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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34384;
ChEMBL	ChEMBL354663 ;
ChemSpider	7298 ;
ECHA InfoCard	100.002.707
EC Number	202-977-0;
KEGG	C14759 ;
PubChem CID	7579;
UNII	28DLB4Z70T ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID0021094 ;
	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
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H331, H340, H350, H361f, H411
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+310, P302+352, P304+340, P308+313, P311, P312, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
NFPA 704 (fire diamond)	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

"11th ROC: 4,4'-Oxydianiline" (PDF). Archived (PDF) from the original on 2009-01-31. Retrieved 2008-02-28.
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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[1] "11th ROC: 4,4'-Oxydianiline" (PDF). Archived (PDF) from the original on 2009-01-31. Retrieved 2008-02-28.

[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. ISBN 3527306730.