Skip to Content
Merck
All Photos(1)

Documents

Safety Information

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]

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Related Categories

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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

692395-VAR:
692395-50MG:
692395-100MG:
692395-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Takasago Ligands

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service