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638080

Sigma-Aldrich

tBuXPhos

greener alternative

98%

Synonym(s):

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

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250 MG
CN¥3,252.96
1 G
CN¥1,979.51

CN¥3,252.96

Estimated to ship onApril 07, 2025Details

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250 MG
CN¥3,252.96
1 G
CN¥1,979.51

About This Item

Empirical Formula (Hill Notation):
C29H45P
CAS Number:
564483-19-8
Molecular Weight:
424.64
MDL number:
MFCD06411306
UNSPSC Code:
12352002
PubChem Substance ID:
24882908
NACRES:
NA.22

CN¥3,252.96

Estimated to ship onApril 07, 2025Details

Request a Bulk Order

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

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Show Differences

1 of 4

This Item
541435536512655201
Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] average Mn 40,000-70,000

541443

Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]

Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] average Mn 70,000-100,000

541435

Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]

Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]

536512

Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene]

Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) high-conductivity grade, 3.0-4.0% in H2O

655201

Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate)

description

Band gap: 2.3 eV

description

Band gap: 2.3 eV

description

Band gap: 2.3 eV

description

-

mol wt

average Mn 40,000-70,000

mol wt

average Mn 70,000-100,000

mol wt

-

mol wt

-

fluorescence

λex 493 nm; λem 554 nm in toluene

fluorescence

λex 495 nm; λem 554 nm in toluene

fluorescence

λex 493 nm; λem 554 nm in toluene

fluorescence

-

orbital energy

HOMO -5.3 eV 

orbital energy

HOMO -5.3 eV , LUMO -3 eV 

orbital energy

HOMO -5.3 eV , LUMO -3 eV 

orbital energy

-

OLED device performance

ITO/PEDOT:PSS/MEH-PPV/Al

  • Color: orange-red
  • Max. Luminance: 220 Cd/m2
  • Max. EQE: 0.3 %
  • Turn-On Voltage: 3.8 V

OLED device performance

ITO/PEDOT:PSS/MEH-PPV/Al

  • Color: orange-red
  • Max. Luminance: 220 Cd/m2
  • Max. EQE: 0.3 %
  • Turn-On Voltage: 3.8 V
, ITO/PEDOT:PSS/MEH-PPV/PBO/Al
  • Color: orange-red
  • Max. Luminance: 970 Cd/m2
  • Max. EQE: 1.9 %
  • Turn-On Voltage: 2.9 V
, ITO/PEDOT:PSS/MEH-PPV/PBZT/Al
  • Color: orange-red
  • Max. Luminance: 1400 Cd/m2
  • Max. EQE: 2.5 %
  • Turn-On Voltage: 2.8 V

OLED device performance

ITO/PEDOT:PSS/MEH-PPV/Al

  • Color: orange-red
  • Max. Luminance: 220 Cd/m2
  • Max. EQE: 0.3 %
  • Turn-On Voltage: 3.8 V
, ITO/PEDOT:PSS/MEH-PPV/PBO/Al
  • Color: orange-red
  • Max. Luminance: 970 Cd/m2
  • Max. EQE: 1.9 %
  • Turn-On Voltage: 2.9 V
, ITO/PEDOT:PSS/MEH-PPV/PBZT/Al
  • Color: orange-red
  • Max. Luminance: 1400 Cd/m2
  • Max. EQE: 2.5 %
  • Turn-On Voltage: 2.8 V

OLED device performance

-

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 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.[1]
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.[2]
  • Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.[3]
  • Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.[4]

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000431637
    0000431637
    0000424533
    0000424533
    0000419596

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    Arkaitz Correa et al.
    Journal of the American Chemical Society, 131(44), 15974-15975 (2009-11-06)
    A novel protocol for the direct carbon dioxide insertion (CO(2)) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO(2), there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and
    Palladium-catalyzed substitution and cross-coupling of benzylic fluorides.
    Blessley G, et al.
    Organic Letters, 14(11), 2754-2757 (2012)
    Palladium-Catalyzed C?N Cross Coupling of Sulfinamides and Aryl Halides.
    Sun X, et al.
    The Journal of Organic Chemistry, 77(9), 4454-4459 (2012)
    Intermolecular [2+ 2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold (I).
    de Orbe ME and Echavarren AM.
    Organic Syntheses, 93, 115-126 (2016)
    Palladium?Catalyzed Rapid Methoxylation and Deuteriomethoxylation of Bromo?chalcones: Uncovering the Catalytic Activity of the Pd/tBuXPhos Catalyst System.
    Rangarajan T M, et al.
    ChemistrySelect, 1(21), 6894-6901 (2016)
    View All Related Papers

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    Buchwald Phosphine Ligands

    Buchwald Phosphine Ligands

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

    Buchwald Phosphine Ligands

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

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