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570958

Sigma-Aldrich

Tri-tert-butylphosphine

98%

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Synonym(s):
P(t-Bu)3
Linear Formula:
[(CH3)3C]3P
CAS Number:
Molecular Weight:
202.32
Beilstein/REAXYS Number:
1738613
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

reaction suitability

reaction type: Cross Couplings
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

bp

102-103 °C/13 mmHg (lit.)

mp

30-35 °C (lit.)

density

0.834 g/mL at 20 °C (lit.)

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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Tri-tert-butylphosphine 98%

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Tri-tert-butylphosphine solution 1.0 M in toluene

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Tri-tert-butylphosphine solution

Tri-tert-butylphosphine solution 1.0 M in 2-methyltetrahydrofuran

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Tri-tert-butylphosphine solution

assay

98%

assay

-

assay

-

assay

-

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

bp

102-103 °C/13 mmHg (lit.)

bp

-

bp

-

bp

-

mp

30-35 °C (lit.)

mp

-

mp

-

mp

-

density

0.834 g/mL at 20 °C (lit.)

density

0.878 g/mL

density

0.861 g/mL at 25 °C

density

0.853 g/mL

Application

Preferred ligand in the palladium-catalyzed coupling of arylboronic acids with phenyliodonium ylides of hydroxyquinones. Also used with Pd2(dba)3 for the α-arylation of trimethylsilyl enol ethers with aryl halides.

pictograms

FlameCorrosion

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Pyr. Sol. 1 - Skin Corr. 1B

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

1.4 °F

flash_point_c

-17 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Tetsuo Iwama et al.
Organic letters, 8(25), 5725-5728 (2006-12-01)
Inter- and intramolecular arylations of trimethylsilyl enol ethers with aryl halides are accomplished regiospecifically in the presence of a palladium catalyst and tributyltin fluoride in refluxing benzene or toluene. The optimal catalyst system called for the use of Pd2(dba)3 and
Synlett, 2597-2597 (2006)
Maria V Zakharova et al.
ACS applied materials & interfaces, 10(15), 13199-13210 (2018-03-10)
Conventional amines and phosphines, such as diethylenetriamine, diphenylpropylphosphine, triethylamine, and tetramethylpiperidine, were grafted or impregnated on the surface of metalated SBA-15 materials, such as Ti-, Al-, and Zr-SBA-15, to generate air-stable solid-supported Lewis acid-base pairs. The Lewis acidity of the

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