1031-13-6

Basic information

• Product Name: 5-phenyl-5H-benzo[b]phosphindole 5-oxide
• Synonyms: 5H-benzo[b]phosphindole, 5-phenyl-, 5-oxide; 5-Phenyl-5H-benzo[b]phosphindole 5-oxide
• CAS NO: 1031-13-6
• Molecular Formula: C₁₈H₁₃OP
• Molecular Weight: 276.269
• Mol File: 1031-13-6.mol

Chemical Properties

• Boiling Point: 510.4°C at 760 mmHg
• Flash Point: 262.5°C
• Density: 1.27g/cm³
• Vapor Pressure: 4.98E-10mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: 5-phenyl-5H-benzo[b]phosphindole 5-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenyl-5H-benzo[b]phosphindole 5-oxide(1031-13-6)
• EPA Substance Registry System: 5-phenyl-5H-benzo[b]phosphindole 5-oxide(1031-13-6)

Safety Data

• Hazardous Substances Data: 1031-13-6(Hazardous Substances Data)

Upstream product

• 1088-00-2 9-phenyl-9-phosphafluorene 
• 98468-95-2 biphenyl-2-yl-phenyl-phosphinic acid 
• 644-97-3 Dichlorophenylphosphine 
• 2236-52-4 2,2'-diiodobiphenyl 
• 594-19-4 tert.-butyl lithium 
• 791-28-6 Triphenylphosphine oxide 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 1942-82-1 [1,1′-biphenyl]-2-yldimethylphosphine oxide 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 90-43-7 2-Phenylphenol 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 132-65-0 dibenzothiophene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 603-35-0 triphenylphosphine 

Downstream Products

• 137935-97-8 <(3-trimethylsilyl)-2,2'-biphenylylene>phenylphosphine oxide 
• 1942-82-1 [1,1′-biphenyl]-2-yldimethylphosphine oxide 
• 1354049-83-4 1-phenyldibenzophospholonium chloride 
• 1354049-96-9 5-phenyl-5H-dibenzophosphole borane 
• 1323156-90-6 [1,1'-biphenyl]-2-yl(phenyl)phosphine oxide 
• 137936-02-8 <3'-(trimethylsilyl)-2-biphenylyl>diphenylphosphine oxide 
• 17938-21-5 3-(Trimethylsilyl)biphenyl 
• 30469-82-0 α-phenyl[1,1'-biphenyl]-2-methanol 
• 92-52-4 biphenyl 

Relevant articles and documents

First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane

P-Hydroxytetraorganophosphorane, the long-postulated intermediate in phosphonium salt and ylide hydrolysis, has been observed and characterised by low temperature NMR, finally definitively establishing its involvement in these reactions. The results require modification of the previously accepted mechanism for ylide hydrolysis: P-hydroxytetraorganophosphorane is generated directly by 4-centre reaction of ylide with water. This journal is

Aryne-Induced SNAr/Dearylation Strategy for the Synthesis of Fluorinated Dibenzophospholes from Triarylphosphines via a P(V) Intermediate

We report on a method for the synthesis of fluorinated dibenzophospholes using triarylphosphine via dearylative annulation with an aryne. This intermolecular annulation allows the preparation of a variety of fluorinated dibenzophospholes from simple building blocks. The key to the success of this dearylative annulation is the formation of a five-coordinated tetraarylfluorophosphorane. In this work, we successfully synthesized stable tetraarylfluorophosphorane, the structure of which was unambiguously determined by X-ray crystallography.

Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation

A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo-fused derivatives to be converted to a variety of exotic heteroles. This transformation involves 1) the efficient generation of key 1,4-dianions by means of desulfurative dilithiation with lithium powder and 2) the subsequent trapping of the dianions with heteroatom electrophiles in a one-pot manner. Via the desulfurative dilithiation, the sulfur atoms of thiophenes are replaced also with a carbon–carbon double bond or a 1,2-phenylene for the construction of benzene rings.

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.

Homogeneous Palladium-Catalyzed Selective Reduction of 2,2′-Biphenols Using HCO 2H as Hydrogen Source

An efficient homogeneous palladium-catalyzed selective deoxygenation of 2,2′-biphenols by reduction of aryl triflates with HCO 2H as the hydrogen source is reported. This protocol complements the current method based on heterogeneous Pd/C-catalyzed hydrogenation with hydrogen gas. This process provided the reduction products in good to excellent yields, which could be readily converted to various synthetically useful molecules, especially ligands for catalytic synthesis.

Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator

The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical.

PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles

An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C?N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.

Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon-Phosphorus Bonds by Nickel Catalysis

The nickel-catalyzed cyclization of bisphosphine derivatives to form various phosphacycles is reported. The reaction proceeds via the cleavage of two carbon-phosphorus bonds of the bisphosphine. Unlike the previously reported palladium catalysts, the use

Synthesis of Dibenzophospholes by Tf2O-Mediated Intramolecular Phospha-Friedel-Crafts-Type Reaction

A Tf2O-mediated intramolecular phospha-Friedel-Crafts-type reaction of secondary biarylphosphine oxides has been developed. The reaction is promoted simply by Tf2O to form the corresponding dibenzophospholes under metal-free conditio

Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds

The free-radical arylation of H-phosphinates and related compounds was examined. A practical catalytic process with the air as the oxidant could not be found. However, an inexpensive and robust methodology was developed, using catalytic Mn(II) as the radi