MilliporeSigma
All Photos(8)

741825

Sigma-Aldrich

XPhos Pd G2

98%

Sign Into View Organizational & Contract Pricing

Select a Size

Synonym(s):
2nd Generation XPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), X-Phos aminobiphenyl palladium chloride precatalyst, XPhos-Pd-G2
Empirical Formula (Hill Notation):
C45H59ClNPPd
CAS Number:
Molecular Weight:
786.80
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

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

202-210 °C

functional group

phosphine

SMILES string

Nc1ccccc1-c2ccccc2[Pd]Cl.Nc3ccccc3-c4ccccc4[Pd]Cl.CC(C)c5cc(C(C)C)c(-c6cccc(c6)P(C7CCCCC7)C8CCCCC8)c(c5)C(C)C.CC(C)c9cc(C(C)C)c(c(c9)C(C)C)-c%10ccccc%10P(C%11CCCCC%11)C%12CCCCC%12

InChI

1S/2C33H49P.2C12H10N.2ClH.2Pd/c1-23(2)27-21-31(24(3)4)33(32(22-27)25(5)6)26-14-13-19-30(20-26)34(28-15-9-7-10-16-28)29-17-11-8-12-18-29;1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28;2*13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;;;/h13-14,19-25,28-29H,7-12,15-18H2,1-6H3;13-14,19-25,27-28H,7-12,15-18H2,1-6H3;2*1-6,8-9H,13H2;2*1H;;/q;;;;;;2*+1/p-2

InChI key

HMRJFNBZAWHTGN-UHFFFAOYSA-L

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
763381753009704954
XPhos Pd G2 98%

Sigma-Aldrich

741825

XPhos Pd G2

XPhos Pd G3 98%, 1:1 MTBE adduct

Sigma-Aldrich

763381

XPhos Pd G3

SPhos Pd G2

Sigma-Aldrich

753009

SPhos Pd G2

XPhos Pd G1

Sigma-Aldrich

704954

XPhos Pd G1

form

solid

form

solid

form

solid

form

solid

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

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

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

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

202-210 °C

mp

146-151 °C (decomposition)

mp

218 °C (dec.)

mp

205-210 °C

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

XPhos Pd G2 is a bulky monodentate biaryl ligand. It is a Buchwald′s 2nd generation preformed catalyst. It undergoes rapid reductive elimination to form a reactive, monoligated Pd(0) species.

Application

2nd Generation Buchwald Precatalysts

  • Widely used for Suzuki-Miyaura cross-coupling reactions
XPhos Pd G2 was employed as catalyst in the following reactions:
  • Palladium-catalyzed Suzuki-Miyaura coupling reactions of potassium organotrifluoroborates and sulfamates.
  • Suzuki-Miyaura cross-coupling reactions of sensitive aryl and heteroarylboronic acids.
  • Synthesis of potassium Boc-protected secondary aminomethyltrifluoroborates, via Suzuki-Miyaura cross-coupling reaction.
For small scale and high throughput uses, product is also available as ChemBeads (927775)

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 8

1 of 8

Gary A Molander et al.
Organic letters, 14(17), 4458-4461 (2012-08-31)
Seven potassium Boc-protected secondary aminomethyltrifluoroborates were prepared in a standardized two-step process. The Suzuki-Miyaura cross-coupling reaction was studied with this new class of nucleophiles, and a large variety of aryl and hetaryl chlorides provided the desired products in good to
Gary A Molander et al.
Organic letters, 15(10), 2534-2537 (2013-05-08)
Sulfamates were studied as the electrophilic partners in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with potassium Boc-protected primary and secondary aminomethyltrifluoroborates. A broad range of substrates was successfully coupled to provide the desired products. Complex molecules containing a new carbon-carbon bond
Gary A Molander et al.
The Journal of organic chemistry, 78(8), 4123-4131 (2013-04-11)
A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not

Related Content

Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service