1091-27-6

Basic information

• Product Name: 10-phenyl-10H-phenoxaphosphinine 10-oxide
• Synonyms: 10H-Phenoxaphosphine, 10-phenyl-, 10-oxide; 10-Phenylphenoxaphosphine 10-oxide; Phenoxaphosphine, 10-phenyl-, 10-oxide
• CAS NO: 1091-27-6
• Molecular Formula: C₁₈H₁₃O₂P
• Molecular Weight: 292.2684
• Mol File: 1091-27-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 490.4°C at 760 mmHg
• Flash Point: 263.6°C
• Density: 1.31g/cm³
• Vapor Pressure: 2.75E-09mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 10-phenyl-10H-phenoxaphosphinine 10-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 10-phenyl-10H-phenoxaphosphinine 10-oxide(1091-27-6)
• EPA Substance Registry System: 10-phenyl-10H-phenoxaphosphinine 10-oxide(1091-27-6)

Safety Data

• Hazardous Substances Data: 1091-27-6(Hazardous Substances Data)

Usage

Chemical structure

A phosphorous atom with a cyclic ring structure containing oxygen and a phenyl group attached at the 10th position.

Application in organic synthesis

Commonly used as a catalyst in various chemical reactions.

Flame retardant potential

Studied for its potential as a flame retardant due to its phosphorus content.

Medical research

Shown promise in inhibiting the growth of cancer cells, making it a potential candidate for anti-cancer drugs.

Electronic and optical properties

Investigated for its use in the development of organic light emitting diodes (OLEDs) due to its unique electronic and optical properties.

Molecular weight

Approximately 286.26 g/mol (based on the atomic weights of the constituent elements).

Solubility

Soluble in organic solvents such as dichloromethane, tetrahydrofuran, and acetone.

Stability

Relatively stable under normal conditions, but may decompose upon exposure to high temperatures or strong acids/bases.

Synthesis methods

Can be synthesized through various methods, such as the reaction of phenol with phosphorus trichloride followed by oxidation with hydrogen peroxide.

Upstream product

• 1225-16-7 10-phenyl-10H-phenoxaphosphinine 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 324-02-7 2-phenoxybenzenediazonium tetrafluoroborate 
• 60671-89-8 1-(2-bromophenoxy)-2-nitrobenzene 
• 101-84-8 diphenylether 
• 36712-28-4 bis(2-methoxyphenyl)(phenyl) phosphine oxide 
• 166330-10-5 bis[2-(diphenylphosphino)phenyl] ether 
• 958244-59-2 2-bromo-1-(2-iodophenoxy)benzene 
• 95-56-7 2-hydroxybromobenzene 
• 70787-31-4 2-amino-2'-bromo-diphenyl ether 
• 13381-22-1 o,o'-dilithio-diphenyl ether 

Downstream Products

• 1093-62-5 phenyl(o-phenoxyphenyl)phosphinic acid 
• 112122-94-8 bis(2-hydroxyphenyl)phenyl-λ⁵-phosphanone 
• 94407-54-2 2-hydroxyphenyl(phenyl)phosphinic acid 

Relevant articles and documents

New Access to Six-Membered Phosphacycle Annulated Polyaromatic Ring System

A facile Ag-catalyzed intramolecular C–P bond formation reaction from easily accessible phosphine oxides has been developed. Several new heteroatoms fused π-conjugated molecules were synthesized from this procedure with their structures confirmed by X-ray

Palladium-catalyzed cyclization of bisphosphines to phosphacycles via the cleavage of two carbon-phosphorus bonds

A catalytic method for the synthesis of dibenzophosphole derivatives using bisphosphines as the starting material is developed. The reaction proceeds through the cleavage of two carbonphosphorus bonds of the bisphosphine substrate. The reaction can also be used in the synthesis of six-membered phosphacycles.

Experimental and quantum chemical studies of 2-phosphinylphenol derivatives

Carbon-oxygen bonds ortho to a phosphoryl group in triarylphosphine oxides undergo cleavage when the oxides are either fused with potassium hydroxide or treated with potassium tert-butoxide in refluxing toluene, presumably through a nucleophilic addition-elimination mechanism. Thus, bis(2-hydroxyphenyl)phenylphosphine oxide is produced along with the expected 2-phenoxyphenyl(phenyl)phosphinic acid from 10-phenyl-10H-phenoxaphosphine 10-oxide. The latter starting material is also produced, together with bis(2-hydroxyphenyl)phenylphosphine oxide, when bis(2-methoxyphenyl)phenylphosphine oxide is fused with potassium hydroxide. Fusion of bis(2-methoxyphenyl)phenylphosphine oxide with sodium hydroxide, however, yields 2-hydroxyphenyl(phenyl)phosphinic acid. Ab initio quantum chemical studies confirm that the downfield 31P chemical shift that is observed in 2-phosphinylphenols is due to hydrogen bonding to the phosphoryl group.