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CAS RN: 95464-05-4 | Product Number: B2064

[1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct


Purity: >98.0%(T)
Synonyms:
  • [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) Dichloromethane Adduct
  • Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) Dichloromethane Adduct
Documents:
1G
£55.00
5   ≥40 
5G
£185.00
5   ≥40 
25G
£600.00
8   ≥40 

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Product Number B2064
Purity / Analysis Method >98.0%(T)
Molecular Formula / Molecular Weight C__3__4H__2__8Cl__2FeP__2Pd·CH__2Cl__2 = 816.64 
Physical State (20 deg.C) Solid
CAS RN 95464-05-4
Reaxys Registry Number 13180458
PubChem Substance ID 87564938
MDL Number

MFCD00792899

Specifications
Appearance Light yellow to Amber to Dark green powder to crystal
Purity(Argentometric Titration) min. 98.0 %
Properties (reference)
Melting Point 280 °C
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H302 + H312 + H332 : Harmful if swallowed, in contact with skin or if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P261 : Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water. Call a POISON CENTER/doctor if you feel unwell.
P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
Related Laws:
Transport Information:
HS Number 2843909000
Application
TCI Practical Example: Suzuki-Miyaura Cross Coupling Using the Palladium-phosphinoferrocene Complex

Used Chemicals

Procedure

To a solution of 2-bromo-3-methylpyridine (103 mg, 60 mmol) in degassed toluene (0.6 mL, 0.1 mol/L) and H2O (0.2 mL) was added 3-(tert-butoxycarbonyl)phenylboronic acid (150 mg, 0.66 mmol, 1.1 equiv), K2CO3 (398 mg, 2.9 mmol, 4.8 equiv), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (24.5 mg, 3.0 μmol, 5.0 mol%) and the mixture was stirred at reflux for 4 h. The reaction mixture was diluted with H2O (10 mL) and extracted with EtOAc (20 mL x 3). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane : EtOAc = 1 : 0 to 4 : 1) to give 1 as a pale yellow oil (155 mg, 94%).

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane : EtOAc = 2 : 1, Rf = 0.62).

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 8.54 (brd, J = 5.0 Hz, 1H), 8.14 (q, J = 1.5 Hz, 1H), 8.03 (dt, J = 7.8, 1.4 Hz, 1H), 7.69 (dq, J = 7.6, 1.5 Hz, 1H), 7.60 (m, 1H), 7.51 (dt, J = 7.7, 1.1 Hz, 1H), 7.21 (dd, J = 7.8, 4.6 Hz, 1H), 2.36 (s, 3H), 1.58 (s, 9H).

Lead Reference


Application
Borylation of Triflate with Pinacolborane

Typical procedure: To a degassed solution of L-tyrosine triflate derivative (500 mg, 1.17 mmol) and NMM (0.129 mL, 1.17 mmol) in dioxane (5 mL) is added PdCl2(dppf).CH2Cl2 (4.8 mg, 0.0059 mmol) and pinacolborane (0.255 mL, 1.76 mmol) at room temperature. The reaction mixture is then stirred for 24 h at 80 ℃. After cooling to room temperature, the mixture is concentrated and directly purified by silica gel column chromatography (heptane : ethyl acetate = 3 : 1) to give the borylation product as a colorless viscous oil (445 mg, 94% yield).

References


PubMed Literature


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