4,4'-Oxydianiline

4,4'-Oxydianiline

Names
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	101-80-4
ChEMBL	ChEMBL354663
ChemSpider	7298
Jmol interactive 3D	Image
KEGG	C14759
InChI InChI=1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 Key: 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,13-14H2 Key: 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
NFPA 704	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 [77 °F], 100 kPa).
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Infobox references

4,4’-Oxydianiline 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.^[1]

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:^[2]

References

1. 11th ROC: 4,4'-Oxydianiline
2. 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.

External links

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