2409-61-2

Basic information

• Product Name: BIS(P-TOLYL)PHOSPHINE OXIDE
• Synonyms: Di-p-tolylphosphine oxide;Bis(4-Methylphenyl)phosphine Oxide;Bis (p-Methylphenyl) phosphine oxide;BIS(P-TOLYL)PHOSPHINE OXIDE;1-Methyl-4-[(4-Methylphenyl)phosphoryl]benzene
• CAS NO: 2409-61-2
• Molecular Formula: C₁₄H₁₅OP
• Molecular Weight: 230.24
• EINECS: 1308068-626-2
• Mol File: 2409-61-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 96°C(lit.)
• Boiling Point: 354.235 °C at 760 mmHg
• Flash Point: 168.035 °C
• Appearance: /
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: BIS(P-TOLYL)PHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(P-TOLYL)PHOSPHINE OXIDE(2409-61-2)
• EPA Substance Registry System: BIS(P-TOLYL)PHOSPHINE OXIDE(2409-61-2)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2409-61-2(Hazardous Substances Data)

Usage

Description

Bis(p-tolyl)phosphine oxide, also known as di-p-tolyl phosphine oxide, is an organic compound with the chemical formula (C6H4CH3)2P(O). It is a white powder that serves as an important intermediate in the synthesis of various organic compounds.

Uses

1. Organic Chemical Synthesis:
Bis(p-tolyl)phosphine oxide is used as an organic chemical synthesis intermediate for the production of a wide range of organic compounds. Its unique chemical properties make it a valuable building block in the creation of complex molecules.
2. Suzuki Reaction:
In the field of organic chemistry, Bis(p-tolyl)phosphine oxide is used as a catalyst in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. The Suzuki reaction is particularly useful in the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and advanced materials.
3. Chemical Industry:
Bis(p-tolyl)phosphine oxide is used in the chemical industry as a catalyst or reagent for various chemical reactions. Its ability to facilitate bond formation and its stability make it a preferred choice for numerous industrial applications.
4. Pharmaceutical Industry:
In the pharmaceutical industry, Bis(p-tolyl)phosphine oxide is utilized as a key intermediate in the synthesis of various drug molecules. Its role in creating complex structures is crucial for the development of new and effective medications.
5. Material Science:
Bis(p-tolyl)phosphine oxide is also used in the field of material science, where it contributes to the development of advanced materials with specific properties. Its involvement in the synthesis of these materials can lead to improved performance and novel applications.

InChI:InChI=1/C14H15OP/c1-11-3-7-13(8-4-11)16(15)14-9-5-12(2)6-10-14/h3-10,16H,1-2H3

Upstream product

• 1017-60-3 di-p-tolylphosphine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 762-04-9 phosphonic acid diethyl ester 
• 1019-71-2 chlorodi-p-tolylphosphane 
• 762-04-9 Diethyl phosphonate 
• 13685-92-2 (diethylamino)[bis(4-methylphenyl)]phosphine 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 

Downstream Products

• 15754-57-1 bis(4-methylphenyl)thiophosphinic acid-S-phenyl ester 
• 106649-34-7 (Di-p-tolyl-phosphinoyl)-methanol 
• 145290-28-4 N,N-Dibutyl-2-(di-p-tolyl-phosphinoyl)-acetamide 
• 137862-43-2 1-diphenylphosphinyl-2-di(p-tolyl)phosphinylpropane 
• 137862-44-3 C₃₀H₃₂O₂P₂ 
• 13685-32-0 di(n-tolyl)chloromethylphosphine oxide 
• 105875-86-3 3-(Di-p-tolyl-phosphinoyl)-propan-1-ol 
• 479578-14-8 {(R)-[2-(di-p-tolylphosphinoyl)naphthalen-1-yl](phenyl)methyl}methyl((1R')-1'-phenylethyl)amine 
• 479578-16-0 N-{(R)-[2-(di-p-tolylphosphinoyl)naphthalen-1-yl](phenyl)methyl}-N-((1'R)-1'-phenylethyl)acetamide 

Relevant articles and documents

Electrochemical Oxidative C–H Phosphonylation of thiazole derivatives in ambient conditions

We herein report a direct electrochemical dehydrogenative C–H phosphonylation of thiazoles derivatives with H2 evolution. Employing electricity as the green and sole oxidant, cheap metal as electrode, the anodic oxidation together with cathodic hydrogen evolution process provides a green and efficient strategy for C–H phosphonylation. A diverse range of phosphorus products were constructed under external metal and oxidant-free conditions at ambient temperature, featuring atom economy, simple operation and wide reaction scope.

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.