Diisopropyl azodicarboxylate

Structural formula
General
Surname	Diisopropyl azodicarboxylate
other names	Diisopropyl azodicarboxylate; DIAD;
Molecular formula	C 8 H 14 N 2 O 4
Brief description	reddish, pungent smelling liquid
External identifiers / databases
EC number	219-502-8
ECHA InfoCard	100.017.730
PubChem	5363146
Wikidata	Q411418
properties
Molar mass	202.21 g mol −1
Physical state	liquid
density	1.03 g cm −3
Melting point	3-5 ° C
boiling point	75 ° C (0.4 h Pa )
Vapor pressure	1.04 h Pa (at 20 ° C)
solubility	almost insoluble in water
safety instructions
H and P phrases	H: 315-319-335-351-373-411
	P: 261-273-281-305 + 351 + 338
Toxicological data	2150 mg kg −1 ( LD 50 , rabbit , transdermal )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diisopropyl azodicarboxylate is a reagent for the Mitsunobu reaction . The compound can be used as an alternative to the explosive compound azodicarboxylic acid diethyl ester .

Manufacturing

The preparation can take place analogously via the synthetic routes to the diethyl azodicarboxylate , the corresponding compounds containing the isopropyl group being used instead of the ethyl group-substituted starting materials.

Chemical properties, safety

Compared to diethyl azodicarboxylate, DIAD is much less thermally unstable. The connection is not explosive in terms of the Explosives Act . The steel sleeve test shows an explosion with a nozzle diameter of no more than 1 mm. There is no propagation of detonation in the BAM-2 "tube test. The connection is not sensitive to shock . The use of the substance under thermal stress is still not safe. The decomposition proceeds in the sense of thermal runaways with a considerable release of heat. A purification by distillation of the Compound should only be considered after a corresponding safety analysis, taking into account the decomposition behavior.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet diisopropylazodicarboxylate (PDF) from Merck , accessed on February 9, 2019.
↑ ^a ^b ^c ^d Safety data sheet from Dynamit Nobel , as of January 16, 2004.
↑ patent; Wallace and Tiernan; NL 6408826; 1963; Chem. Abstr .; English; 63; Pp. 6865-6866; 1965.
↑ ^a ^b Data sheet diisopropyl azodicarboxylate from Sigma-Aldrich , accessed on February 9, 2019 ( PDF ).

[merck-1] ↑ ^a ^b ^c ^d ^e data sheet diisopropylazodicarboxylate (PDF) from Merck , accessed on February 9, 2019.

[Dynamit_Nobel-2] Safety data sheet from Dynamit Nobel , as of January 16, 2004.

[3] tent; Wallace and Tiernan; NL 6408826; 1963; Chem. Abstr .; English; 63; Pp. 6865-6866; 1965.

[Sigma-4] Data sheet diisopropyl azodicarboxylate from Sigma-Aldrich , accessed on February 9, 2019 ( PDF ).