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CAS RN: 3375-31-3 | Product Number: P2161

Palladium(II) Acetate (Purified)


Purity: >98.0%(T)
Chemical Substance Law (ENCS):   2-693
Synonyms:
  • Acetic Acid Palladium(II) Salt (Purified)
Documents:
1G
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Product Number P2161
Purity / Analysis Method >98.0%(T)
Molecular Formula / Molecular Weight C__4H__6O__4Pd = 224.51  
Physical State (20 deg.C) Solid
Packaging and Container 1G-Glass Bottle with Plastic Insert (View image)
CAS RN 3375-31-3
Reaxys Registry Number 3375313
PubChem Substance ID 253662088
SDBS (AIST Spectral DB) 12841
Merck Index (14) 6991
MDL Number

MFCD00012453

Specifications
Appearance Light yellow to Brown powder to crystal
Purity(Chelometric Titration) min. 98.0 %
Elemental analysis(Nitrogen) max. 0.30 %
Properties (reference)
Maximum Absorption Wavelength 400(EtOH) nm
Solubility (soluble in) Acetone
GHS
Pictogram Pictogram
Signal Word Danger
Hazard Statements H318 : Causes serious eye damage.
Precautionary Statements P280 : Wear eye protection/ face protection.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
Related Laws:
Chemical Substance Law (ENCS) 2-693
RTECS# AJ1900000
Transport Information:
Application
TCI Practical Example: Miyaura-Ishiyama Borylation using Pd(OAc)2

Used Chemicals

Procedure

To the solution of 3-iodobenzalehyde (1.16 g, 5.00 mmol) in dry DMF (15.0 mL) were added potassium acetate (981 mg, 10.0 mmol), palladium(II) acetate (112 mg, 0.500 mmol, 10 mol%) and bis(pinacolato)diborane (1.27 g, 5.00 mmol). The reaction mixture was stirred at 80 ºC for 7 h. The reaction mixture was cooled to room temperature and quenched with H2O (15 mL) and saturated NH4Cl aq. (10 mL), then the mixture was extracted twice with hexane : EtOAc = 4 : 1. The combined organic layer was washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated under reduced pressure to afford the crude product as a yellow oil. The crude product was purified by column chromatography on silica-gel (hexane → hexane : EtOAc = 1:1) to afford 3-formylphenylboronic acid pinacol ester as a yellow oil (500 mg, 2.15 mmol, 43%).

Experimenter's Comments

(1) DMF was dried over molecular sieves.

(2) Completion of the reaction was confirmed by TLC (hexane : EtOAc = 1 : 1, Rf = 0.30) and GC.

Analytical Data(3-Formylphenylboronic Acid Pinacol Ester)

1H NMR (400 MHz, CDCl3); δ 10.1 (s, 1H), 8.30 (s, 1H), 8.06 (d, J = 4.0 Hz, 1H), 7.99 (ddd, J = 1.6, 1.8, 7.8 Hz, 1H), 7.53 (t, J = 8.0 Hz, 1H), 1.37 (s, 12H).

Lead Reference


Application
TCI Practical Example: Pd(OAc)2-catalyzed Heck Reaction

Used Chemicals

Procedure

To a solution of 4-bromophenol (1.5 g, 8.7 mmol) in triethylamine (10 mL), styrene (1.1 g, 10.8 mmol), tri(o-tolyl)phosphine (0.16 g, 0.52 mmol) and palladium(II) acetate (0.020 g, 0.087 mmol) were successively added at room temperature. The reaction mixture was stirred overnight at 100 °C under nitrogen atmosphere. To a 1 mol/L HCl aq. (100 mL) the reaction mixture was added below 15 °C. Then diethyl ether (100 mL) was added and the mixture was stirred for 10 min. The solution was partitioned and the water phase was extracted by diethyl ether (50 mL). Then combined organic layer was dried over sodium sulfate and filtered. The residue was recrystallized from toluene giving trans-4-hydroxystilbene as a pale brown solid (0.97 g, 57% yield).

Experimenter's Comments

The reaction mixture was monitored by 1H NMR.

Analytical Data(trans-4-Hydroxystilbene)

1H NMR (400 MHz, CDCl3); δ 9.59 (s, 1H), 7.53 (d, J = 7.3 Hz, 2H), 7.42 (d, J = 8.2 Hz, 2H), 7.34 (dd, J = 7.8, 7.3 Hz, 2H), 7.22 (t, J = 7.3 Hz, 1H), 7.15 (d, J = 16.5 Hz, 1H), 7.01 (d, J = 16.5 Hz, 1H), 6.77 (d, J = 8.7 Hz, 2H).

13C NMR (101 MHz, CDCl3); δ 157.3, 137.6, 128.7 (2 C), 128.5, 128.1, 127.9 (2 C), 127.0, 126.1 (2 C), 125.1, 115.6 (2 C).

Lead Reference

Other References


Application
TCI Practical Example: Buchwald-Hartwig Amination Using Pd(OAc)2

Used Chemicals

Procedure

To a solution of sodium tert-butoxide (0.54 g, 5.6 mmol), palladium(II) acetate (4.5 mg, 0.020 mmol), and JohnPhos (0.012 g, 0.040 mmol) in toluene (8 mL) 4-chlorotoluene (0.51 g, 4.0 mmol) and morpholine (0.42 g, 4.8 mmol) were successively added at room temperature. The mixture was stirred under nitrogen atmosphere at room temperature for 1.5 days, then under reflux condition for 0.5 days. Diethyl ether (20 mL) was added to the reaction mixture and filtered through celite. Solvent was removed and the residue was purified by column chromatography (1:4 ethyl acetate / hexane on SiO2), giving 4-(p-tolyl)morpholine as a pale brown solid (0.45 g, 63% yield).

Experimenter's Comments

The reaction mixture was monitored by 1H NMR.

Analytical Data (4-(p-Tolyl)morpholine)

1H NMR (400 MHz, CDCl3); δ 7.10 (d, J = 8.2 Hz, 2H), 6.85 (d, J = 8.2 Hz, 2H), 3.87 (t, J = 4.6 Hz, 4H), 3.12 (t, J = 4.8 Hz, 4H), 2.28 (s, 3H).

13C NMR (101 MHz, CDCl3); δ 129.9 (4 C), 116.2 (2 C), 67.1 (2 C), 50.1 (2 C), 20.6.

Lead Reference

Other References


Application
TCI Practical Example: Stille Coupling using Pd(OAc)2 and Xphos

Used Chemicals

Procedure

To a solution of palladium(II) acetate (44.9 mg, 0.200 mmol, 4 mol%), XPhos (143 mg, 0.300 mmol, 6 mol%), cesium fluoride (2.28 g, 15.0 mmol) and 2-chlorophenothiazine (1.17 g, 5.00 mmol) in toluene (15.0 mL) was added tributyl(2-thienyl)tin (2.24 g, 1.90 mL, 6.00 mmol) and the reaction solution was stirred at 80 ºC for 24 h. After reaction mixture was cooled to room temperature, dichloromethane (15 mL) and H2O (15 mL) were added. Separated water phase was extracted with dichloromethane (15 mL) for 3 times. Combined organic layer was dried over MgSO4 (10 g) and concentrated under reduced pressure to afford the crude product as a brown solid. Crude was purified by column chromatography on silica-gel (hexane: EtOAc = 50 : 1 ~ 5 : 1 → dichloromethane) to afford 2-(thiophen-2-yl)-10H-phenothiazine as a yellow solid (990 mg, 3.51 mmol, 70%).

Experimenter's Comments

Completion of the reaction was confirmed by TLC (Hexane:EtOAc = 10:1, Rf: S.M.=0.28 T.M.=0.18) and GC.

Analytical Data(2-(Thiophen-2-yl)-10H-phenothiazine)

1H NMR (400 MHz, CDCl3); δ 7.92 (brs, 1H), 7.42 (dd, J = 0.9, 5.0 Hz, 1H), 7.35 (dd, J = 0.9, 3.6 Hz, 1H), 7.08-7.13 (m, 2H), 6.94-7.03 (m, 4H), 6.73-6.82 (m, 2H).

Lead Reference


Application
Dynamic Kinetic Resolution using a Palladium / QuinoxP* Complex

References


PubMed Literature


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