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655325

Sigma-Aldrich

Tri-tert-butylphosphine solution

1.0 M in toluene

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Synonym(s):
P(t-Bu)3, P(t-Bu)3
Empirical Formula (Hill Notation):
C12H27P
CAS Number:
Molecular Weight:
202.32
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reagent type: ligand
reaction type: Addition Reactions

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Heck Reaction

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

concentration

1.0 M in toluene

density

0.861 g/mL at 25 °C

functional group

phosphine

SMILES string

CC(C)(C)P(C(C)(C)C)C(C)(C)C

InChI

1S/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3

InChI key

BWHDROKFUHTORW-UHFFFAOYSA-N

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1 of 4

This Item
247049T49484901441
vibrant-m

655325

Tri-tert-butylphosphine solution

vibrant-m

247049

Tributylphosphine

vibrant-m

T49484

Tri-n-butylphosphine

vibrant-m

901441

Tri-tert-butylphosphine solution

reaction suitability

reagent type: ligand
reaction type: Addition Reactions, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Negishi Coupling

reaction suitability

-

reaction suitability

reagent type: ligand
reaction type: Acetylations, reagent type: ligand
reaction type: Addition Reactions, reagent type: ligand
reaction type: Stille Coupling

reaction suitability

reagent type: ligand
reaction type: Addition Reactions, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Heck Reaction, 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

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

density

0.861 g/mL at 25 °C

density

0.81 g/mL at 25 °C (lit.)

density

0.81 g/mL at 25 °C (lit.)

density

0.853 g/mL

concentration

1.0 M in toluene

concentration

-

concentration

-

concentration

1.0 M in 2-methyltetrahydrofuran

Application

Tri-tert-butylphosphine is a suitable ligand for palladium-catalyzed coupling reactions such as:
  • Heck Reactions
  • Negishi cross-coupling
  • Stille reactions
  • Sonogashira reactions

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

39.9 °F

flash_point_c

4.4 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Pd (PhCN) 2Cl2/P (t-Bu) 3: a versatile catalyst for Sonogashira reactions of aryl bromides at room temperature.
Hundertmark T, et al.
Organic Letters, 2(12), 1729-1731 (2000)
Pd/P (t-Bu) 3: a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides
Littke A F, et al.
Journal of the American Chemical Society, 124(22), 6343-6348 (2002)
Heck reactions in the presence of P (t-Bu) 3: Expanded scope and milder reaction conditions for the coupling of aryl chlorides.
Littke A F, et al.
The Journal of Organic Chemistry, 64(1), 10-11 (1999)
The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd (P (t-Bu) 3) 2 as a catalyst
Dai C, et al.
Journal of the American Chemical Society, 123(12), 2719-2724 (2001)
Gregory C Fu
Accounts of chemical research, 41(11), 1555-1564 (2008-10-25)
Metal-catalyzed coupling reactions of aryl electrophiles with organometallics and with olefins serve as unusually effective tools for forming new carbon-carbon bonds. By 1998, researchers had developed catalysts that achieved reactions of aryl iodides, bromides, and triflates. Nevertheless, many noteworthy challenges

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