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Diethyl azodicarboxylate

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Diethyl azodicarboxylate Basic information

Product Name:
Diethyl azodicarboxylate
Synonyms:
  • Diazenedicarboxylic acid, diethyl ester
  • Diethoxycarbonyldiazene
  • Diethyl (E)-1,2-diazenedicarboxylate
  • Diethyl diazodicarboxylate
  • dlethylazodicarboxylate
  • Ethyl azodicarboxylate
  • Formic acid, azodi-, diethyl ester
  • DIETHYL AZODIFORMATE
CAS:
1972-28-7
MF:
C6H10N2O4
MW:
174.15
EINECS:
217-821-7
Product Categories:
  • Pharmaceutical intermdiate
  • Aliphatics
  • Aromatic Esters
  • Inhibitors
Mol File:
1972-28-7.mol
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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.
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.
InChIKey
FAMRKDQNMBBFBR-FPLPWBNLSA-N
CAS DataBase Reference
1972-28-7(CAS DataBase Reference)
NIST Chemistry Reference
Diethyl azo diformate(1972-28-7)
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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
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
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Diethyl azodicarboxylate Usage And Synthesis

Chemical Properties

Clear orange to orange-red liquid

Uses

A fluorescent CDK inhibitor for treatment of cancer

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.

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