(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Chemical Properties

Melting point:

231-235 °C

Boiling point:

715.4±60.0 °C(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

off-white

optical activity

[α]20/D -11°, c = 0.5 in chloroform

InChIKey

RZZDRSHFIVOQAF-UHFFFAOYSA-N

Safety Information

WGK Germany 

3

HS Code 

2932.99.7000

(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Usage And Synthesis

Reaction

1. Biaryl bisphosphine ligand with narrow dihedral angle. The SEGPHOS® ligand has been applied to a variety of metal catalyzed reactions. In many cases, yields and enantioselectivities, exceed results obtained earlier using BINAP.
2. As ruthenium complex, SEGPHOS® generally gives higher levels of chiral induction in asymmetric hydrogenations of α,β,and γ-functionalized ketones. See ruthenium complexes 44-0096, 44-0518, 44-0168.
3. Used in Rh-catalyzed transformations such as: (a) 1,4-addition of boronic acids to coumarins,4 (b) addition of titanium reagents to imines, (c) cotrimerization of alkenes and acetylenes, (d) double [2+2+2] cycloaddition,11 (e) indanone formation.12a,b
4. Used in Pd-catalyzed transformations such as: (a) cycloaddition of 1,6-enyne, (b) arylative cyclization of allenyl aldehydes with boronic acids,13 (c) synthesis of chromans.
5. Used in Cu-catalyzed transformations such as: (a) nitroso Diels-Alder, (b) reductive aldol condensation, (c) conjugate reduction of unsaturated sulfones,15 and phophonates.
6. Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates. 

(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS(210169-54-3)Related Product Information

• (R)-SEGPHOS
• N-[(1R,2R)-1,2-Diphenyl-2-(2-(4-Methylbenzyloxy)ethylaMino)-ethyl]-4-Methylbenzene sulfonaMide(chloro)rutheniuM(II) (R,R)-Ts-DENEB 1333981-84-2
• Chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl} [(2R)-(-)-1-(4-Methoxyphenyl)- 1 (4-Methoxyphenyl-kC)-3- Methyl-1,2-butanediaMine]rutheniuM(II) (R)-RUCY XylBINAP
• (S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS
• Dichloro{(S)-(-)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}[(2S)-(+)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II)
• (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS
• (R)-DIFLUORPHOS(TM)
• Diacetato[(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II)
• Diacetato{(R)-(+)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}ruthenium(II)
• (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS
• Diacetato[(S)-(-)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole]ruthenium(II)
• Dichloro{(R)-(+)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}[(2R)-(-)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II)
• Chloro[(R)-(-)5,5μ-bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4μ-bi-1,3-benzodioxole](p-cymene)ruthenium(II) chloride
• (S)-(-)-2,2'-BIS[3'',4''-METHYLENEOXYPHENYLPHOSPHINO]-5,6-5',6'-DIMETHYLENEOXY-BIPHENYL
• Dimethylammonium dichlorotri(μ-chloro)bis[(R)-(+)-5,5μ-bis[di(3,5-xylyl)phosphino]-4,4μ-bi-1,3-benzodioxole]diruthenate(II)
• Dichloro{(S)-(-)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}[(1S,2S)-(-)-1,2-diphenylethylenediamine]ruthenium(II)
• Dichloro{(R)-(+)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}[(1R,2R)-(+)-1,2-diphenylethylenediamine]ruthenium(II)
• Chloro{(R)-(+)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole}(p-cymene)ruthenium(II)chloride