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MilliporeSigma

481084

Sigma-Aldrich

rac-BINAP

97%

Sinónimos:

(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (±)-BINAP, [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine]

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5 G
$124.00
25 G
$368.00
100 G
$1,410.00
500 G
$6,690.00

$124.00


Fecha estimada de envío08 de mayo de 2025DesdeMILWAUKEE


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5 G
$124.00
25 G
$368.00
100 G
$1,410.00
500 G
$6,690.00

About This Item

Fórmula lineal:
[(C6H5)2PC10H6-]2
Número de CAS:
Peso molecular:
622.67
Beilstein:
5321443
Número MDL:
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
NACRES:
NA.22

$124.00


Fecha estimada de envío08 de mayo de 2025DesdeMILWAUKEE


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Ensayo

97%

idoneidad de la reacción

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

283-286 °C (lit.)

grupo funcional

phosphine

cadena SMILES

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

Clave InChI

MUALRAIOVNYAIW-UHFFFAOYSA-N

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Descripción general

Racemic version of BINAP.[1]

Aplicación

Ligand employed in a palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.[2] Used with Cu (II) to catalyze addition of arylsulfonamides to styrenes and olefins.[3] Amination of terpyridines with Pd catalysis.[4]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Certificados de análisis (COA)

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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. How is shipping temperature determined? And how is it related to the product storage temperature?

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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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  2. How can I determine the shelf life / expiration / retest date of this product?

    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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