C) in a mixture of water, diethyl ether, and a high boiling polar cosolvent (e.g., diethylene glycol monomethyl ether), the N-nitrososulfonamide undergoes successive elimination reactions to produce diazomethane (which is codistilled as an ethereal solution) as well as a p-toluenesulfonate salt as a byproduct, according to the following mechanism: ::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/0b/DiazaldMechanism.png" caption="issn=0002-7863}}" alt=""] ::

Notes

References

References

  1. [http://feql.wsu.edu/MSDS/Diazald.pdf External MSDS], Sigma Aldrich
  2. "Diazald in Chemical Synthesis". [[Sigma-Aldrich]].
  3. (January 1954). "A new method for the preparation of diazomethane". [[Recueil des Travaux Chimiques des Pays-Bas]].
  4. (1956). "Diazomethane".
  5. (January 1954). "Mechanism of the alkaline decomposition of sulphonylnitrosamides: (IInd communication on sulphonylnitrosamides)". [[Recueil des Travaux Chimiques des Pays-Bas]].
  6. (1983). "The Preparation and Reactions of Diazomethane". [[Aldrichimica Acta]].
  7. (2010). "Organic Mechanisms: Reactions, Stereochemistry and Synthesis". Springer Berlin Heidelberg.
  8. Zhu, Xiao-Qing. (March 2005). "Determination of N−NO Bond Dissociation Energies of N-Methyl-N-nitrosobenzenesulfonamides in Acetonitrile and Application in the Mechanism Analyses on NO Transfer". Journal of the American Chemical Society.

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sulfonamidesnitroso-compoundsalkyl-substituted-benzenes