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481084

rac-BINAP

Name: rac-BINAP
Brand: ALDRICH

97%

Synonym(s):

(±)-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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About This Item

Linear Formula:

[(C₆H₅)₂PC₁₀H₆-]₂

CAS Number:

98327-87-8

Molecular Weight:

622.67

UNSPSC Code:

12352005

PubChem Substance ID:

24871738

NACRES:

NA.22

Beilstein/REAXYS Number:

5321443

MDL number:

MFCD00010805

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Properties

product line

Buchwald Ligand

Quality Level

200

assay

97%

reaction suitability

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

283-286 °C (lit.)

functional group

phosphine

greener alternative category

Aligned

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

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

Description

General description

Racemic version of BINAP.

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product falls under category 12 PAP and aligns with the Green Chemistry Principle of Catalysis. It is an outstanding chiral ligand for asymmetric hydrogenation catalysis, providing extremely high enantioselective recognition. Click here for more information.

Application

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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