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563110

Diethyl azodicarboxylate solution

40 wt. % in toluene

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

Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
1972-28-7
Molecular Weight:
174.15
PubChem Substance ID:
24880080
UNSPSC Code:
12352108
Beilstein/REAXYS Number:
908662
MDL number:
MFCD00009103

concentration

40 wt. % in toluene

refractive index

n20/D 1.4690

bp

116-117 °C

density

0.956 g/mL at 25 °C

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

General description

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

Application

A commonly used activating reagent in Mitsunobo reactions.[1]
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

Packaging

100g unit contains ca. 40g DEAD solute
25g unit contains ca. 10g DEAD solute

Disclaimer

Toxic, Irritant, Flammable

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This Item
135992225541258822
Diethyl azodicarboxylate solution 40 wt. % in toluene

Sigma-Aldrich

563110

Diethyl azodicarboxylate solution

Di-tert-butyl azodicarboxylate 98%

Sigma-Aldrich

135992

Di-tert-butyl azodicarboxylate

Diisopropyl azodicarboxylate 98%

Sigma-Aldrich

225541

Diisopropyl azodicarboxylate

4-Methylmorpholine N-oxide solution 50 wt. % in H2O

Sigma-Aldrich

258822

4-Methylmorpholine N-oxide solution

density

0.956 g/mL at 25 °C

density

-

density

1.027 g/mL at 25 °C (lit.)

density

1.13 g/mL at 25 °C

refractive index

n20/D 1.4690

refractive index

-

refractive index

n20/D 1.420 (lit.)

refractive index

n20/D 1.4201

bp

116-117 °C

bp

-

bp

75 °C/0.25 mmHg (lit.)

bp

118.5 °C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

functional group

azo

functional group

azo

functional group

azo

functional group

ether

concentration

40 wt. % in toluene

concentration

-

concentration

-

concentration

50 wt. % in H2O

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Danger

target_organs

Central nervous system, Respiratory system

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

flash_point_f

105.8 °F - closed cup

flash_point_c

41 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hazard Classifications

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM8638
MKCL0488
MKCJ1314
MKCF3967
MKCC6724

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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
Jetze Visser et al.
Nature communications, 6, 6933-6933 (2015-04-29)
Despite intensive research, hydrogels currently available for tissue repair in the musculoskeletal system are unable to meet the mechanical, as well as the biological, requirements for successful outcomes. Here we reinforce soft hydrogels with highly organized, high-porosity microfibre networks that
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
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Global Trade Item Number

SKUGTIN
563110-100G04061832583792
563110-25G04061832583808

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