Allyldiphenylphosphine oxide
Allyldiphenylphosphine oxide (CAS: 4141-48-4) is a chemical compound with the molecular formula H₂C=CHCH₂P(C₆H₅)₂(O) and a molecular weight of 242.25 g/mol. This phosphine oxide derivative serves as a valuable reactant in various organic synthesis applications, including the preparation of substituted silanes and alcohols, and in catalytic processes like olefin isomerization and cross-metathesis. Its utility extends to complex cycloaddition reactions.
- IUPAC
- Diphenyl-2-propenylphosphine oxide,NSC 616249,NSC 98715
- Synonyms
- Diphenyl-2-propenylphosphine oxideNSC 616249NSC 98715
Preparation of Substituted Silanes and Alcohols
Allyldiphenylphosphine oxide is employed as a reactant in the preparation of α-substituted alkylsilanes through regio- and chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes. Subsequently, these silanes can be converted to α-substituted alcohols via Fleming-Tamao oxidation.
Catalytic Olefin Isomerization
This compound participates in olefin isomerization reactions, particularly when supported by Grubbs' catalysts immobilized within a hydrophobic polydimethylsiloxane (PDMS) matrix. It also facilitates the isomerization of allyl groups to propenyl groups in the presence of a second-generation Grubbs Ru catalyst.
Diels-Alder Reactions
Allyldiphenylphosphine oxide is utilized in diastereotopic group-selective intramolecular Diels-Alder reactions, leading to the synthesis of complex cyclic structures such as C9-substituted trans-hydrindene.
Olefin Cross-Metathesis
It serves as a substrate in Ruthenium-catalyzed olefin cross-metathesis reactions with vinyl and allyl phosphine oxides to yield alkenyl phosphine oxides and bis-phosphine oxides.
| Molecular weight | 242.25 |
|---|---|
| Linear formula | H2C=CHCH2P(C6H5)2(O) |
| Assay | 97% |
| Application | Reactant for:• Preparaton of a-substituted alkylsilanes via regio- and chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes, and prepn. of α-substituted alcohols via Fleming-Tamao oxidation of alkylsilanes1• Olefin isomerization with Grubbs′ catalysts occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS)2• C9-substituted trans-hydrindene via diastereotopic group-selective intramolecular Diels-Alder reaction3• Isomerization of allyl group-containing compounds to propenyl group-containing compounds in the presence of a Grubbs second-generation Ru catalyst4• Ruthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides to give alkenyl phosphine oxides and bis-phosphine oxides5 |
| Melting point | 110-114 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Allyldiphenylphosphine oxide used for?
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Allyldiphenylphosphine oxide is used as a reactant in organic synthesis for preparing substituted silanes and alcohols, in olefin isomerization, Diels-Alder reactions, and olefin cross-metathesis.
What are the CAS number and molecular formula for Allyldiphenylphosphine oxide?
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The CAS number for Allyldiphenylphosphine oxide is 4141-48-4, and its linear molecular formula is H₂C=CHCH₂P(C₆H₅)₂(O).
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Allyldiphenylphosphine oxide with a minimum purity of 97%. We do not represent this product as USP, BP, or EP grade.
What are the safety and handling precautions for Allyldiphenylphosphine oxide?
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Allyldiphenylphosphine oxide is a Warning substance that causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Appropriate personal protective equipment, including a dust mask (type N95 US), eyeshields, and gloves, should be used. Ensure adequate ventilation.
How is Allyldiphenylphosphine oxide packed, shipped, and exported?
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Allyldiphenylphosphine oxide is available for export globally by Tech Serve Solutions. Specific packaging details will be provided upon inquiry.
How can I request a sample or a quote for Allyldiphenylphosphine oxide?
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To request a sample or a quote, please contact the Tech Serve Solutions sales team through our official website or listed contact channels.
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