AZODICARBOXYLIC BISMORPHOLIDE Chemical Properties

Melting point:

141-143 °C

Boiling point:

397.6±52.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-0.97±0.20(Predicted)

Appearance

Light yellow to yellow Solid

BRN 

1013753

InChI

InChI=1S/C10H16N4O4/c15-9(13-1-5-17-6-2-13)11-12-10(16)14-3-7-18-8-4-14/h1-8H2

InChIKey

CHAMTJKQPOMXTI-UHFFFAOYSA-N

SMILES

N(C(N1CCOCC1)=O)=NC(N1CCOCC1)=O

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

AZODICARBOXYLIC BISMORPHOLIDE Usage And Synthesis

Uses

Azodicarboxylic dimorpholide has been used in the galanthamine ring system reaction that utilizes an intramolecular Heck reaction to establish the benzofuran ring system. Galanthamine exhibits potent acetylcholinesterase inhibitory activity and is important in the management of Alzheimer′s disease.

General Description

Azodicarboxylic dimorpholide is a yellow to dark yellow powder or crystals

Synthesis

To a stirred mixture of diethyl azodicarboxylate (40 wt% toluene solution, 5 mL, 11.5 mmol, 1 eq.) and ether (25 mL) was slowly added an ether solution (25 mL) of morpholine (1.98 mL, 23 mmol, 2 eq.) through a dropping funnel at 0 °C, the dropwise addition process continued for 3 hours. The reaction mixture was then continued to stir for 2 hours under slow warming to room temperature. The resulting yellow precipitate was collected by vacuum filtration, washed with cold ether and dried over a filter to afford azodicarbonyl dimorpholine (ADDM) as a yellow-orange solid (1.62 g, 55% yield). The NMR hydrogen spectrum (CDCl3, 400 MHz) data were as follows: δ 3.61 (multiple peaks, 4H, 2 × CH2), 3.74 (multiple peaks, 8H, 4 × CH2), 3.83 (multiple peaks, 4H, 2 × CH2).

References

[1] Tetrahedron Letters, 2013, vol. 54, # 35, p. 4624 - 4628

AZODICARBOXYLIC BISMORPHOLIDE(10465-82-4)Related Product Information

• N,N,N',N'-Tetramethylazodicarboxamide
• Diisopropyl azodicarboxylate
• 1,1'-(Azodicarbonyl)-dipiperidine
• Di-tert-Butyl azodicarboxylate
• Diethyl azodicarboxylate
• Dibenzyl azodicarboxylate
• Morpholinazole
• N-Formylmorpholine
• N-(2-METHOXYETHYL)UREA
• AZODICARBOXYLIC BISMORPHOLIDE
• Azodicarbonamide
• C-MORPHOLIN-4-YL-METHYLAMINE