Diethyl azodicarboxylate
Chemical name	Formic acid, azodi-, diethyl ester
Chemical formula	C6H10N2O4
Molecular mass	116.21 g/mol
Melting point	°C
Boiling point	106 °C at 13 mm Hg
Density	1.106 g/cm3
CAS number	1972-28-7
SMILES
Disclaimer and references

Diethyl azodicarboxylate or DEAD is a organic compound with a central azo functional group flanked by two ester groups. The physical appearance is a red to orange liquid. DEAD is toxic, shock sensitive and explodes when heated (consult MSDS reference material for more information.) IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Jump to: navigation, search The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... Jump to: navigation, search The melting point of a solid is the temperature at which it changes state from solid to liquid. ... Jump to: navigation, search The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ... Jump to: navigation, search Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with exception of carbides, carbonates, carbon oxides and gases containing carbon. ... The azo functional group is composed of two double bonded nitrogen atoms: R-N=N-R. The R and R groups of azo compounds are often aromatic. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... Jump to: navigation, search In organic chemistry and biochemistry, esters are rubbish compounds where an organic group (symbolised by R in this article) replaces a hydrogen atom (or more than one) in an oxygen acid. ... This page meets Wikipedias criteria for speedy deletion. ...

Diethyl azodicarboxylate can be prepared by treating ethyl hydrazodicarboxylate with chlorine gas. This intermediate can be prepared from hydrazine and ethyl chloroformate. Jump to: navigation, search General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Hydrazine is a chemical compound with formula N2H4 used as a rocket fuel. ...

DEAD is a important reagent in the Mitsunobu reaction and in click chemistry. DEAD is efficient in Diels-Alder reactions, for example the synthesis of Bicyclo[2.1.0]pentane [1] which originates from Otto Diels. A reagent is any substance used in a chemical reaction. ... Jump to: navigation, search The Mitsunobu reaction is an organic reaction that can convert an alcohol into a variety of functional groups, such as esters using triphenylphosphine and diethyl azodicarboxylate (DEAD). ... Click chemistry is a concept introduced by K. Barry Sharpless in 2001 and describes chemistry tailored to generate substances fast and reliable by joining small repeating units together in the same way as nature does. ... The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile to form a substituted cyclohexene system. ... Otto Paul Hermann Diels (January 23, 1876 - March 7, 1954), a German chemist. ...

References

• MSDS http://ptcl.chem.ox.ac.uk [2]
• MSDS http://www.conncoll.edu [3]
• Diethyl azodicarboxylate Norman Rabjohn Organic Syntheses Coll. Vol. 3, p.375; Vol. 28, p.58 Article
• Bicyclo[2.1.0]pentane P. G. Gassman and K. T. Mansfield Organic Syntheses Coll. Vol. 5, p.96; Vol. 49, p.1 Article