Wikipedia

1,2-Dimorpholinoethane

1,2-Dimorpholinoethane is an organic chemical and specifically a nitrogen-oxygen heterocyclic compound. At room temperature it is a solid with a melting point of 75 °C.[2] It has two tertiary amines in the same molecule meaning it is ideal for use as a polyurethane catalyst.[3] It has the CAS Registry Number 1723-94-0 and is TSCA and REACH registered and on EINECS with the number 217-026-5.[4] The IUPAC name is 4-(2-morpholin-4-ylethyl)morpholine and the chemical formula C10H20N2O2.[5]

1,2-Dimorpholinoethane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 217-026-5
UNII
  • InChI=1S/C10H20N2O2/c1(11-3-7-13-8-4-11)2-12-5-9-14-10-6-12/h1-10H2
    Key: QRQKCMFVJWNKQI-UHFFFAOYSA-N
  • C1COCCN1CCN2CCOCC2
Properties
C10H20N2O2
Molar mass 200.282 g·mol−1
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H315, H317, H318, H319, H335
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synonyms

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Section reference.[6]

  • 4,4'-Ethylenedimorpholine
  • 4,4'-(Ethane-1,2-diyl)bismorpholine
  • Morpholine, 4,4'-(1,2-ethanediyl)bis-
  • 1,2-Di-N-morpholinylethane
  • Morpholine,4,4'-(1,2-ethanediyl)bis-
  • Morpholine, 4,4'-ethylenedi-

Uses and synthesis

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As the molecule has two tertiary nitrogen atoms in the molecule, the substance finds use as a catalyst for polyurethane[7] including PU foams.[8][9][10][11][12]

1,2-Dimorpholinoethane has been used to make transition metal complexes. As there are two nitrogen atoms in the molecule it acts as a bidentate ligand in these complexes.[13] These complexes have then be used in antibacterial applications.[14]

Toxicity

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The toxicity of the compound and tertiary amines in general has been studied and published.[15]

References

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  1. ^ "1,2-Dimorpholinoethane". pubchem.ncbi.nlm.nih.gov.
  2. ^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2023-06-23.
  3. ^ "1,2-Dimorpholinoethane | C10H20N2O2 | ChemSpider". www.chemspider.com. Retrieved 2023-06-23.
  4. ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2023-06-23.
  5. ^ "4,4'-(ethane-1,2-diyl)bismorpholine CAS#: 1723-94-0". www.chemicalbook.com. Retrieved 2023-06-23.
  6. ^ PubChem. "1,2-Dimorpholinoethane". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-06-23.
  7. ^ Van Maris, Roger; Tamano, Yutaka; Yoshimura, Hiroyuki; Gay, Kenneth M. (July 2005). "Polyurethane Catalysis by Tertiary Amines". Journal of Cellular Plastics. 41 (4): 305–322. doi:10.1177/0021955X05055113. ISSN 0021-955X. S2CID 98546778.
  8. ^ Bacaloglu, R.; Cotarcâ, L.; Marcu, N.; Tölgyi, St (1988). "Kinetics and mechanism of isocyanate reactions. II. Reactions of Aryl Isocyanates with Alcohols in the presence ob tertiary amines". Journal für Praktische Chemie. 330 (4): 530–540. doi:10.1002/prac.19883300406.
  9. ^ Adam, Norbert; Avar, Geza; Blankenheim, Herbert; Friederichs, Wolfgang; Giersig, Manfred; Weigand, Eckehard; Halfmann, Michael; Wittbecker, Friedrich-Wilhelm; Larimer, Donald-Richard; Maier, Udo; Meyer-Ahrens, Sven; Noble, Karl-Ludwig; Wussow, Hans-Georg (2005). "Polyurethanes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_665.pub2. ISBN 978-3-527-30673-2.
  10. ^ "Jeffcat Amine Catalysts for the Polyurethane Industry" (PDF). 2006. Archived from the original (PDF) on 2007-11-29. Retrieved 2007-10-23.
  11. ^ Muuronen, Mikko; Deglmann, Peter; Tomović, Željko (2019-06-21). "Design Principles for Rational Polyurethane Catalyst Development". The Journal of Organic Chemistry. 84 (12): 8202–8209. doi:10.1021/acs.joc.9b01319. ISSN 0022-3263. PMID 31125228. S2CID 164217639.
  12. ^ Marsella, John A. (February 1987). "Homogeneously catalyzed synthesis of .beta.-amino alcohols and vicinal diamines from ethylene glycol and 1,2-propanediol". The Journal of Organic Chemistry. 52 (3): 467–468. doi:10.1021/jo00379a035. ISSN 0022-3263.
  13. ^ Mazhar-Ul-Haque; Sakhawat Hussain, M.; Ahmed, Jamil (1992-02-01). "Tetrahedral complexes of 1,2-dimorpholinoethane and 1,3-dimorpholinopropane: Crystal and molecular structure of dichloro(1,2-dimorpholinoethane)cobalt(II)". Journal of Crystallographic and Spectroscopic Research. 22 (1): 37–41. doi:10.1007/BF01161361. ISSN 1572-8854. S2CID 98169856.
  14. ^ Goudarziafshar, Hamid; Rezaeivala, Majid; Khosravi, Fayezeh; Abbasityula, Yunes; Yousefi, Somaieh; Özbek, Neslihan; Eigner, Václav; Dušek, Michal (2015-01-01). "Synthesis, characterization and crystal structures of new Zinc(II) and Nickel(II) complexes containing morpholine moiety and their antibacterial studies". Journal of the Iranian Chemical Society. 12 (1): 113–119. doi:10.1007/s13738-014-0462-2. ISSN 1735-2428. S2CID 94843521.
  15. ^ Albrecht, William N; Stephenson, Richard L (1988). "Health hazards of tertiary amine catalysts". Scandinavian Journal of Work, Environment & Health. 14 (4): 209–219. doi:10.5271/sjweh.1930. ISSN 0355-3140. JSTOR 40965565. PMID 3051334. S2CID 7451672.
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