Skip to Content
MilliporeSigma

Skip To

481084

rac-BINAP

greener alternative

Greener Alternative

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]

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View
Size/SKUAvailabilityPrice
5 g
Check Cart for Availability
$135.00
25 g
Check Cart for Availability
$392.00
$294.00
100 g
Check Cart for Availability
$1,500.00
$1,125.00
500 g

Estimated to ship onJuly 28, 2026fromMILWAUKEE

$7,120.00

About This Item

Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Beilstein/REAXYS Number:
5321443
MDL number:

$135.00


Check Cart for Availability

Request a Custom Order
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


product line

Buchwald Ligand

Quality Segment

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

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

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.[1] Used with Cu (II) to catalyze addition of arylsulfonamides to styrenes and olefins.[2] Amination of terpyridines with Pd catalysis.

Compare Similar Items

View Full Comparison

Show Differences

1 of 1

This Item
295817900340693065
reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: C-C Bond Formation, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Acylations, reagent type: ligand
reaction type: Decarboxylations

reaction suitability

-

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings

reaction suitability

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

assay

97%

assay

97%

assay

-

assay

-

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

mp

283-286 °C (lit.)

mp

239-241 °C (lit.)

mp

-

mp

239-241 °C (lit.)

greener alternative category

Aligned

greener alternative category

-

greener alternative category

-

greener alternative category

-

sustainability

Greener Alternative Product

sustainability

-

sustainability

-

sustainability

-


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

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

Visit the Document Library



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

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters