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Merck

481084

Sigma-Aldrich

rac-BINAP

97%

Synonym(e):

(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalin, 2,2′-Bis-(diphenylphosphino)-1,1′-binaphthalin, (±)-1,1′-Binaphthalin-2,2′-diyl-bis-(diphenylphosphin), (±)-BINAP, [1,1′-Binaphthalin]-2,2′-diylbis-[diphenylphosphin]

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5 G
CHF 109.00
25 G
CHF 324.00
100 G
CHF 1’030.00
500 G
CHF 5’030.00

CHF 109.00


Voraussichtliches Versanddatum25. März 2025


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5 G
CHF 109.00
25 G
CHF 324.00
100 G
CHF 1’030.00
500 G
CHF 5’030.00

About This Item

Lineare Formel:
[(C6H5)2PC10H6-]2
CAS-Nummer:
Molekulargewicht:
622.67
Beilstein:
5321443
MDL-Nummer:
UNSPSC-Code:
12352005
PubChem Substanz-ID:
NACRES:
NA.22

CHF 109.00


Voraussichtliches Versanddatum25. März 2025


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Qualitätsniveau

Assay

97%

Eignung der Reaktion

reaction type: Cross Couplings
reagent type: ligand
reaction type: Acylations

reagent type: ligand
reaction type: Arylations

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: C-C Bond Formation

reagent type: ligand
reaction type: Decarboxylations

reagent type: ligand
reaction type: Stille Coupling

mp (Schmelzpunkt)

283-286 °C (lit.)

Funktionelle Gruppe

phosphine

SMILES String

P(c8ccccc8)(c7ccccc7)c1c(c6c(cc1)cccc6)c2c3c(ccc2P(c5ccccc5)c4ccccc4)cccc3

InChI

1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChIKey

MUALRAIOVNYAIW-UHFFFAOYSA-N

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Allgemeine Beschreibung

Racemische Version von BINAP.[1]

Anwendung

Ligand, der für die Herstellung von Demethylthiocholchinen in einer palladiumkatalysierten Arylaminkupplung eingesetzt wird.[2] Wird mit Cu(II) eingesetzt, um die Addition von Arylsulfonamiden zu Styrolen und Olefinen zu katalysieren.[3] Aminierung von Terpyridinen mit Pd-Katalysatoren.[4]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Advanced Synthesis & Catalysis, 345, 15-32 (2003)
Akira Sakakura et al.
Nature protocols, 2(7), 1746-1751 (2007-07-21)
A protocol for ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by bulky diarylammonium pentafluorobenzenesulfonate is described. We also present procedures for the synthesis of N-(2,6-diisopropylphenyl)-N-mesitylammonium pentafluorobenzenesulfonate. The present ester condensation proceeds well under mild conditions even
Tetrahedron Letters, 47, 5079-5079 (2006)
Organometallics, 23, 3398-3416 (2004)
Jason G Taylor et al.
Organic letters, 8(16), 3561-3564 (2006-07-28)
[reaction: see text] Regioselective additions of arylsulfonamides to vinylarenes, norbornene, and cyclohexadiene were achieved using a copper-diphosphine catayst under mild reaction conditions. These processes appear to be ligand-accelerated.

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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