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718742

BrettPhos

greener alternative

Greener Alternative

98%, solid

Synonym(s):

2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl

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100 mg

Available to ship TODAYfromMILWAUKEE

$37.30
$27.97
500 mg

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$104.00
1 g

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$195.00
5 g

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$824.00
25 g

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$2,100.00
50 g
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$3,520.00

About This Item

Empirical Formula (Hill Notation):
C35H53O2P
CAS Number:
Molecular Weight:
536.77
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
MDL number:

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Product Name

BrettPhos, 98%

Quality Segment

product line

Buchwald Ligand

assay

98%

form

solid

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Fluorinations

greener alternative product score

old score: 8
new score: 1
Find out more about DOZN™ Scoring

greener alternative product characteristics

Waste Prevention
Atom Economy
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

187-195 °C

functional group

phosphine

greener alternative category

SMILES string

COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1

InChI

1S/C35H53O2P/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28/h19-25,27-28H,9-18H2,1-8H3

InChI key

WDVGNXKCFBOKDF-UHFFFAOYSA-N

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 “Waste Prevention”, “Atom Economy” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Application

BrettPhos is a dialkylbiaryl phosphine ligand developed by the Buchwald group. It promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems.
It can be used in:
  • palladium-catalyzed trifluoromethylation of aryl chlorides
  • Buchwald-Hartwig amination
  • synthesis of 4-aryl and alkyl substituted, N6-alkylated pyridazine-3,6-diamines via a Buchwald protocol
For small scale and high throughput uses, product is also available as ChemBeads (928348)

Features and Benefits

  • White crystalline solid
  • Air- and moisture-stable
  • Thermally stable
  • Highly efficient
  • Wide functional group tolerance
  • Excellent selectivity and conversion


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This Item
663131638064638080
description

98%

description

98%

description

98%

description

98%

assay

98%

assay

98%

assay

98%

assay

98%

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Fluorinations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-C Bond Formation, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Hiyama Coupling, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

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: Carboxylations, reagent type: ligand
reaction type: Decarboxylations

form

solid

form

solid

form

-

form

solid

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

300

Quality Level

300

Quality Level

200

Quality Level

300

mp

187-195 °C

mp

123-126 °C

mp

187-190 °C (lit.)

mp

148-151 °C (lit.)


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Storage Class

11 - Combustible Solids

wgk

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable



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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

      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

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