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53199-31-8

53199-31-8 Structure

53199-31-8 Structure
IdentificationMore
[Name]

Bis(tri-tert-butylphosphine)palladium(0)
[CAS]

53199-31-8
[Synonyms]

BIS(TRI-T-BUTYLPHOSPHINE)PALLADIUM(0)
BIS(TRI-TERT-BUTYLPHOSPHINE)PALLADIUM
BIS(TRI-TERT-BUTYLPHOSPHINE)PALLADIUM (0)
Bis(tri-t-butylphosphine)palladium,
Bis(tri-tert-butylphosphin)palladium(0)
Bis(tri-t-butylphosphine)palladium(0),98%
Bis(tri-t-butyl)phosphino Pd0
Bis(tri-tert-butylphosphine)palladium(0), Pd 20.9%
Bis(tri-tert-butylphosphine)palladium (0) Reasonably stable for packaging and transfer.
Bis(tri-tert-butylphosphine)palladium (0), (Pd-116) Ampouled under argon
[EINECS(EC#)]

640-284-9
[Molecular Formula]

C24H54P2Pd
[MDL Number]

MFCD03094580
[Molecular Weight]

511.05
[MOL File]

53199-31-8.mol
Questions And AnswerBack Directory
[Synthesis]

In a dry reaction flask, [Pd(allyl)Cl]₂ (1.91 g, 5.2 mmol) was dissolved in a dry acetonitrile solution (350 mL). Then, in a nitrogen-filled glove box, tri-tert-butylphosphine (6.54 g) was added to the palladium complex in one go. After stirring the reaction mixture for a period of time, a turbid yellow solution formed. Within a few minutes, the reaction mixture slowly became opaque. Stirring the reaction mixture for another 18 h yielded a milky white mixture. After the reaction was complete, the crude reaction mixture was filtered through a medium-sized filter, and the solid product was collected. The solid was washed with acetonitrile (3 × 50 mL) and dried under vacuum to obtain di(tri-tert-butylphosphine)palladium.

Synthetic Route of Bis(tri-tert-butylphosphine)palladium(0)

Figure 2. Synthetic Route of Bis(tri-tert-butylphosphine)palladium(0)

[Reaction]

  1. Introduced as an easier to handle Pd/P(t-Bu)3-based catalyst for the Negishi cross-coupling of aryl/vinyl chlorides.
  2. A versatile catalyst for the cross-coupling of aryl and vinyl chlorides.
  3. Catalyst for the amination of aryl chlorides and bromides using aqueous hydroxide bases.
  4. Useful catalyst for the cross-coupling of heteroaromatic carboxylic acids.
  5. Pd-catalyzed Newnan-Kwart rearrangement of O-aryl thiocarbamates.
  6. Cross-coupling of silanolates and halides.
  7. Elimination/isomerization of enol triflates derived from β-ketoesters.
 Reactions of 53199-31-8
Chemical PropertiesBack Directory
[Appearance]

Off white crystalline solid
[Melting point ]

>300 °C
[storage temp. ]

Freezer
[form ]

Crystals
[color ]

Off-white to orange-brown
[Water Solubility ]

insoluble
[Sensitive ]

Light, Air & Moisture Sensitive
[InChI]

InChI=1S/2C12H27P.Pd/c2*1-10(2,3)13(11(4,5)6)12(7,8)9;/h2*1-9H3;/q;;-2/p+2
[InChIKey]

XULQKWNZCKOVSU-UHFFFAOYSA-P
[SMILES]

P(C(C)(C)C)(C(C)(C)C)(C(C)(C)C)[Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C
[CAS DataBase Reference]

53199-31-8(CAS DataBase Reference)
[Storage Precautions]

Store under nitrogen
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
[TSCA ]

No
[HS Code ]

28439000
[Storage Class]

11 - Combustible Solids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Tetrahydrofuran-->Toluene-->Acetonitrile-->Magnesium-->Phosphorus trichloride-->Hydrazine hydrate-->Palladium chloride-->2-Chloro-2-methylpropane
Hazard InformationBack Directory
[Chemical Properties]

Off white crystalline solid
[Uses]

Catalyst for Suzuki coupling on a multisubstituted sp 3 -carbon (eq. 1) Catalyst for Stille coupling reaction of aryl chlorides 2 (eq. 2) Catalyst for Negishi coupling reaction 3 (eq. 3) Catalyst for Heck coupling to form tetrasubstituted olefins 4 (eq. 4) Catalyst for Buchwald-Hartwig amination of aryl halide 5 (eq. 5) Catalyst for carbonylation of aryl halides with carbamoylsilanes 6 (eq. 6) t -Bu 3 P) 2 catalyst.
[General Description]

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.
[reaction suitability]

core: palladium
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: catalyst
Spectrum DetailBack Directory
[Spectrum Detail]

Bis(tri-tert-butylphosphine)palladium(0)(53199-31-8)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Bis(tri-tert-butylphosphine)palladium(0), 98%(53199-31-8)
[Alfa Aesar]

Bis(tri-tert-butylphosphine)palladium(0), Pd 20.9%(53199-31-8)
[Sigma Aldrich]

53199-31-8(sigmaaldrich)
[TCI AMERICA]

Bis(tri-tert-butylphosphine)palladium(0),>98.0%(T)(53199-31-8)
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