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663131

Sigma-Aldrich

RuPhos

greener alternative

98%

Synonym(s):

2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl

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1 G
MXP 1,618.00
5 G
MXP 5,955.00
25 G
MXP 19,587.00

MXP 1,618.00

Estimated to ship onMarch 29, 2025

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1 G
MXP 1,618.00
5 G
MXP 5,955.00
25 G
MXP 19,587.00

About This Item

Empirical Formula (Hill Notation):
C30H43O2P
CAS Number:
787618-22-8
Molecular Weight:
466.64
MDL number:
MFCD06798294
UNSPSC Code:
12352112
PubChem Substance ID:
24884189
NACRES:
NA.22

MXP 1,618.00

Estimated to ship onMarch 29, 2025

Request a Bulk Order

Quality Level

300

Assay

98%

form

solid

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

greener alternative product score

old score: 3
new score: 1
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greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

impurities

1-5% Bis(2′,6′-Diisopropoxybiphenyl)cyclohexylphosphine

mp

123-126 °C

functional group

phosphine

greener alternative category

Re-engineered,

SMILES string

CC(C)Oc1cccc(OC(C)C)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C30H43O2P/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25/h11-13,18-25H,5-10,14-17H2,1-4H3

InChI key

MXFYYFVVIIWKFE-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Atom Economy”, “Design for Energy Efficiency” and “Use of Renewable Feedstock”. Click here to view its DOZN scorecard.

Application

Bulky phosphine ligand used in a palladium-catalyzed cross-coupling of aminoethyltrifluoroborates with electron-poor aryl bromides.[1]

For small scale and high throughput uses, product is also available as ChemBeads (932205)

Legal Information

Usage subject to Patents: EP 1097158; JP 5758844; CA 2336691

related product

Product No.
Description
Pricing

918008

GPhos, ≥95%

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9145
SHBR5715
SHBN8257
0000244711
0000214596

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Gary A Molander et al.
Organic letters, 9(2), 203-206 (2007-01-16)
A set of phenethylamines has been successfully prepared via Suzuki-Miyaura cross-coupling of diverse potassium beta-aminoethyltrifluoroborates with aryl halides. The potassium beta-aminoethyltrifluoroborates were easily prepared via hydroboration of enamine and enamide precursors. [reaction: see text].
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon

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Questions

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  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/449/386/product-dating-information-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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