Diethyl azodicarboxylate solution

Name: Diethyl azodicarboxylate solution
Brand: ALDRICH

purum, ~40% in toluene (H-NMR)

Synonyme(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

Formule linéaire :

C₂H₅OCON=NCOOC₂H₅

Numéro CAS:

1972-28-7

Poids moléculaire :

174.15

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

57646942

MDL number:

MFCD00009103

Beilstein/REAXYS Number:

908662

Nom du produit

Diethyl azodicarboxylate solution, purum, ~40% in toluene (H-NMR)

InChI

1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+

SMILES string

CCOC(=O)\N=N/C(=O)OCC

InChI key

FAMRKDQNMBBFBR-BQYQJAHWSA-N

grade

purum

form

solid

concentration

~40% in toluene (H-NMR)

refractive index

n20/D 1.47

functional group

azo

storage temp.

2-8°C

Quality Level

100

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Application

Diethyl azodicarboxylate (DEAD) is a reagent used in the Mitsunobu reaction.
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.

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

Reagent for:

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

Other Notes

Reagent used in the Mitsunobu reaction, reviews

pictograms

GHS02,GHS08,GHS07

signalword

Danger

hcodes

H226,H304,H315,H319,H335,H336,H361d,H373,H412

pcodes

P210 - P273 - P301 + P310 - P303 + P361 + P353 - P305 + P351 + P338 - P331

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

Synthesis and thermolysis of Diels-Alder adducts of 2, 9-dialkylpentacenes with diethyl azodicarboxylate

Okamoto K, et al.

Journal of Physical Organic Chemistry, 21(3), 257-262 (2008)

The Mitsunobu reaction: origin, mechanism, improvements, and applications

But TYS and TPH

Chemistry - An Asian Journal, 2(11), 1340-1355 (2007)

Enantioselective synthesis of aza-β-lactams via NHC-catalyzed [2+ 2] cycloaddition of ketenes with diazenedicarboxylates

Huang X-L, et al.

The Journal of Organic Chemistry, 74(19), 7585-7587 (2009)

Oxime-based linker libraries as a general approach for the rapid generation and screening of multidentate inhibitors

Bahta M, et al.

Nature Protocols, 7(4), 686-686 (2012)

The Mitsunobu reaction in the 21st century

Fletcher, S

Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 2(6), 739-752 (2015)

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