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Phosphines [Chemical Structural Class]

 Phosphorus belongs to group 15 in the periodic table, the same as nitrogen, and it binds with carbon to form various organophosphate compounds. However, since nitrogen belongs to the second-period and phosphorus to the third, they differ in atomic size, ionization energy and electronegativity etc. Therefore, organophosphate compounds show a characteristic reactivity which organic nitrogen compounds do not have, and it is utilized as a versatile reaction reagent in organic synthesis. For example, phosphorus has a high affinity for oxygen: phosphorus ylide and phosphonate are utilized for the Wittig reaction and the Horner-Emmons reaction, respectively, and it extracts oxygen from aldehydes to produce olefins. Phosphine extracts oxygen from alcohols to produce esters in the Mitsunobu reaction.
 Another feature of phosphine includes bearing a soft lone pair. Therefore, it forms comparatively stable complexes with transition metals such as palladium. This transition metal complex is used frequently as a catalyst in reactions such as the Suzuki-Miyaura cross-coupling reaction and the Heck reaction.1) Although phosphine also has a trigonal pyramidal structure like amines, its rotational barrier energy is considerably higher than the corresponding amine. Therefore, a phosphine which has three different substituents has optical isomers. This optically-active phosphine is utilized for asymmetric syntheses as a P-chiral ligand.2) In this section, we introduce tri-substituted alkyl and aryl phosphines, such as tricyclohexylphosphine and triphenylphosphine.

Literature

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Product Number T0361
CAS RN 998-40-3
Purity / Analysis Method: >95.0%(GC)

Product Number T1643
CAS RN 5518-52-5
Purity / Analysis Method: >98.0%(GC)

Product Number T1024
CAS RN 6163-58-2
Purity / Analysis Method: >97.0%(GC)

Product Number T0503
CAS RN 4731-53-7
Purity / Analysis Method: >85.0%(GC)

Product Number T1757
CAS RN 3053-68-7
Purity / Analysis Method: >97.0%(T)

Product Number T2248
CAS RN 7650-88-6
Purity / Analysis Method: >95.0%(T)

Product Number T2484
CAS RN 1259-35-4
Purity / Analysis Method: >95.0%(GC)

Product Number T3005
CAS RN 4731-65-1
Purity / Analysis Method: >97.0%(HPLC)

Product Number T1656
CAS RN 51805-45-9
Purity / Analysis Method: >98.0%(T)

Product Number T1666
CAS RN 24171-89-9
Purity / Analysis Method: >96.0%(GC)

Product Number T0519
CAS RN 603-35-0
Purity / Analysis Method: >95.0%(T)

Product Number T1789
CAS RN 2049-55-0
Purity / Analysis Method: >97.0%(T)

Product Number:   T0361 | Purity / Analysis Method:   >95.0%(GC)

Product Number:   T1643 | Purity / Analysis Method:   >98.0%(GC)

Product Number:   T1024 | Purity / Analysis Method:   >97.0%(GC)

Product Number:   T0503 | Purity / Analysis Method:   >85.0%(GC)

Product Number:   T1757 | Purity / Analysis Method:   >97.0%(T)

Product Number:   T2248 | Purity / Analysis Method:   >95.0%(T)

Product Number:   T2484 | Purity / Analysis Method:   >95.0%(GC)

Product Number:   T3005 | Purity / Analysis Method:   >97.0%(HPLC)

Product Number:   T1656 | Purity / Analysis Method:   >98.0%(T)

Product Number:   T1666 | Purity / Analysis Method:   >96.0%(GC)

Product Number:   T0519 | Purity / Analysis Method:   >95.0%(T)

Product Number:   T1789 | Purity / Analysis Method:   >97.0%(T)

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