503-28-6

Basic information

• Product Name: azomethane
• Synonyms: 1,2-Dimethyldiazene;Azodimethane;Dimethyldiazene;Diazene, dimethyl-
• CAS NO: 503-28-6
• Molecular Formula: C2H6N2
• Molecular Weight: 58.08
• Mol File: 503-28-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: -77.9°C
• Boiling Point: 1.55°C
• Flash Point: °C
• Appearance: /
• Density: 0.5841 (rough estimate)
• Vapor Pressure: 1720mmHg at 25°C
• Refractive Index: 1.4180 (estimate)
• CAS DataBase Reference: azomethane(CAS DataBase Reference)
• NIST Chemistry Reference: azomethane(503-28-6)
• EPA Substance Registry System: azomethane(503-28-6)

Safety Data

• Hazardous Substances Data: 503-28-6(Hazardous Substances Data)

Usage

Safety Profile

A heat-sensitive explosive. Whenheated to decomposition it emits toxic fumes of NOx.

Purification Methods

Purify azomethane by distillation in a vacuum line and store it in the dark at -80o. It is soluble in EtOH, Et2O and EtOAc. It can be EXPLOSIVE. [Beilstein 4 H 562, 4 I 566, 4 II 966, 4 III 1747, 4 IV 3366.]

InChI:InChI=1/C2H6N2/c1-3-4-2/h1-2H3/b4-3+

Upstream product

• 306-37-6 N,N'-Dimethylhydrazine dihydrochloride 
• 4143-41-3 trans-dimethyl-diazene 
• 540-73-8 1,2-Dimethylhydrazine 
• 7782-77-6 cis-nitrous acid 
• 7553-56-2 iodine 
• 119-61-9 benzophenone 
• 57-14-7 N,N-Dimethylhydrazine 
• 286-28-2 cyclohexene sulfide 
• 39245-63-1 cis-2-methyl-3-phenyloxaziridine 
• 52147-56-5 3,4-Dimethyl-1-thia-3,4-diazolidine-2,5-dione 
• 15857-20-2 N,N'-diformyl-N,N'-dimethyl-hydrazine 

Downstream Products

• 4143-42-4 (Z)-azomethane 

Relevant articles and documents

Light-enabled metal-free pinacol coupling by hydrazine

Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.

A Convenient Phase-Transfer Method for Preparation of Pure cis-Dimethyldiazene (cis-Azomethane) in Aqueous Solution. Proton and Carbon NMR Studies of trans- and cis-Dimethyldiazene

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1-Thia-3,4-diazolidine-2,5-dione Functionality: A Photochemical Synthon for the Azo Group

The 1-thia-3,4-diazolidine-2,5-dione functional group was shown to yield azo compounds upon photolysis.This photoreaction when combined with the known ability of this group to react in a Diels-Alder fashion or as a dinucleophile toward alkylating agents greatly increases the utility of this functionality.The dual reactivity of this group was demonstrated in the synthesis of a number of 3,4-dialkyl-1-thia-3,4-diazolodone-2,5-diones.The photolysis of these compounds produced either thermally stable cyclic azo compounds or the decomposition products of thermally unstable azo compounds.