10340. Diethyl Azodicarboxylate

Nomenclature

CAS number: 1972-28-7; 4143-61-7 ((E)-form) ; 4143-60-6 ((Z)-form)
1,2-Diazenedicarboxylic acid 1,2-diethyl ester; azodiformic acid diethyl ester; diethyl azodiformate; ethyl azodicarboxylate; DEAD.
C6H10N2O4; mol wt 174.15.
C 41.38%, H 5.79%, N 16.09%, O 36.75%.

Description and references

Reagent utilized in the Mitsunobu reaction; also applied in other synthetic transformations. Prepn: T. Curtius, K. Heidenreich, Ber. 27, 773 (1894); N. Rabjohn, Org. Synth. coll. vol. III, 375 (1955); J. C. Kauer, ibid. coll. vol. IV, 411 (1963). Synthetic applications: O. Mitsunobu, M. Yamada, Bull. Chem. Soc. Jpn. 40, 2380 (1967) DOI; F. Yoneda et al., J. Org. Chem. 32, 727 (1967) DOI; A. Shah, M. V. George, Tetrahedron 27, 1291 (1971) DOI; E. E. Smissman, A. Makriyannis, J. Org. Chem. 38, 1652 (1973) DOI PubMed. Reviews: E. J. Stoner in Encyclopedia of Reagents for Organic Synthesis vol. 3, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 1790-1793; S. K. Nune, Synlett 2003, 1221-1222 DOI; A. E. Kümmerle, ibid. 2008, 2723-2724 DOI.

Chemical structure

Properties

Orange liquid. bp15 107-111°; bp13 106°; bp12 104.5°; bp5 93-95°. fp 6°. d420 1.1129; d444.7 1.0876; d461.4 1.0703; d485.9 1.0450. nD20 1.42176. Surface tension (dynes/cm): 33.05 at 22.1°; 31.02 at 42.1°. Explosive. Irritant. Protect from light and heat. Flash pt, closed cup: 235°F (113°C). Sol in dichloromethane, ether, toluene. Decomposes vigorously above 100°.

Caution

Irritating to eyes, skin, and respiratory system.

Use

Reagent in synthetic organic chemistry.