METHYLDIPHENYLPHOSPHINE Chemical Properties

Melting point:

117-118 °C

Boiling point:

120-122 °C1.5 mm Hg(lit.)

Density 

1.076 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.625(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

color 

Clear colorless to slightly yellow

Specific Gravity

1.076

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

743075

InChI

InChI=1S/C13H13P/c1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3

InChIKey

UJNZOIKQAUQOCN-UHFFFAOYSA-N

SMILES

P(C)(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

1486-28-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

17-23-24/25-36/37/39-26

WGK Germany 

3

F 

1-10

TSCA 

No

HS Code 

29420000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

METHYLDIPHENYLPHOSPHINE Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

Methyldiphenylphosphine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Application

Methyldiphenylphosphine is an important organophosphorus ligand widely used in catalytic chemistry and materials science. It often forms complexes with transition metals such as palladium, rhodium, and nickel as a monodentate ligand, catalyzing a variety of organic synthesis reactions, such as carbon-carbon coupling reactions (e.g., the Heck and Suzuki reactions), hydroformylation, and asymmetric hydrogenation, effectively enhancing the activity and selectivity of these reactions. Furthermore, due to its unique electronic and steric properties, it is also used in the synthesis of functional materials such as luminescent materials and liquid crystals, and as a protective agent for stabilizing nanoparticles, demonstrating its significant value in organic electronics and nanotechnology.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

Synthesis

The mainstream preparation method for methyldiphenylphosphine typically involves a nucleophilic substitution reaction between a Grignard reagent or an organolithium reagent and chlorodiphenylphosphine. The most common approach involves first preparing methylmagnesium bromide (CH₃MgBr) via a Grignard reaction, which is then added dropwise to a solution of chlorodiphenylphosphine in an inert solvent such as diethyl ether or tetrahydrofuran. After the reaction is complete, post-processing steps such as hydrolysis and extraction are performed to remove the byproduct magnesium chloride and unreacted starting materials. Finally, purification is performed by vacuum distillation or recrystallization to obtain the target product, methyldiphenylphosphine.

METHYLDIPHENYLPHOSPHINE(1486-28-8)Related Product Information

• 1,6-Bis(diphenylphosphino)hexane
• 1,1'-Bis(diphenylphosphino)ferrocene
• Bis(diphenylphosphino)methane
• 1,4-Bis(diphenylphosphino)butane
• TETRAPHENYLPHOSPHINE IMIDE
• DIPHENYL(PENTAFLUOROPHENYL)PHOSPHINE
• METHYLDIPHENYLPHOSPHINE OXIDE
• BIS(2-DIPHENYLPHOSPHINOETHYL)PHENYLPHOSPHINE
• TRIPHENYLPHOSPHINE DIBROMIDE
• BIS(PENTAFLUOROPHENYL)PHENYLPHOSPHINE
• (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
• 1,5-Bis(diphenylphosphino)pentane
• 1,2-Bis(diphenylphosphino)ethane
• Triphenylphosphine oxide
• 1,3-Bis(diphenylphosphino)propane
• CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE
• TETRAKIS(METHYLDIPHENYLPHOSPHINE)PALLADIUM(0)
• (1,5-CYCLOOCTADIENE)BIS(METHYLDIPHENYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE