693006
(S)-SEGPHOS®
≥94%
Synonym(s):
(S)-(−)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole
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About This Item
Empirical Formula (Hill Notation):
C38H28O4P2
CAS Number:
Molecular Weight:
610.57
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
MDL number:
Quality Segment
assay
≥94%
form
solid
optical activity
[α]20/D -11°, c = 0.5 in chloroform
reaction suitability
reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation
mp
231-235 °C
functional group
phosphine
SMILES string
P(c8ccccc8)(c7ccccc7)c1c(c6c(cc1)OCO6)c2c3c(ccc2P(c5ccccc5)c4ccccc4)OCO3
InChI
1S/C38H28O4P2/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30/h1-24H,25-26H2
InChI key
RZZDRSHFIVOQAF-UHFFFAOYSA-N
Application
Chiral biaryl bisphosphine catalytic ligand used for:
- Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
- Stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydes
- Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives
- Diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex
- Preparation of dihydroisoquinolinones via nickel-catalyzed denitrogenative annulation of benzotriazinones with 1,3-dienes and alkenes
- Stereoselective preparation of indanol derivatives via Rh-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes
Legal Information
Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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