| Identification | Back Directory | [Name]
AZODICARBOXYLIC BISMORPHOLIDE | [CAS]
10465-82-4 | [Synonyms]
NSC 356022
AZODICARBOXYLIC DIMORPHOLIDE
AZODICARBOXYLIC BISMORPHOLIDE
4,4'-Azodicarbonylbis(morpholine)
Diazene-1,2-diylbis(morpholinomethanone)
Azodicarboxylic dimorpholide >=98.0% (N)
Methanone,1,1'-(1,2-diazenediyl)bis[1-(4-morpholinyl)- | [EINECS(EC#)]
418-690-0 | [Molecular Formula]
C10H16N4O4 | [MDL Number]
MFCD00043006 | [MOL File]
10465-82-4.mol | [Molecular Weight]
256.26 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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