9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
Names
	Other names 3,4:5,6-Dibenzo-2H-1,2-oxaphosphorin-2-oxide
Identifiers
CAS Number	35948-25-5;
3D model (JSmol)	Interactive image;
ChemSpider	10613171; 9,10-Dihydro-9-oxa-10-phosphaphenanthrene: 11408428;
EC Number	252-813-7;
PubChem CID	6328250; 9,10-Dihydro-9-oxa-10-phosphaphenanthrene: 20504138;
UNII	63LTW1C2TR;
	InChI InChI=1S/C12H9O2P/c13-15-12-8-4-2-6-10(12)9-5-1-3-7-11(9)14-15/h1-8,15H Key: VBQRUYIOTHNGOP-UHFFFAOYSA-N; 9,10-Dihydro-9-oxa-10-phosphaphenanthrene: InChI=1S/C12H9OP/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)14-13-11/h1-8,14H Key: HDXGUOZQUVDYMC-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C3=CC=CC=C3P(=O)O2;
Properties
Chemical formula	C12H9O2P
Molar mass	216.176 g·mol−1
Appearance	white solid
Melting point	119–121 °C (246–250 °F; 392–394 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) is an organophosphorus compound that is used to produce fire retardants. From the chemistry perspective, it is a derivative of hypophosphorous acid as well as a derivative of phenanthrene. The reactivity of the P-H center allows for the conjugation of DOPO to many monomers. Such monomers are incorporated into polymers, conferring fire retardant properties.^[1] It is mainly used for nylon and polyesters,^[2] as well as epoxides.^[3]

The compound is prepared from 2-phenylphenol, which condenses with one equivalent of phosphorus trichloride. Heating that species in the presence of aluminium trichloride results in cyclization. The procedure is completed by hydrolysis.^[4]^[5]

References

^ Qian, Xiaodong; Song, Lei; Jiang, Saihua; Tang, Gang; Xing, Weiyi; Wang, Bibo; Hu, Yuan; Yuen, Richard K. K. (2013). "Novel Flame Retardants Containing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and Unsaturated Bonds: Synthesis, Characterization, and Application in the Flame Retardancy of Epoxy Acrylates". Industrial & Engineering Chemistry Research. 52 (22): 7307–7315. doi:10.1021/ie400872q.
^ Levchik, Sergei V.; Weil, Edward D. (2006). "A Review of Recent Progress in Phosphorus-based Flame Retardants". Journal of Fire Sciences. 24 (5): 345–364. doi:10.1177/0734904106068426.
^ Beard, Adrian; Battenberg, Christian; Sutker, Burton J. (2021). "Flame Retardants". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_123.pub2. ISBN 978-3-527-30385-4. S2CID 261178139.
^ Salmeia, Khalifah A.; Gaan, Sabyasachi (2015). "An overview of some recent advances in DOPO-derivatives: Chemistry and Flame Retardant Applications". Polymer Degradation and Stability. 113: 119–134. doi:10.1016/j.polymdegradstab.2014.12.014.
^ Chernyshev, E. A.; Aksenov, V. I.; Ponomarev, V. V.; Golubtsov, S. A.; Bugerenko, E. F. (1972). "Synthesis and reactions of 10-chloro-9,10-dihydro-10-phospha-9-oxaphenanthrene [6-chloro-6H-dibenz[c,1][1,2]oxaphosphorin]". Zhurnal Obshchei Khimii. 42: 93-6.

[1] Qian, Xiaodong; Song, Lei; Jiang, Saihua; Tang, Gang; Xing, Weiyi; Wang, Bibo; Hu, Yuan; Yuen, Richard K. K. (2013). "Novel Flame Retardants Containing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and Unsaturated Bonds: Synthesis, Characterization, and Application in the Flame Retardancy of Epoxy Acrylates". Industrial & Engineering Chemistry Research. 52 (22): 7307–7315. doi:10.1021/ie400872q.

[2] Levchik, Sergei V.; Weil, Edward D. (2006). "A Review of Recent Progress in Phosphorus-based Flame Retardants". Journal of Fire Sciences. 24 (5): 345–364. doi:10.1177/0734904106068426.

[Ullmanns2021-3] Beard, Adrian; Battenberg, Christian; Sutker, Burton J. (2021). "Flame Retardants". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_123.pub2. ISBN 978-3-527-30385-4. S2CID 261178139.

[4] Salmeia, Khalifah A.; Gaan, Sabyasachi (2015). "An overview of some recent advances in DOPO-derivatives: Chemistry and Flame Retardant Applications". Polymer Degradation and Stability. 113: 119–134. doi:10.1016/j.polymdegradstab.2014.12.014.

[5] Chernyshev, E. A.; Aksenov, V. I.; Ponomarev, V. V.; Golubtsov, S. A.; Bugerenko, E. F. (1972). "Synthesis and reactions of 10-chloro-9,10-dihydro-10-phospha-9-oxaphenanthrene [6-chloro-6H-dibenz[c,1][1,2]oxaphosphorin]". Zhurnal Obshchei Khimii. 42: 93-6.

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