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692395

Sigma-Aldrich

(R)-SEGPHOS®

≥94%

Synonym(s):

(R)-(+)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, [4(R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[diphenylphosphine]

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About This Item

Empirical Formula (Hill Notation):
C38H28O4P2
CAS Number:
244261-66-3
Molecular Weight:
610.57
MDL number:
MFCD09753005
UNSPSC Code:
12352005
PubChem Substance ID:
329761491
NACRES:
NA.22

Assay

≥94%

form

powder

optical activity

[α]20/D +11°, c = 0.5 in chloroform

mp

168-172 °C

SMILES string

C1Oc2ccc(P(c3ccccc3)c4ccccc4)c(c2O1)-c5c6OCOc6ccc5P(c7ccccc7)c8ccccc8

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
Catalytic ligand used for:
  • Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes
  • Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
  • Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
  • Preparation of chiral silylated homoallylic alcohols and diols by asymmetric addition of alcohols and aldehydes to silylbutadienes catalyzed by ruthenium complexes
  • Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
  • Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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