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2-Morpholinoethyl isocyanide (CAS 78375-48-1)

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Alternate Names:
MEI; 4-(2-Isocyanoethyl)morpholine
CAS Number:
78375-48-1
Purity:
≥98%
Molecular Weight:
140.18
Molecular Formula:
C7H12N2O
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Morpholinoethyl isocyanide is a compound of interest in synthetic organic chemistry, particularly in the context of isocyanide-based multicomponent reactions (MCRs). Its morpholino ring provides both steric bulk and an electron-donating effect, which can influence the reactivity and selectivity of the isocyanide group in these reactions. Researchers explore its use in the Ugi reaction, where it can be combined with aldehydes, amines, and carboxylic acids to synthesize a diverse array of products including peptidomimetics, heterocycles, and other complex organic molecules. The morpholino moiety is also recognized for its potential to impart solubility in polar solvents, which is advantageous during reaction optimization and product isolation. Studies involving 2-Morpholinoethyl isocyanide aim to uncover new catalytic systems and reaction conditions that can enhance the efficiency and scope of MCRs. In addition, this compound′s utility in constructing pharmacophore models is examined, as the products derived from such isocyanides can resemble biologically active structures and thus are relevant for the synthesis of small-molecule libraries for high-throughput screening.


2-Morpholinoethyl isocyanide (CAS 78375-48-1) References

  1. Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones.  |  Liang, HW., et al. 2018. Angew Chem Int Ed Engl. 57: 5720-5724. PMID: 29601660
  2. Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins.  |  Vroemans, R., et al. 2018. Beilstein J Org Chem. 14: 626-633. PMID: 29623124
  3. IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine.  |  Ambule, MD., et al. 2019. Chem Commun (Camb). 55: 10872-10875. PMID: 31433406
  4. Metal-free aminofluorination of α-diazo 2H-benzopyran-4-one: convenient access to β-fluoramides.  |  Zhang, W., et al. 2022. Org Biomol Chem. 20: 7027-7030. PMID: 36017814
  5. A practical isocyanide-based multicomponent synthesis of polysubstituted cyclopentenes  |  A Sağırli, Y Dürüst, B Kariuki, DW Knight - Tetrahedron, 2013 - Elsevier. January 2013,. Tetrahedron. Volume 69, Issue 1, 7: Pages 69-72.
  6. Versatile side chain modification via isocyanide-based multicomponent reactions: tuning the LCST of poly(2-oxazoline)s†  |  Ansgar Sehlinger,a Bart Verbraeken,b Michael A. R. Meier*a and Richard Hoogenboom*b. 2015,. Polym. Chem.,. 6,: 3828-3836.
  7. Ugi multicomponent reaction to prepare peptide–peptoid hybrid structures with diverse chemical functionalities†  |  Manuel Hartweg a, Charlotte J. C. Edwards-Gayle bc, Elham Radvar a, Dominic Collis a, Mehedi Reza d, Michael Kaupp efg, Jan Steinkoenig ORCID logoefg, Janne Ruokolainen d, Robert Rambo c, Christopher Barner-Kowollik ORCID logoefg, Ian W. Hamley ORCID logob, Helena S. Azevedo ORCID logoa and C. Remzi Becer ORCID logo*a. 2018,. Polym. Chem.,. 9,: 482-489.
  8. A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles  |  https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201700619. November 10, 2017. Advanced Synthesis & Catalysis. Volume359, Issue21: Pages 3826-3830.
  9. Synthesis of [1,2,4,5]tetrazino[6′,1′:2,3]imidazo[4,5-c]isoquinolin-5-ones by microwave-assisted three-component reaction  |  L Pellegatti, E Vedrenne, MA Hiebel, F Buron… - Tetrahedron letters, 2011 - Elsevier. 12 October 2011,. Tetrahedron Letters. Volume 52, Issue 41,: Pages 5224-5228.
  10. Microwave-assisted solid-phase Ugi four-component condensations  |  AML Hoel, J Nielsen - Tetrahedron letters, 1999 - Elsevier. 14 May 1999,. Tetrahedron Letters. Volume 40, Issue 20,: Pages 3941-3944.
  11. A DFT study on the reaction mechanisms of isocyanide-based multicomponent synthesis of polysubstituted cyclopentenes  |  Y Wang, D Wei, Y Zhu, P Liu, M Tang - Computational and Theoretical …, 2013 - Elsevier. 15 August 2013,. Computational and Theoretical Chemistry. Volume 1018,: Pages 85-90.
  12. Bromodimethylsulfonium bromide (BDMS) catalyzed synthesis of imidazo[1,2-a]pyridine derivatives and their fluorescence properties  |  AT Khan, RS Basha, M Lal - Tetrahedron Letters, 2012 - Elsevier. 25 April 2012,. Tetrahedron Letters. Volume 53, Issue 17,: Pages 2211-2217.
  13. Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of strong CH-acids: one-pot synthesis of highly functionalized annulated 4H-pyrans  |  MB Teimouri, R Bazhrang, V Eslamimanesh, A Nouri - Tetrahedron, 2006 - Elsevier. 27 March 2006,. Tetrahedron. Volume 62, Issue 13,: Pages 3016-3020.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Morpholinoethyl isocyanide, 10 ml

sc-251788
10 ml
$158.00