Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

905240

Sigma-Aldrich

(R,R,R)-SPIRAP

≥95%

Synonym(s):

((1R,3R,3′R)-3,3′-diethyl-3H,3′H-1,1′-spirobi[isobenzofuran]-7,7′-diyl)bis(diphenylphosphane), (R)-CrabPhos

Sign Into View Organizational & Contract Pricing

Select a Size

50 MG
¥23,900

¥23,900

Estimated to ship onApril 05, 2025

Request a Bulk Order
All Photos(2)

Select a Size

Change View
50 MG
¥23,900

About This Item

Empirical Formula (Hill Notation):
C43H38O2P2
Molecular Weight:
648.71
MDL number:
MFCD32062477
UNSPSC Code:
12161600
NACRES:
NA.22

¥23,900

Estimated to ship onApril 05, 2025

Request a Bulk Order

Assay

≥95%

form

powder or crystals

reaction suitability

reagent type: ligand
reaction type: Asymmetric synthesis

mp

226-228 °C

SMILES string

CC[C@@H](O1)C2=C([C@@]1(O[C@@H]3CC)C4=C3C=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6)C(P(C7=CC=CC=C7)C8=CC=CC=C8)=CC=C2

InChI

1S/C43H38O2P2/c1-3-37-35-27-17-29-39(46(31-19-9-5-10-20-31)32-21-11-6-12-22-32)41(35)43(44-37)42-36(38(4-2)45-43)28-18-30-40(42)47(33-23-13-7-14-24-33)34-25-15-8-16-26-34/h5-30,37-38H,3-4H2,1-2H3/t37-,38-,43-/m1/s1

InChI key

PRORVWYPBRMLLA-FFUXEPPCSA-N

Related Categories

Application

(R,R,R)-SPIRAP is a chiral C2-symmetric spiroketal-containing ligand developed in the Nagorny lab for asymmetric catalysis. It can be used in variety of stereoselective transformations, including: Ir-catalyzed hydroarylation, Pd-catalyzed allylic alkylation, Pd-catalyzed Heck couplings, and Rh-catalyzed hydrogenation.[1]

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

Other Notes

Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

related product

Product No.
Description
Pricing

692395

(R)-SEGPHOS®, ≥94%

693006

(S)-SEGPHOS®, ≥94%

700835

(S)-Tol-SDP

700746

(S)-SDP, ≥95%

700851

(S)-Xyl-SDP

700843

(R)-Xyl-SDP

700754

(R)-SDP

905305

(S,S,S)-SPIRAP, ≥95%

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

905240-VAR:
905240-BULK:
905240-50MG:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCJ2892

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis.
Arguelles AJ, et al.
Angewandte Chemie (International Edition in English), 57(19), 5325-5329 (2018)
Alonso J Argüelles et al.
Angewandte Chemie (International ed. in English), 57(19), 5325-5329 (2018-02-24)
We present an expedient and economical route to a new spiroketal-based C2 -symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in

Related Content

Nagorny Group - Prof. Product Portal

Nagorny group designs SPIROL-based ligands for efficient catalysis, focusing on asymmetric transformations.

Questions

Reviews

No rating value

Active Filters

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