563110

Sigma-Aldrich

Diethyl azodicarboxylate solution

40 wt. % in toluene

Synonym(s):
NSC 679015, Diethoxycarbonyldiazene solution, NSC 3474, DEAD, Unifoam AZ-AE 200, Diethyl azodiformate solution, 1,2-Ethoxycarbonyl diazene solution
Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
Molecular Weight:
174.15
Beilstein/REAXYS Number:
908662
MDL number:
PubChem Substance ID:

Quality Level

concentration

40 wt. % in toluene

refractive index

n20/D 1.4690

bp

116-117 °C

density

0.956 g/mL at 25 °C

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

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General description

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

Application

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
A commonly used activating reagent in Mitsunobo reactions.

Packaging

25, 100 g in glass bottle
100g unit contains ca. 40g DEAD solute
25g unit contains ca. 10g DEAD solute

Warning

Toxic, Irritant, Flammable

Signal Word

Danger

hazcat

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Self-react. C - Skin Irrit. 2 - STOT RE 2

Target Organs

Central nervous system

storage_class_code

4.1A - Other explosive hazardous materials

WGK Germany

WGK 3

Flash Point(F)

105.8 °F - closed cup

Flash Point(C)

41 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

A Fürstner et al.
The Journal of organic chemistry, 65(6), 1738-1742 (2000-04-06)
A concise synthesis of the hexahydroazepine moiety 13 of (-)-balanol 1 is described that comprises only eight steps and is distinctly shorter than all previous reported approaches to this particular compound. Sharpless epoxidation of divinylcarbinol 4 and ring closing alkene...
Gregory S Watson et al.
Acta biomaterialia, 21, 109-122 (2015-03-17)
Geckos, and specifically their feet, have attracted significant attention in recent times with the focus centred around their remarkable adhesional properties. Little attention however has been dedicated to the other remaining regions of the lizard body. In this paper we...
Adrian Egli et al.
The Journal of infectious diseases, 210(5), 717-727 (2014-03-13)
Feedback mechanisms between interferons α and λ (IFNs) may be affected by single nucleotide polymorphisms (SNP) in interleukin 28B (IL-28B; IFN-λ3) promoter region and may influence cytomegalovirus (CMV) replication. We associated IL-28B SNPs with the risk of CMV replication after...
Fany Reffuveille et al.
Antimicrobial agents and chemotherapy, 58(9), 5363-5371 (2014-07-02)
Biofilm-related infections account for at least 65% of all human infections, but there are no available antimicrobials that specifically target biofilms. Their elimination by available treatments is inefficient since biofilm cells are between 10- and 1,000-fold more resistant to conventional...
Victor Y L Leung et al.
Stem cells (Dayton, Ohio), 32(8), 2164-2177 (2014-04-17)
Intervertebral disc degeneration is associated with back pain and radiculopathy which, being a leading cause of disability, seriously affects the quality of life and presents a hefty burden to society. There is no effective intervention for the disease and the...

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