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CAS RN: 32005-36-0 | Product Number: B1374

Bis(dibenzylideneacetone)palladium(0)


Purity:
Synonyms:
  • Palladium(0) Bis(dibenzylideneacetone)
  • Bis(dba)palladium(0)
  • Pd(dba)2
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Product Number B1374
Molecular Formula / Molecular Weight C__3__4H__2__8O__2Pd = 575.02  
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive
CAS RN 32005-36-0
PubChem Substance ID 87564299
SDBS (AIST Spectral DB) 50493
MDL Number

MFCD00051942

Specifications
Appearance Red to Dark blue to Black powder to crystal
Content (Palladium) 18.0 to 24.0 %
Properties (reference)
Melting Point 150 °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.
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: Buchwald-Hartwig amination using a palladium catalyst and an alkylphosphine ligand

Used Chemicals

Procedure

Aniline (1.0 g, 10.7 mmol) and 4-chlorotoluene (1.4 g, 11.8 mmol) were dissolved in degassed toluene (10 mL) under nitrogen atmosphere. To this solution was added sodium tert-butoxide (1.54 g, 16.1 mmol), tri-tert-butylphosphonium tetrafluoroborate (31.1 mg, 0.1 mmol) and Pd(dba)2 (61.7 mg, 0.1 mmol, 1.5mol%). The reaction mixture was refluxed for 24 h and cooled to room temperature and quenched with H2O (10 mL). The organic phase was separated and washed with brine (10 mL), dried over MgSO4 (10 g), concentrated under reduced pressure to afford the crude product as a brown liquid. The crude product was purified by column chromatography on silica-gel (hexane : ethyl acetate = 95 : 5) to afford the desired product as a pale yellow crystalline solid (1.21 g, 6.6 mmol, 62%).

Experimenter’s Comments

Toluene was degassed by bubbling with N2 gas for 30 min.
The reaction mixture was analyzed by TLC (hexane : ethyl acetate = 1 : 1, Rf = 0.30) and GC.

Analytical Data (4-Methyl-N-phenylaniline)

1H NMR (400 MHz, CDCl3); δ 7.24-7.20 (t, J = 8.7 Hz, 3H), 7.07 (d, J = 8.7 Hz, 2H), 7.00-6.88 (m, 4H), 6.88-6.84 (m, 1H), 5.58 (s, 1H), 2.29 (s, 3H).

Lead Reference


Application
TCI Practical Example: Suzuki-Miyaura cross-coupling Using a Palladium Catalyst and SPhos

Used Chemicals

Procedure

To a 3-necked flask was charged with bis(dibenzylideneacetone)palladium (0) (66 mg, 0.115 mmol, 1.5 mol%), SPhos (94 mg, 0.229 mmol, 3.0 mol%), 2-methylphenylboronic acid (1.56 g, 11.5 mmol, 1.5 equiv.), tripotassium phosphate (4.87 g, 22.9 mmol, 3.0 equiv.) degassed toluene (15 mL), and ion-exchange water (1.5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 2-Chloro-m-xylene (1.0 mL, 7.64 mmol, 1.0 equiv.) was added one portion. The resulting mixture was stirred at reflux for 7 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane only) to afford the corresponding compound as a colorless oil (1.46 g, 97%).

Experimenter's Comments

i) Toluene was degassed by bubbling with nitrogen gas for 30 min.
ii) The reaction mixture was monitored by GC.

Analytical Data(2,2',6-Trimethyl-1,1'-biphenyl)

1H NMR (400 MHz, CDCl3); δ 7.23-7.33 (m, 3H), 7.22-7.10 (m, 3H), 7.00-7.06 (m, 1H), 1.99 (s, 3H), 1.97 (s, 6H).

13C NMR (101 MHz, CDCl3); δ 141.0, 140.5, 135.8, 135.5, 129.9, 128.8, 127.2 127.0, 126.9, 126.0, 20.3, 19.4.

Lead Reference


Application
TCI Practical Example: Buchwald-Hartwig Amination

Used Chemicals

Procedure

To a 2-necked flask was charged with bis(dibenzylideneacetone)palladium (0) (36 mg, 0.0633 mmol, 1.5 mol%), XPhos (60 mg, 0.127 mmol, 3.0 mol%), sodium tert-butoxide (811 mg, 8.44 mmol, 2.0 equiv.) and toluene (5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 4-chlorotoluene (0.5 mL, 4.22 mmol, 1.0 equiv.), and morpholine (0.55 mL, 6.33 mmol, 1.5 equiv.) were added in one portion. The resulting mixture was stirred at reflux for 6 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane : ethyl acetate = 9 : 1) to afford the corresponding compound as an orange solid (700 mg, 94%).

Experimenter's Comments

Toluene was degassed by bubbling with nitrogen gas for 30 min.
The reaction mixture was monitored by GC.

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 7.10 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H), 3.87 (t, J = 4.8 Hz, 4H), 3.11 (t, J = 4.8 Hz, 4H), 2.28 (s, 3H).

13C NMR (101 MHz, CDCl3); δ 149.1, 129.7, 129.5, 116.0, 66.9, 49.9, 20.4.

Lead Reference


Application
Kumada-Corriu Cross-Coupling Reaction

References


PubMed Literature


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