Tetramethylazodicarboxamide

Tetramethylazodicarboxamide (also known as TMAD and diamide) is a reagent used in biochemistry for oxidation of thiols in proteins to disulfides.[2] It has also been used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate.[1]

Tetramethylazodicarboxamide[1]

Names
IUPAC name 3-(Dimethylcarbamoylimino)-1,1-dimethylurea
Other names Diamide; Tetramethyldiazenedicarboxamide; N,N,N′,N′-Tetramethylazoformamide 1,1'-Azobis(N,N-dimethylformamide); N,N,N′,N′-Tetramethylazobisformamide; Azodicarboxylic acid bis(dimethylamide); 1,1'-Azobis(N,N-dimethylformamide)
Identifiers
CAS Number	10465-78-8^Y
3D model (JSmol)	Interactive image
Abbreviations	TMAD
ChEBI	CHEBI:48958
ChemSpider	4510221
ECHA InfoCard	100.030.852
EC Number	233-951-7
PubChem CID	4278
UNII	86EQC90W32^Y
CompTox Dashboard (EPA)	DTXSID6040456
InChI InChI=1S/C6H12N4O2/c1-9(2)5(11)7-8-6(12)10(3)4/h1-4H3/b8-7+ Key: VLSDXINSOMDCBK-BQYQJAHWSA-N
SMILES CN(C)C(=O)N=NC(=O)N(C)C
Properties
Chemical formula	C6H12N4O2
Molar mass	172.188 g·mol^−1
Appearance	Yellow crystalline solid
Melting point	113 to 115 °C (235 to 239 °F; 386 to 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. Tetsuto Tsunoda, Hiroto Kaku, N,N,N′,N′-Tetramethylazodicarboxamide, in Encyclopedia of Reagents for Organic Synthesis, 2003, John Wiley & Sons, Ltd, doi:10.1002/047084289X.rn00274
2. CID 4278 from PubChem

Further reading

• Tsunoda, Tetsuto; Otsuka, Junko; Yamamiya, Yoshiko; Itô, Shô (1994). "N,N,N',N'-Tetramethylazodicarboxamide(TMAD), A New Versatile Reagent for Mitsunobu Reaction. Its Application to Synthesis of Secondary Amines". Chemistry Letters (3): 539. doi:10.1246/cl.1994.539.