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

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9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO).svg
Names
Other names
3,4:5,6-Dibenzo-2H-1,2-oxaphosphorin-2-oxide
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 252-813-7
PubChem CID
UNII
  • 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
  • C1=CC=C2C(=C1)C3=CC=CC=C3P(=O)O2
Properties
C12H9O2P
Molar mass 216.176 g·mol−1
Appearancewhite 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).

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]

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<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid. Organophosphates are best known for their use as pesticides.

<span class="mw-page-title-main">Aluminium chloride</span> Chemical compound

Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.

<span class="mw-page-title-main">Phosphonium</span> Family of polyatomic cations containing phosphorus

In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Antimony trioxide</span> Chemical compound

Antimony(III) oxide is the inorganic compound with the formula Sb2O3. It is the most important commercial compound of antimony. It is found in nature as the minerals valentinite and senarmontite. Like most polymeric oxides, Sb2O3 dissolves in aqueous solutions with hydrolysis. A mixed arsenic-antimony oxide occurs in nature as the very rare mineral stibioclaudetite.

<span class="mw-page-title-main">Phosphoryl chloride</span> Chemical compound

Phosphoryl chloride is a colourless liquid with the formula POCl3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters.

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

<span class="mw-page-title-main">2-Phenylphenol</span> Chemical compound

2-Phenylphenol, or o-phenylphenol, is an organic compound. In terms of structure, it is one of the monohydroxylated isomers of biphenyl. It is a white solid. It is a biocide used as a preservative with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.

<span class="mw-page-title-main">Oxazines</span> E heterocyclic organic compounds containing one oxygen and one nitrogen atom

Oxazines are heterocyclic organic compounds containing one oxygen and one nitrogen atom in a cyclohexa-1,4-diene ring. Isomers exist depending on the relative position of the heteroatoms and relative position of the double bonds.

<span class="mw-page-title-main">Trimethyl phosphite</span> Chemical compound

Trimethyl phosphite is an organophosphorus compound with the formula P(OCH3)3, often abbreviated P(OMe)3. It is a colorless liquid with a highly pungent odor. It is the simplest phosphite ester and finds used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The molecule features a pyramidal phosphorus(III) center bound to three methoxy groups.

<span class="mw-page-title-main">Chlorodiphenylphosphine</span> Chemical compound

Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is useful reagent for introducing the Ph2P group into molecules, which includes many ligands. Like other halophosphines, Ph2PCl is reactive with many nucleophiles such as water and easily oxidized even by air.

<span class="mw-page-title-main">Diphenyl ether</span> Chemical compound

Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications.

<span class="mw-page-title-main">Tetrakis(hydroxymethyl)phosphonium chloride</span> Chemical compound

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. It is a white water-soluble salt with applications as a precursor to fire-retardant materials and as a microbiocide in commercial and industrial water systems.

Dopo may refer to

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

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Kaushal Kishore (1942–1999) was an Indian polymer chemist and head of the department of inorganic and physical Chemistry at the Indian Institute of Science (IISc). He was known for his researches on thermochemistry and combustion of polymers. and was an elected fellow of the National Academy of Sciences, India, Indian National Science Academy, and the Indian Academy of Sciences. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, in 1988, for his contributions to chemical sciences.

<span class="mw-page-title-main">Stibinin</span> Chemical compound

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References

  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.
  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.