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Diethyl azodicarboxylate

Diethyl azodicarboxylate structure

CAS No:
1972-28-7
Formula:
C6H10N2O4
Chemical 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
Categories:
Organic Chemistry > Nitrogen Compounds

Description

Clear orange to orange-red liquid

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

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 Basic Attributes

Molecular Weight：

174.15

Exact Mass：

174.15

BRN：

908662

EC Number：

217-821-7

Color/Form：

Clear, orange

HScode：

29270000

Characteristics

Density：

1.106

Melting Point：

6°C

Boiling Point：

106°C (13 mmHg)

Refractive Index：

n20/D1.47

Critical Temperature & Pressure：

2-8°C

Safety Information

Packing level：

III

Hazard category：

6.1

wgk germany：

hazard class code：

F,Xn,Xi

safety instructions：

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

Hazard Statements：

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

RIDADR：

UN 3233 4.1

GHS Classification：

|Danger|H240 (84.44%): Heating may cause an explosion [Danger Self-reactive substances and mixtures; Organic peroxides]|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, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

DACA OEt

Diethyl azodicarboxylate Use and Manufacturing

A fluorescent CDK inhibitor for treatment of cancer

Reactant for preparation of:Immunostimulants α-GalactosylceramidesCellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulasesBisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferaseDerivatives of F200 and S383 with cannabinoid CB1 receptor binding activitiesAza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenesReagent for:Annulation of N-protected iminesα-thiocyanation of enolizable ketones with ammonium thiocyanateDiels-Alder reactions

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