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tBuXPhos

Name: <I>t</I>BuXPhos
Brand: ALDRICH
Price: 48.3 USD
Availability: InStock

98%, solid

Synonym(s):

tBuXPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, t-Bu XPhos, tert-Butyl XPhos

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Pack Size	Availability	Price
1 g	Available to ship TODAYfromMILWAUKEE	$64.40 $48.30
5 g	Available to ship TODAYfromMILWAUKEE	$203.00 $172.55
25 g	Available to ship TODAYfromMILWAUKEE	$961.00
100 g	Available to ship TODAYfromMILWAUKEE	$1,750.00 $1,312.50
500 g	Check Cart for Availability	$8,070.00

About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₅P

CAS Number:

564483-19-8

Molecular Weight:

424.64

UNSPSC Code:

12352002

PubChem Substance ID:

24882908

NACRES:

NA.22

MDL number:

MFCD06411306

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Properties

Product Name

tBuXPhos, 98%

Quality Level

300

product line

Buchwald Ligand

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: Carboxylations, reagent type: ligand
reaction type: Decarboxylations

greener alternative product score

old score: 12
new score: 1
Find out more about DOZN™ Scoring

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

mp

148-151 °C (lit.)

functional group

phosphine

greener alternative category

Re-engineered,

SMILES string

CC(P(C(C=CC=C1)=C1C(C(C(C)C)=CC(C(C)C)=C2)=C2C(C)C)C(C)(C)C)(C)C

InChI

1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3

InChI key

SACNIGZYDTUHKB-UHFFFAOYSA-N

Description

General description

tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

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”, “Use of Renewable Feedstock” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Learn more about Buchwald Phosphine Ligands

Application

tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.
It can be used in the following reactions:

Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.

tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr₄F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.

Legal Information

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

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1 of 1

This Item	901904	936693	638072
Sigma-Aldrich 638080 tBuXPhos	Sigma-Aldrich 901904 tBuXPhos	Sigma-Aldrich 936693 tBuXPhos ChemBeads	Sigma-Aldrich 638072 SPhos
reaction suitability reaction type: Cross Couplings, reagent type: ligand reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand reaction type: Decarboxylations, reagent type: ligand reaction type: Arylations, reagent type: ligand reaction type: Carboxylations	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, reagent type: ligand	reaction suitability -	reaction suitability reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, 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: ligand reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand reaction type: Heck Reaction, reagent type: ligand reaction type: Kumada Coupling, reagent type: ligand reaction type: Negishi Coupling, reagent type: ligand reaction type: Suzuki-Miyaura Coupling
assay 98%	assay 95%	assay -	assay 98%
form solid	form powder or crystals	form solid	form -
functional group phosphine	functional group phosphine	functional group -	functional group phosphine
Quality Level 300	Quality Level -	Quality Level 100	Quality Level 300
mp 148-151 °C (lit.)	mp 148-151 °C (lit.), 150 °C	mp -	mp 164-166 °C (lit.)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000431637

0000424533

0000419594

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Articles

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald Phosphine Ligands

Global Trade Item Number

SKU	GTIN
638080-5G	04061832726496
638080-25G	04061833548622
638080-100G	04061833301531
638080-1G	04061832726489
638080-500G	04061833499528

Questions

1–2 of 2 Questions

Anonymous

10 months ago

How can I determine the shelf life / expiration / retest date of this product?

1 answer
1. Technical Support
  
  10 months ago
  
  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?
Anonymous

a year ago

How is shipping temperature determined? And how is it related to the product storage temperature?

1 answer
1. Technical Support
  
  a year ago
  
  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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