10465-78-8

Basic information

• Product Name: N,N,N',N'-Tetramethylazodicarboxamide
• Synonyms: AZODICARBOXYLIC ACID BIS[DIMETHYLAMIDE];DIAMIDE;DIAZINE-DICARBOXYLIC ACID BIS[N,N-DIMETHYLAMIDE];1,1'-AZOBIS(N,N'-DIMETHYLFORMAMIDE);1,1'-AZOBIS(N,N-DIMETHYLFORMAMIDE);N,N,N',N'-TETRAMETHYLAZODICARBAMIDE;N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE;1,1’-azobis(n,n-dimethyl-formamid
• CAS NO: 10465-78-8
• Molecular Formula: C₆H₁₂N₄O₂
• Molecular Weight: 172.19
• EINECS: 233-951-7
• Product Categories: Azodicarboxylates & Amides;Mitsunobu Reaction;Synthetic Organic Chemistry;proteinmod
• Mol File: 10465-78-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 112 °C
• Boiling Point: 220.4 °C at 760 mmHg
• Flash Point: 87.1 °C
• Appearance: yellow/crystalline
• Density: 1.13 g/cm³
• Storage Temp.: −20°C
• Solubility: soluble in Methanol
• PKA: -0?+-.0.70(Predicted)
• BRN: 1910409
• CAS DataBase Reference: N,N,N',N'-Tetramethylazodicarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetramethylazodicarboxamide(10465-78-8)
• EPA Substance Registry System: N,N,N',N'-Tetramethylazodicarboxamide(10465-78-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: LQ1041000
• F: 4.10
• Hazardous Substances Data: 10465-78-8(Hazardous Substances Data)

Usage

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.

Synthesis Reference(s)

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

Upstream product

• 124-40-3 dimethyl amine 
• 1972-28-7 diethylazodicarboxylate 
• 17696-89-8 1,2-bis(N,N-dimethylcarbamoyl)hydrazine 

Downstream Products

• 57049-50-0 C₁₃H₂₀N₄O₄S 
• 386216-83-7 (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepine 
• 313654-82-9 2-(2-Methoxyphenoxy)ethyl 3-(1-piperazinyl)-2-pyrazinyl ether 
• 402859-66-9 1-allyloxy-2-(3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)benzene 

Relevant articles and documents

-

-

-

-

Preparation method of azodicarbonamide

The preparation method comprises the following steps: Step S1, reacting hydrazine hydrochloride and dimethylbenzoyl chloride to form an intermediate. Step S2: The intermediate is subjected to an even nitridation reaction to give the azodicarboxamide. To the preparation method disclosed by the embodiment of the invention, the adopted raw material is high in safety, less in three wastes formed in production, and the obtained product can be obtained by effectively separating and drying, and pure product TMDA can be obtained without being purified again.

Oil-soluble bicarbamamide compounds

The oil-soluble azo compounds of this invention are useful as dispersants, corrosion inhibitors and anti-wear agents in lubricating oil and fuel compositions. The predominant oil-soluble azo reaction product may be represented by the following formulas: STR1 wherein R represents an oil-solubilizing, synthetic, polymeric organic radical containing at least 20 carbon atoms, Y is independently selected from the group consisting of --NR2 R3 and --SR4, R2, r3, and R4 are independently selected from hydrogen, alkyl, cycloalkyl, aryl, alkaryl and aralkyl, X is independently selected from oxygen, sulfur and =NR5, with the proviso that when X is =NR5, Y is --NR2 R3, R5 is selected from the group consisting of alkyl, cycloalkyl, aryl and alkaryl, Z represents a polyvalent organic radical having a valence of n and selected from hydrocarbon, oxahydrocarbon, azahydrocarbon and thiahydrocarbon radicals and their oxygenated and halogenated derivatives, E is a monovalent radical selected from alkyl, cycloalkyl, aralkyl, aryl, and alkaryl, and n is an integer from 2 to 5.