| Identification | More | [Name]
METHYLDIPHENYLPHOSPHINE | [CAS]
1486-28-8 | [Synonyms]
DIPHENYLMETHYLPHOSPHINE
METHYLDIPHENYLPHOSPHINE
Methyldiphenylphsphine
Methyldiphenylphosphine,99%
Diphenylphosphinomethane | [EINECS(EC#)]
216-065-5 | [Molecular Formula]
C13H13P | [MDL Number]
MFCD00008508 | [Molecular Weight]
200.22 | [MOL File]
1486-28-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [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.)
| [Fp ]
>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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S17:Keep away from combustible material .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
1-10 | [TSCA ]
No | [HS Code ]
29420000 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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. |
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