N,N,N',N'-Tetramethylazodicarboxamide Chemical Properties

Melting point:

112 °C

Boiling point:

220.4±23.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

soluble in Methanol

form 

crystalline

pka

-0?+-.0.70(Predicted)

color 

yellow

BRN 

1910409

InChI

InChI=1S/C6H12N4O2/c1-9(2)5(11)7-8-6(12)10(3)4/h1-4H3/b8-7+

InChIKey

VLSDXINSOMDCBK-BQYQJAHWSA-N

SMILES

C(=O)(/N=N/C(=O)N(C)C)N(C)C

CAS DataBase Reference

10465-78-8(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

LQ1041000

F 

4.10

HS Code 

29270000

MSDS

• Language:English Provider:3-(N,N-Dimethylcarbamoylimido)-1,1-dimethylurea
• Language:English Provider:SigmaAldrich

N,N,N',N'-Tetramethylazodicarboxamide Usage And Synthesis

Description

N,N,N’,N’-Tetramethylazodicarboxamide (also named as Diamide, TMAD) is a reagent used for the oxidization of thiols in proteins. It is used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate. It can be used to titrate protein gluotathiolation to discriminate from other protein modifications.

References

N. S. Kosower, E. M. Kosower, Diamide: A oxidant probe for this, Methods in Enzymology, 1995, vol. 251, pp. 123133

Chemical Properties

Yellow crystals

Uses

Reported to be of use as a thiol oxidizing agent. Diamide has been used to titrate protein glutathiolation to discriminate from other oxidative protein modifications. Treatment increased protein glutathiolation in a concentration-dependent manner and had comparably little effect on protein-protein disulfide formation.

Definition

ChEBI: 1,1'-azobis(N,N-dimethylformamide) is a monoazo compound.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1652, 1973 DOI: 10.1021/jo00949a007

N,N,N',N'-Tetramethylazodicarboxamide(10465-78-8)Related Product Information

• Di-tert-Butyl azodicarboxylate
• N,N-Dimethylformamide
• Polyacrylamide
• Metformin
• PHTHALAMIDE
• 1,1'-(Azodicarbonyl)-dipiperidine
• Azodicarbonamide
• Pentamethyldiethylenetriamine
• Diethyl azodicarboxylate
• Dibenzyl azodicarboxylate
• Diisopropyl azodicarboxylate
• 1,8-Bis(dimethylamino)naphthalene
• N,N,N',N'-Tetraphenylbenzidine
• N,N,N',N'-TETRAMETHYLDIAMINOMETHANE
• AZODICARBOXYLIC BISMORPHOLIDE
• 1,1-DIMETHYLUREA
• Formamide
• N,N,N',N'-Tetramethylazodicarboxamide