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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.
B1112
(2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol
B1113
(2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol
B1137
1,2-Bis(diphenylphosphino)ethane
B1138
1,3-Bis(diphenylphosphino)propane
B1174
1,2-Bis(dimethylphosphino)ethane
B1246
1,4-Bis(diphenylphosphino)butane
B1405
(S)-(-)-BINAP
B1406
(R)-(+)-BINAP
B1959
1,6-Bis(diphenylphosphino)hexane
B1960
1,5-Bis(diphenylphosphino)pentane
B1982
Bis(diphenylphosphino)methane
B2003
trans-1,2-Bis(diphenylphosphino)ethylene
B2027
1,1'-Bis(diphenylphosphino)ferrocene
B2089
(S,S)-1,2-Bis[(tert-butyl)methylphosphino]ethane Bis(borane)
B2383
(±)-BINAP
B2630
2,2'-Bis(diphenylphosphino)biphenyl
B2704
(2S,3S)-(-)-Bis(diphenylphosphino)butane
B2709
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
B2710
1,1'-Bis(diisopropylphosphino)ferrocene
B2711
1,1'-Bis(di-tert-butylphosphino)ferrocene
B2717
4,6-Bis(diphenylphosphino)phenoxazine
B2867
Bis[2-(diphenylphosphino)phenyl] Ether
B3035
(R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane
B3036
(S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane
B3196
(R,R'')-2,2''-Bis(diphenylphosphino)-1,1''-biferrocene
B3428
1,2-Bis[bis(pentafluorophenyl)phosphino]ethane
B3449
(2R,3R)-(-)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene
B3450
(2S,3S)-(+)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene
B3953
(2-Bromophenyl)diphenylphosphine
B4272
1,1'-Bis(dichlorophosphino)ferrocene
B4530
1,8-Bis(diphenylphosphino)naphthalene
B4560
Bis(pentafluorophenyl)phenylphosphine
B4595
1,3-Bis[(di-tert-butylphosphino)oxy]benzene
B5239
4,5-Bis(dicyclohexylphosphino)-9,9-dimethylxanthene
B5301
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
B5302
(S,S)-(+)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
C0597
Chlorodiphenylphosphine
C1429
Cyclohexyldiphenylphosphine
C2979
cBRIDP®
C2980
Cy-cBRIDP®
C2981
Cy-vBRIDP®
C3201
Chlorodi(p-tolyl)phosphine
D1019
Diethylphenylphosphine
D2043
Sodium Diphenylphosphinobenzene-3-sulfonate
D2404
Diphenyl-1-pyrenylphosphine
D2411
Dicyclohexylphenylphosphine
D2471
Diphenyl-2-pyridylphosphine
D2478
4-(Dimethylamino)phenyldiphenylphosphine
D2535
(R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine
D2536
(S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine
D2537
(R)-N,N-Dimethyl-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine
D2538
(S)-N,N-Dimethyl-1-[(R)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine
D2630
Diphenylpropylphosphine
D2766
4-Diphenylphosphinomethyl Polystyrene Resin cross-linked with 2% DVB (200-400mesh) (0.5-1.0mmol/g)
D2774
(R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl
D3242
2-(Diphenylphosphino)benzoic Acid
D3243
4-(Diphenylphosphino)benzoic Acid
D3387
2-(Di-tert-butylphosphino)biphenyl
D3388
2-(Dicyclohexylphosphino)biphenyl
D3389
2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl
D3834
1-[2-(Di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole
D4411
2-(Diphenylphosphino)benzaldehyde
D4498
(S)-(-)-DM-SEGPHOS®
D4499
(R)-(+)-DM-SEGPHOS®
D4500
(S)-(+)-DTBM-SEGPHOS®
D4501
(R)-(-)-DTBM-SEGPHOS®
D4531
(4-Dimethylaminophenyl)di-tert-butylphosphine
D4688
2-(Diphenylphosphino)biphenyl
D4781
Di-1-adamantylphosphine
D4825
3-(Diphenylphosphino)-1-propylamine
D4953
2-(Diphenylphosphino)benzonitrile
D5035
2-Dicyclohexylphosphino-2'-methylbiphenyl
D5036
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
D5037
2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl
D5038
2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl
D5039
2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl
D5663
Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine
D5664
Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine
E0519
Ethyldiphenylphosphine
I0583
Isopropyldiphenylphosphine
M1318
Methyldiphenylphosphine
M2103
1-Methyl-1-[4-(diphenylphosphino)benzyl]pyrrolidinium Bromide
P1176
(Pentafluorophenyl)diphenylphosphine
S0929
(S)-(-)-SEGPHOS®
S0930
(R)-(+)-SEGPHOS®
T0503
Tri-n-octylphosphine
T0519
Triphenylphosphine
T0861
Tris(4-methoxyphenyl)phosphine
T0862
Tri(p-tolyl)phosphine
T1005
Trihexylphosphine
T1024
Tri(o-tolyl)phosphine
T1025
Tri(m-tolyl)phosphine
T1165
Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide) (ca. 18% in Toluene, ca. 0.60mol/L)
T1614
Tris(2,6-dimethoxyphenyl)phosphine
T1643
Tri(2-furyl)phosphine
T1656
Tris(2-carboxyethyl)phosphine Hydrochloride
T1666
Tri(2-thienyl)phosphine
T1757
Triphenylborane - Triphenylphosphine Complex
T1789
Triphenylphosphine Borane
T2484
Tris(pentafluorophenyl)phosphine
T2526
Tris[3,5-bis(trifluoromethyl)phenyl]phosphine
T2900
Tris(4-fluorophenyl)phosphine
T3005
Tris(2-methoxyphenyl)phosphine
T3152
(R)-(+)-TolBINAP
T3153
(S)-(-)-TolBINAP
T3489
Trimethylphosphine
V0132
vBRIDP®
X0070
(R)-(+)-XylBINAP
X0071
(S)-(-)-XylBINAP

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