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4,4'-Oxydianiline

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4,4′-Oxydianiline
Names
Preferred IUPAC name 4,4′-Oxydianiline
Other names 4,4′-Diaminodiphenyl ether; 4-Aminophenyl ether; 4,4′-Oxybisbenzenamine; Bis(4-aminophenyl) ether; 4,4′-ODA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.707 Edit this at Wikidata
EC Number
  • 202-977-0
KEGG
PubChem CID
UNII
UN number 3077
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2Key: HLBLWEWZXPIGSM-UHFFFAOYSA-N
  • InChI=1/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2Key: HLBLWEWZXPIGSM-UHFFFAOYAM
SMILES
  • O(c1ccc(N)cc1)c2ccc(cc2)N
Properties
Chemical formula C12H12N2O
Molar mass 200.24 g/mol
Appearance Colorless crystalline solid
Melting point 188 to 192 °C (370 to 378 °F; 461 to 465 K)
Boiling point 219 °C (426 °F; 492 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H311, H331, H340, H350, H361f, H411
Precautionary statements P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
2
Flash point 219 °C (426 °F; 492 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4,4′-Oxydianiline (ODA) is an organic compound with the formula O(C6H4NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and cross-linking agent for polymers, especially the polyimides, such as Kapton.

Uses

4,4′-Oxydianiline is used in the production of a wide variety of polymer resins. The primary use lies in the production of polyimide and poly(ester)imide resins. These resins are used for their temperature-resistant properties and are utilized in products including wire enamels, coatings, film, adhesives, insulating varnishes, coated fabrics, flame-retardant fibers, oil sealants and retainers, insulation for cables and printed circuits, and laminates and composite for aerospace vehicles.

Other applications of 4,4′-oxydianiline include the production of poly(amide)imide resins (which are used in the manufacture of heat-resistant wire enamels and coatings), as an intermediate in the manufacture of epoxy resins and adhesives, and in the production of aromatic polyether imides. Its use in the production of polyimine vitrimers has also been proposed.

A specific reaction involving industrial use of 4,4′-oxydianiline is in the production of thermostable poly(amideurea) acids, which can be prepared from 4,4′-oxydianiline, pyromellitic dianhydride, and diisocyanates. These poly(amideurea) acids can be used as intermediates in the syntheses of poly(imideurea)s:

Related compounds

References

  1. "11th ROC: 4,4'-Oxydianiline" (PDF). Archived (PDF) from the original on 2009-01-31. Retrieved 2008-02-28.
  2. Schoustra, Sybren K.; Dijksman, Joshua A.; Zuilhof, Han; Smulders, Maarten M. J. (2021). "Molecular control over vitrimer-like mechanics – tuneable dynamic motifs based on the Hammett equation in polyimine materials". Chemical Science. 12 (1): 293–302. doi:10.1039/d0sc05458e. ISSN 2041-6520. PMC 8178953. PMID 34163597.
  3. Chiria, C.I; Tanasã, F. (2000). "Polyureas". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. doi:10.1002/14356007.d21_d01. ISBN 3527306730.

External links

  • MSDS Material Safety Data Sheet provided by Sigma-Aldrich.
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