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Tetramethylazodicarboxamide

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Tetramethylazodicarboxamide
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
3D model (JSmol)
Abbreviations TMAD
ChEBI
ChemSpider
ECHA InfoCard 100.030.852 Edit this at Wikidata
EC Number
  • 233-951-7
PubChem CID
UNII
CompTox Dashboard (EPA)
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
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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.
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