Diazald

Diazald

Names
IUPAC name N-Methyl-N-nitroso-p-toluenesulfonamide
Other names Diazald, N-methyl-N-nitroso-4-methylbenzenesulphonamide
Identifiers
CAS Number	80-11-5
3D model (JSmol)	Interactive image
ChemSpider	6376
ECHA InfoCard	100.001.139
EC Number	201-252-6
MeSH	C418734
PubChem CID	6628
InChI InChI=1S/C8H10N2O3S/c1-7-3-5-8(6-4-7)14(12,13)10(2)9-11/h3-6H,1-2H3 Key: FFKZOUIEAHOBHW-UHFFFAOYSA-N InChI=1/C8H10N2O3S/c1-7-3-5-8(6-4-7)14(12,13)10(2)9-11/h3-6H,1-2H3 Key: FFKZOUIEAHOBHW-UHFFFAOYAJ
SMILES Cc1ccc(cc1)S(=O)(=O)N(C)N=O
Properties
Chemical formula	C8H10N2O3S
Molar mass	214.24 g mol−1
Appearance	light yellow solid
Melting point	61–62 °C (142–144 °F; 334–335 K)
Hazards
Main hazards	skin sensitiser, irritant, explosive
Safety data sheet	External MSDS
NFPA 704	0 2 3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Methyl-N-nitroso-p-toluenesulfonamide, known commercially as Diazald, is used as a relatively safe and easily handled precursor to diazomethane, which is toxic and unstable.

Upon the addition of a base such as sodium hydroxide or potassium hydroxide, an elimination reaction occurs to produce diazomethane as well as p-toluenesulfonic acid as a side product, according to the following mechanism: