940868-64-4

Basic information

• Product Name: Di-2-Methoxyethyl azodicarboxylate
• Synonyms: Di-2-Methoxyethyl azodicarboxylate;Azodicarboxylic Acid Bis(2-methoxyethyl) Ester;Bis(2-methoxyethyl) Azodicarboxylate;Bis(2-Methoxyethyl) diazene-1,2-dicarboxylate;DMEAD;Di-2-methoxyethyl azodicarboxylate >=96.5% (GC);1,2-Diazenedicarboxylic acid, 1,2-bis(2-methoxyethyl) ester;bis(2-methoxyethyl)(E)-diazene-1,2-dicarboxylate
• CAS NO: 940868-64-4
• Molecular Formula: C8H14N2O6
• Molecular Weight: 234.20656
• Mol File: 940868-64-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 39.9-40.4 °C(Solv: toluene (108-88-3); hexane (110-54-3))
• Boiling Point: 322.9±27.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Di-2-Methoxyethyl azodicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Di-2-Methoxyethyl azodicarboxylate(940868-64-4)
• EPA Substance Registry System: Di-2-Methoxyethyl azodicarboxylate(940868-64-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 940868-64-4(Hazardous Substances Data)

Usage

Description

Di-2-Methoxyethyl azodicarboxylate, with the molecular formula C6H10N2O5, is a chemical compound that serves as a reagent in organic synthesis. It is particularly utilized in the formation of azo compounds and the Mitsunobu reaction, a common method for the inversion of alcohols to their corresponding carbonyl compounds. Di-2-Methoxyethyl azodicarboxylate is recognized for its potent oxidizing properties, which can lead to violent reactions with reducing agents, and it is classified as potentially hazardous and explosive when heated to decomposition.

Uses

Used in Organic Synthesis:
Di-2-Methoxyethyl azodicarboxylate is used as a reagent for the synthesis of azo compounds, which are important in various applications such as dyes, pigments, and biological stains. Its role in the formation of these compounds is crucial due to its ability to facilitate the coupling of diazonium salts with phenols or amines.
Used in the Mitsunobu Reaction:
In the Mitsunobu reaction, Di-2-Methoxyethyl azodicarboxylate is employed as a key component to promote the conversion of alcohols to aldehydes or ketones. This reaction is widely used in the synthesis of complex organic molecules and pharmaceuticals, where the inversion of functional groups is necessary.
Used in Research and Development:
Due to its reactivity and potential for hazardous reactions, Di-2-Methoxyethyl azodicarboxylate is also used in research and development settings to explore new synthetic pathways and understand the mechanisms of oxidation and reduction in organic chemistry.
Safety Precautions:
Given its powerful oxidizing nature and potential for explosive decomposition, Di-2-Methoxyethyl azodicarboxylate must be handled and stored with extreme care. Proper safety measures, including the use of protective equipment and adherence to specific storage conditions, are essential when working with this compound to prevent accidents and ensure the safety of personnel and facilities.

Upstream product

• 940868-65-5 di-2-dimethoxyethyl hydrazinedicarboxylate 

Relevant articles and documents

METHOD FOR PRODUCING AZO COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo groups of hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of vanadium or cerium compounds, and a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Method of manufacturing Azodicarboxylic acid diester compd. (by machine translation)

PROBLEM TO BE SOLVED: To provide a manufacturing method in which an azodicarboxylate diester compound can be efficiently obtained in a high yield and which is industrially advantageous.SOLUTION: There is provided a manufacturing method for azodicarboxylate diester compound including: a process (a) of obtaining a 1,2-hydrazine dicarboxylate diester compound through reaction between hydrazine and a halocarbonate ester; and a process (b) of obtaining an azodicarboxylate diester compound represented by general formula (2) (where A represents a hydrocarbon or a hydrocarbon which may have an ether bond) by oxidizing the 1,2-hydrazine dicarboxylate diester compound obtained in the process (a), the 1,2-hydrazine dicarboxylate diester compound being neither isolated nor refined.

DMEAD: a new dialkyl azodicarboxylate for the Mitsunobu reaction

Di-2-methoxyethyl azodicarboxylate (DMEAD) is prepared in 65% yield in two steps as a crystalline solid. Use of DMEAD in the Mitsunobu reaction of a variety of alcohols with pronucleophiles results in good yields of the products under sufficient stereospecificity of inversion, as conventional diisopropyl azodicarboxylate (DIAD) does. Isolation of the product is, however, much easier with DMEAD than that with DIAD, because the hydrazine produced from DMEAD is highly hydrophilic and is completely separable by a simple extraction into neutral water. Purification of the organic layer, after separation of the other by-product, triphenylphosphane oxide, by filtration, easily provides high purity of the product in a good yield. Concentration of the water layer yields the hydrazine, which can be reused for the preparation of DMEAD. One-step removal of the two by-products by the aqueous extraction was also possible when trimethylphosphane and DMEAD were employed.