Diethyl azodicarboxylate Chemical Properties

Melting point:

6°C

Boiling point:

106°C (13 mmHg)

Density 

1.106

refractive index 

n20/D 1.47

Flash point:

85°C

storage temp. 

2-8°C

solubility 

Miscible with dichloromethane, diethyl ether and toluene.

form 

liquid

color 

Clear, orange

Sensitive 

Air Sensitive

BRN 

908662

Stability:

Stable, but may explode if heated under confinement. May be shock sensitive. Decomposes vigorously if heated above 100 C. Incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents. Light sensitive.

InChI

InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3

InChIKey

FAMRKDQNMBBFBR-FPLPWBNLSA-N

SMILES

N(C(OCC)=O)=NC(OCC)=O

CAS DataBase Reference

1972-28-7(CAS DataBase Reference)

NIST Chemistry Reference

Diethyl azo diformate(1972-28-7)

Safety Information

Hazard Codes 

F,Xn,Xi

Risk Statements 

5-11-20-36/37/38-48/20-63-65-67-48/20/22-40-20/22-20/21/22-10

Safety Statements 

26-36/37-62-47-36-35

RIDADR 

UN 3233 4.1

WGK Germany 

3

F 

9

Hazard Note 

Toxic/Irritant/Flammable

HazardClass 

6.1

PackingGroup 

III

HS Code 

29270000

MSDS

• Language:English Provider:DEAD
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diethyl azodicarboxylate Usage And Synthesis

Chemical Properties

Clear orange to orange-red liquid

Uses

A fluorescent CDK inhibitor for treatment of cancer

Uses

Reactant for preparation of:

• Immunostimulants α-Galactosylceramides
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes

• Annulation of N-protected imines
• α-thiocyanation of enolizable ketones with ammonium thiocyanate
• Diels-Alder reactions

General Description

DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.

Purification Methods

Dissolve DEAD in toluene, wash it with 10% NaHCO3 till neutral (may require several washes if too much hydrolysis had occurred: check IR for OH bands), then wash with H2O (2x), dry over Na2SO4, filter, evaporate the toluene and distil it through a short Vigreux column (p 11) at as high a vacuum as possible. The main portion boils at 107-111o/15mm. Since it is likely to explode, use an oil bath for heating the still and all operations should be carried -out behind an adequate shield. [Rabjohn Org Synth Coll Vol III 375 1955, see Kauer Org Synth Coll Vol IV 412 1963]. [Beilstein 3 III 233.] It is commercially available as a 40% solution in toluene. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate above and DIAD below]. § A polystyrene supported DEAD version is commercially available with a loading of ~1.2mmol/g.

Diethyl azodicarboxylate(1972-28-7)Related Product Information

• BUTYL OLEATE
• Diethyl phthalate
• Diisopropyl azodicarboxylate
• Ethyl formate
• Diethyl malonate
• Dimethyl 2,2'-azobis(2-methylpropionate)
• Triethyl orthoformate
• Di-tert-Butyl azodicarboxylate
• Urethane
• Methyl acrylate
• Dimethyl succinate
• Bis(4-chlorobenzyl) azodicarboxylate
• Dibenzyl azodicarboxylate
• Tris(trimethylsilyl)phosphate
• 1,1'-(Azodicarbonyl)-dipiperidine
• PIPERAZINE DIHYDROCHLORIDE
• N,N,N',N'-Tetramethylazodicarboxamide
• AZODICARBOXYLIC BISMORPHOLIDE