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693065

(R)-BINAP

Synonym(s):

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP

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Size/SKUAvailabilityPrice
100 mg

Available to ship TODAY

$36.70
500 mg

Available to ship TODAYfromMILWAUKEE

$93.40

About This Item

Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:

$36.70


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form

crystals

Quality Segment

optical activity

[α]20/D +222°, c = 0.5% in benzene

reaction suitability

reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation, reagent type: chrial catalyst
reaction type: Asymmetric synthesis

mp

239-241 °C (lit.)

functional group

phosphine

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccccc7)c8ccccc8

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

Application

(R)-BINAP reacts with allylpalladium(II) chloride dimer to form a BINAP-palladium catalyst, which can catalyze the asymmetric allylation of 1,3-diketones to form chiral 2,2-dialkyl-1,3-diketones. It may also be used in the preparation of chirally stabilized rhodium nanoparticles, which can be used as a catalyst for the asymmetric hydroformylation of styrene and vinyl acetate.

Legal Information

Sold in collaboration with Takasago for research purposes only.

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295817693049693014
description

-

description

97%

description

-

description

technical grade

reaction suitability

reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation, reaction type: Asymmetric synthesis

reaction suitability

-

reaction suitability

reaction type: Stille Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Cross Couplings, reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation, reaction type: Suzuki-Miyaura Coupling, reaction type: Hiyama Coupling, reaction type: Asymmetric synthesis, reaction type: Negishi Coupling

reaction suitability

reaction type: Asymmetric synthesis, reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

form

crystals

form

solid

form

solid

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

optical activity

[α]20/D +222°, c = 0.5% in benzene

optical activity

[α]19/D +233°, c = 0.3 in toluene

optical activity

[α]20/D +162°, c = 0.5 in benzene

optical activity

-

mp

239-241 °C (lit.)

mp

239-241 °C (lit.)

mp

254-258 °C

mp

-


Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)



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Questions

1–2 of 2 Questions  
  1. 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/418/501/product-dating-information-06-25-mk.pdf

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

    1 answer
    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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