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753009

SPhos Pd G2

solid

Synonym(s):

2nd Generation SPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), SPhos-Pd-G2

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Size/SKUAvailabilityPrice
250 mg
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$72.20
1 g
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$197.00
5 g
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$627.00
$470.25

About This Item

Empirical Formula (Hill Notation):
C38H45ClNO2PPd
CAS Number:
Molecular Weight:
720.62
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22
MDL number:

$72.20


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Product Name

SPhos Pd G2,

Quality Segment

product line

Buchwald precatalyst Generation 2

form

solid

feature

generation 2

reaction suitability

core: palladium, 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

mp

218 °C (dec.)

functional group

phosphine

SMILES string

COC1=CC=CC(OC)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2.NC5=C(C6=C([Pd]Cl)C=CC=C6)C=CC=C5

InChI

1S/C26H35O2P.C12H10N.ClH.Pd/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;/h9-11,16-21H,3-8,12-15H2,1-2H3;1-6,8-9H,13H2;1H;/q;;;+1/p-1

InChI key

NOMWEFBAPVZIIP-UHFFFAOYSA-M

General description

SPhos Pd G2 is a second generation (G2) precatalyst in which phenethylamine based backbone of the (G1) complex is substituted with a biphenyl-based ligand. This improvement on the previous generation allows creating the active palladium species at room temperature with weak phosphate or carbonate bases. The catalyst proves remarkably adept at achieving a variety of Suzuki-Miyaura couplings among other cross-coupling reactions.

Application

Application in Suzuki-Miyaura coupling:
  • Self-arylation of 1-alkyl-3-bromo-2-phenyl-2,1-borazaronaphthalenes to form 2,1-borazaronaphthols.
  • Suzuki–Miyaura coupling of [Ru(bpy)2]+ with 4-carboxyphenylboronic acid.
  • Suzuki–Miyaura coupling of β-borylated porphyrins with 2-iodoaniline.


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763012741825763004
description

-

description

95%

description

98%

description

95%

reaction suitability

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

reaction suitability

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

reaction suitability

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

reaction suitability

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

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

218 °C (dec.)

mp

152-163 °C (decomposition)

mp

202-210 °C

mp

176-178 °C (decomposition)

product line

Buchwald precatalyst Generation 2

product line

Buchwald precatalyst Generation 2

product line

Buchwald precatalyst Generation 2

product line

Buchwald precatalyst Generation 3

feature

generation 2

feature

generation 2

feature

generation 2

feature

generation 3


Storage Class

11 - Combustible Solids

WGK

WGK 3

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

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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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