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 known as Diamide or TMAD, is a reagent used for the oxidization of thiols in proteins. It is a yellow crystalline compound that can be used as a substitute for diethyl azodicarboxylate in the Mitsunobu reaction. Its ability to titrate protein glutathiolation allows for the discrimination of this modification from other protein modifications.

Uses

Used in Biochemistry Research:
N,N,N',N'-Tetramethylazodicarboxamide is used as a thiol oxidizing agent for studying protein glutathiolation. It helps in titrating protein glutathiolation to differentiate it from other oxidative protein modifications. The treatment with this reagent increases protein glutathiolation in a concentration-dependent manner and has minimal effects on protein-protein disulfide formation.
Used in the Mitsunobu Reaction:
In organic synthesis, N,N,N',N'-Tetramethylazodicarboxamide serves as a reagent in the Mitsunobu reaction, where it replaces diethyl azodicarboxylate. This substitution can be beneficial in certain reactions, providing an alternative for chemists to achieve specific synthetic goals.

References

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

Synthesis Reference(s)

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

Upstream product

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

Downstream Products

• 57049-50-0 C₁₃H₂₀N₄O₄S 
• 210963-56-7 benzyl (3R)-tert-butoxycarbonylamino-4-(5-cyano-2-iodophenoxy)butyric acid 
• 1226859-16-0 C₂₉H₃₂N₆O₃S 
• 1226859-15-9 C₂₉H₃₁N₇O₅S 

Relevant articles and documents

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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.