Diethyl azodicarboxylate

Diethyl azodicarboxylate
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Diethyl diazenedicarboxylate
Systematic IUPAC name
Ethyl N-ethoxycarbonyliminocarbamate
Other names
  • DEAD
  • DEADCAT
  • Diethyl azodiformate
  • Diazenedicarboxylic acid, diethyl ester[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.202 Edit this at Wikidata
EC Number
  • 217-821-7
UNII
  • InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+ checkY
    Key: FAMRKDQNMBBFBR-BQYQJAHWSA-N checkY
  • InChI=1/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
    Key: FAMRKDQNMBBFBR-BQYQJAHWBW
  • O=C(/N=N/C(=O)OCC)OCC
Properties
C6H10N2O4
Molar mass 174.156 g·mol−1
Appearance Orange to red to orange liquid[2]
Density 1.11 g/cm3[3]
Melting point 6 °C (43 °F; 279 K)[4]
Boiling point 104.5 °C (220.1 °F; 377.6 K) at 12 mm Hg[3]
1.420 (20 °C)[3]
Hazards
GHS labelling:
GHS01: ExplosiveGHS07: Exclamation mark
Danger
H240, H302, H312, H315, H319, H332, H335
P210, P220, P234, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P370+P380+P375, P403+P233, P403+P235, P405, P411, P420, P501
Flash point 85 °C (185 °F; 358 K)[5]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT,[6][7] is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.

DEAD is an aza-dienophile and an efficient dehydrogenating agent, converting alcohols to aldehydes, thiols to disulfides and hydrazo groups to azo groups; it is also a good electron acceptor. While DEAD is used in numerous chemical reactions it is mostly known as a key component of the Mitsunobu reaction, a common strategy for the preparation of an amine, azide, ether, thioether, or ester from the corresponding alcohol.[8] It is used in the synthesis of various natural products and pharmaceuticals such as zidovudine, an AIDS drug; FdUMP, a potent antitumor agent; and procarbazine, a chemotherapy drug.

  1. ^ Diethyl azodiformate. Webbook.nist.gov (1972-07-28). Retrieved on 2011-03-15.
  2. ^ Cite error: The named reference msds was invoked but never defined (see the help page).
  3. ^ a b c Cite error: The named reference b1 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference s1 was invoked but never defined (see the help page).
  5. ^ L19348 Diethyl azodicarboxylate, 97% – Alfa Aesar – A Johnson Matthey Company. Alfa.com (1972-07-28). Retrieved on 2011-03-15.
  6. ^ Caroline Cooper (23 July 2010). Organic Chemist's Desk Reference. CRC Press. pp. 109–. ISBN 978-1-4398-1164-1. Retrieved 12 March 2011.
  7. ^ DEAD is sometimes used for another chemical, diethyl acetylenedicarboxylate. P. N. Preston (1980). Benzimidazoles and congeneric tricyclic compounds. John Wiley and Sons. pp. 475–. ISBN 978-0-471-08189-0. Retrieved 12 March 2011.
  8. ^ Barbara., Czakó (2009). Strategic applications of named reactions in organic synthesis: background and detailed mechanisms ; 250 named reactions. Elsevier. ISBN 978-0-12-369483-6. OCLC 634820219.