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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:
210169-54-3
Molecular Weight:
610.57
UNSPSC Code:
12352005
PubChem Substance ID:
329761551
NACRES:
NA.22
MDL number:
MFCD09753005
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Quality Level

100

assay

≥94%

form

solid

optical activity

[α]20/D -11°, c = 0.5 in chloroform

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

Takasago Ligands and Complexes for Asymmetric Reactions
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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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ9475
MKCG8574
MKCD7145
MKBX0849V
MKBS0885V

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Articles

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

Global Trade Item Number

SKUGTIN
693006-50MG04061832625027
693006-100MG04061832768809