11627
Diethyl azodicarboxylate solution
purum, ~40% in toluene (H-NMR)
Synonym(s):
1,2-Ethoxycarbonyl diazene solution, DEAD, Diethoxycarbonyldiazene solution, Diethyl azodiformate solution, NSC 3474, NSC 679015, Unifoam AZ-AE 200
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About This Item
grade
purum
Quality Level
form
solid
concentration
~40% in toluene (H-NMR)
refractive index
n20/D 1.47
functional group
azo
storage temp.
2-8°C
SMILES string
CCOC(=O)\N=N/C(=O)OCC
InChI
1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
InChI key
FAMRKDQNMBBFBR-BQYQJAHWSA-N
Application
DEAD can also be used as a reagent in the:
- Synthesis of esters, ethers, amines, and thioethers of alcohols.
- Oxidation of alcohols to carbonyl derivatives using ZnBr2 as a catalyst via dehydrogenation reaction.
- Conversion of alcohol to an azide key intermediate in the total synthesis of immunostimulant α-galactosylceramides.
- Synthesis of aza-β-lactams from aryl(alkyl)ketenes.
- Synthesis of 1H-1,2,4-triazole-1,4(5H)-dicarboxylate derivatives.
- Diels-Alder type reactions.
- 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
Reagent for:
- Annulation of N-protected imines
- α-thiocyanation of enolizable ketones with ammonium thiocyanate
- Diels-Alder reactions
Other Notes
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Danger
Hazard Classifications
Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
target_organs
Central nervous system, Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
105.8 °F - closed cup
flash_point_c
41 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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