3375-31-3

Basic information

• Product Name: Palladium (II) Acetate
• Synonyms: ACETIC ACID PALLADIUM(II) SALT;PALLADIUM ACETATE;PALLADIUM(+2)ACETATE;PALLADIUM DIACETATE;PALLADIUM(II) ACETATE;PALLADIUM(II) ACETATE IN IONIC LIQUID ON SILICA;PALLADIUM (II) ACETATE, TRIMER;PALLADIUM II ACETATE TRIMERIC ORANGE-BROWN
• CAS NO: 3375-31-3
• Molecular Formula: C₄H₆O₄Pd
• Molecular Weight: 224.51
• EINECS: 222-164-4
• Product Categories: Metal Compounds;blocks;Catalysts-Ligands;Pd (Palladium) Compounds;Transition Metal Complexes (Environmentally-friendly Oxidation);Catalysts for Organic Synthesis;Classes of Metal Compounds;Environmentally-friendly Oxidation;Homogeneous Catalysts;Metal Complexes;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysts;CHIRAL CHEMICALS;CatalystsCatalysis and Inorganic Chemistry;Palladium;Supported Pd Catalysts;Supported Reagents;Supported Synthesis;metal acetate salt;chemical reaction,pharm,electronic,materials;Inorganics;Pd
• Mol File: 3375-31-3.mol
• Article Data: 28

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 117.1 °C at 760 mmHg
• Flash Point: 40 °C
• Appearance: Red-brown/Various Forms In Red-(Powder/Flake/Crystalline/Beads)
• Vapor Pressure: 0.002Pa at 25℃
• Storage Temp.: Store at R.T.
• Solubility: Soluble as monomer in glacial acetic acid or as trimer in benzen
• Water Solubility: insoluble
• Sensitive: Hygroscopic
• Merck: 14,6991
• BRN: 6086766
• CAS DataBase Reference: Palladium (II) Acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Palladium (II) Acetate(3375-31-3)
• EPA Substance Registry System: Palladium (II) Acetate(3375-31-3)

Safety Data

• Hazard Codes: Xi,Xn,C
• Statements: 41-36/37/38-40-35
• Safety Statements: 26-39-36/37/39-45-36
• RIDADR: 3261
• WGK Germany: 2
• RTECS: AJ1900000
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 3375-31-3(Hazardous Substances Data)

Usage

Reactions

Efficient catalyst for the arylation of olefins (Heck reaction). Catalyst for cross-coupling reactions. Catalyst for C-H activation. Precatalyst for enantioselective decarboxylative protonation of allyl β-ketoesters.

Chemical Properties

brown needles

Uses

suzuki reaction

Uses

Palladium (II) Acetate Trimer is used in Suzuki-Miyaura cross-coupling reactions. It also serves to catalyze the chemoselective reduction of nitroarenes.

Uses

A catalyst for intramolecular coupling.

General Description

Palladium(II) acetate is a homogenous oxidation catalyst. It participates in the activation of alkenic and aromatic compounds towards oxidative inter- and intramolecular nucleophilic reactions. Crystals of palladium(II) acetate have a trimeric structure, having symmetry D3h. Each of the palladium atoms in the crystals are joined to the other two by double acetate bridges. Microencapsulation of palladium(II) acetate in polyurea affords polyurea-encapsulated palladium(II) acetate. It is a versatile heterogeneous catalyst for various phosphine-free cross-coupling reactions. It participates as catalyst in the Heck coupling reaction of pthalides with different alkenes.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of palladium.

Purification Methods

It recrystallises from CHCl3 as purple crystals. It can be washed with AcOH and H2O and dried in air. Large crystals are obtained by dissolving it in *C6H6, adding half its volume of AcOH and allowing it to evaporate slowly at room temperature. It forms green adducts with nitrogen donors, it dissolves in KI solution to form solid PdI2 and a red solution of PdI42-, but is insoluble in aqueous saturated NaCl, and NaOAc. It dissolves in HCl to form PdCl42-. It is soluble in CHCl3, CH2Cl2, Me2CO, MeCN, Et2O, but it is insoluble in H2O, and decomposes when warmed in alcohols in which it is also insoluble. [Morehouse et al. Chem Ind (London) 544 1964, Stephenson et al. J Chem Soc 3632 1965, Skapski & Smart J Chem Soc (D) 658 1970, Heck Acc Chem Res 12 146 1979.]

InChI:InChI=1/2C2H4O2.Pd/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2

Synthetic route

palladium (7440-05-3) + acetic acid (64-19-7) → palladium diacetate (3375-31-3)

Conditions	Yield
With nitric acid In nitric acid; acetic acid boiling Pd-sponge in mixt. of glacial AcOH and concd. HNO3 (100:3 v/v), addn. of further Pd to end of evolution of N-oxides (if necessary); hot filtration, cooling (crystn.), washing (AcOH, water), drying in air;	99%
With nitric acid for 0.5h; Reflux;	92%
With nitric acid In acetic acid Pd oxidized with HNO3 in CH3COOH for 30 h according to Stephenson, T.A.,Morehouse, S.M., Powell, A.R., Heffer, J.P., and Wilkinson, G., J. Chem . Soc., 1965, vol. 6, no. 6, p. 3632; crystd.;	80%

[bis(acetoxy)iodo]benzene (3240-34-4) + palladium(II) iodide → palladium diacetate (3375-31-3)

Conditions	Yield
With iodine In dichloromethane mixt. of PdI2, PhI(OAc)2 and I2 in CH2Cl2 stirred at 24°C for 1 h;

[PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 → 4,5-Diazafluoren-9-one (50890-67-0) + palladium diacetate (3375-31-3)

Conditions	Yield
With oxygen; sodium acetate In 1,4-dioxane at 80℃; under 760.051 Torr;

palladium (II) nitrate + acetic acid (64-19-7) → palladium diacetate (3375-31-3)

Conditions	Yield
for 24h; Inert atmosphere; Reflux;	90%

trans-dinitratodiaquapalladium(II) (82279-70-7, 1147543-08-5) + acetic acid (64-19-7) → palladium diacetate (3375-31-3)

Conditions	Yield
In acetic acid Pd(II) nitrate dissolved in anhyd. acetic acid; stirred for 3 h at room temp.; suspn. diluted with acetic acid; centrifuged; washed (H2O, acetone); dried (vac., NaOH); elem. anal.;	85%

palladium (II) nitrate + acetic anhydride (108-24-7) → palladium diacetate (3375-31-3)

Conditions	Yield
In water soln. of Pd salt heated to 90°C, acetic anhydride added in a 2-4 molar excess to Pd; crystd., ppt. filtered, washed (hot glacial CH3COOH, 100-115°C), dried in air at room temp. or in drying box at temp. of up to 150°C; elem. anal., detd. by XRD, DTA;	80%

Pd(1,2-bis(diphenylphosphinoethane))(OCOMe)2 (73727-99-8) → [Pd(1,2-bis(diphenylphosphanyl)ethane)2](CH3COO)2 + palladium diacetate (3375-31-3) + palladium (7440-05-3)

Conditions	Yield
With 1,4-benzoquinone; CO; ethene In d(4)-methanol (N2); using Schlenk techniques; charging of NMR tube with a soln. of Pd(OAc)2(dppe) in CD3OD at room temp.; addn. of TsOH and 1,4-benzoquinone; holding for 1 h at room temp., treatment with CO/ethene (1:1) at 40 bar;heating at 85°C for 1 h; not isolated, detected by NMR;

(1,10-phenanthrolino)2-tetrapalladium(CO)(acetate)4 → (1,10-phenanthrolino)2-tetrapalladium(acetate)2 + (1,10-phenanthrolino)-tetrapalladium(acetate) + (1,10-phenanthrolino)2-tetrapalladium(acetate)3 + palladium diacetate (3375-31-3) + diacetato(1,10-phenantroline)palladium(II)

Conditions	Yield
With oxygen In acetic acid byproducts: CO2; heating of complex in AcOH in O2 atmosphere at 90°C;

palladium (II) acetate → palladium diacetate (3375-31-3)

Conditions	Yield
With nitric or HClO4 or methanesulfonic acid In acetic acid
With nitric or HClO4 or methanesulfonic acid In diethyl ether

palladium dichloride → palladium diacetate (3375-31-3)

Conditions

Yield

With potassium hydroxide; sodium tetrahydroborate; acetic acid In nitric acid; acetic acid addn. of KOH to an aq. soln. of PdCl2 to pH 8-9, reduction to Pd with NaBH4 (washing Cl(1-) free with H2O and CH3CO2H), addn. of glacial acetic acid and concd. HNO3, mixture was heated to boiling point during 1-1.5 h and boiled 4-5 h; filtn., evapn. of filtrate to 1/3 of orginal volume, crystn. on cooling, filtn., drying in a vacuum desiccator (over KOH); process yields Pd(OAc)2 free from Pd-nitrate;

70-75

palladium (7440-05-3) → palladium diacetate (3375-31-3)

Conditions	Yield
With nitric acid; acetic acid In acetic acid Pd-black oxidized with a conc. soln. of HNO3 and glacial acetic acid;

trans-dinitratodiaquapalladium(II) (82279-70-7, 1147543-08-5) + acetic acid (64-19-7) → palladium (II) acetate + palladium diacetate (3375-31-3)

Conditions	Yield
In water; acetic acid Pd(II) nitrate dissolved in mixt. of acetic acid and H2O; mixt. stirred for 3 h at room temp.; filtered; washed (glacial acetic acid, ether); dried (vac. over alkali);mixt. extd. (benzene); filtered; filtrate evapd. to dryness at 40.degre e.C in vac.; elem. anal.;	A 61% B n/a

palladium(II) oxide hydrate + acetic acid (64-19-7) → palladium diacetate (3375-31-3)

Conditions	Yield
In acetic acid stirring wet, freshly pptd. PdO in glacial AcOH (80°C, 2 h); solvent removal (vac., room temp.; over 10 h), drying (vac., over KOH, 85°C);

acetic acid (64-19-7) + palladium dichloride → palladium diacetate (3375-31-3)

Conditions	Yield
With sodium tetrahydroborate; nitric acid reacting PdCl2 and NaBH4, resulting Pd-black oxidation by conc. HNO3 andglacial acetic acid; refluxing with Pd-black in glacial acetic acid;

palladium (II) nitrate + acetic acid (64-19-7) + ethyl acetate (141-78-6) → palladium diacetate (3375-31-3)

Conditions	Yield
In water soln. of Pd salt heated to 80-90°C, ethyl acetate added, soln. heated to 90-100°C, glacial CH3COOH added gradually at temp. of 100-115°C, pptd.; crystd., ppt. filtered in hot state, washed (hot glacial CH3COOH, 100-115°C), dried in air at room temp. or in drying box at temp. of up to 150°C; elem. anal., detd. by XRD, DTA;

2,5-Dimethyl-1,4-benzoquinone (137-18-8) + [PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 → 4,5-Diazafluoren-9-one (50890-67-0) + 2,5-dimethylhydroquinone (615-90-7) + palladium diacetate (3375-31-3)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

2-tert-butyl-1,4-benzoquinone (3602-55-9) + [PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 → 4,5-Diazafluoren-9-one (50890-67-0) + palladium diacetate (3375-31-3) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

[PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 + 2-Methyl-1,4-benzoquinone (553-97-9) → 4,5-Diazafluoren-9-one (50890-67-0) + 2-methylbenzene-1,4-diol (95-71-6) + palladium diacetate (3375-31-3)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

[PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 + p-benzoquinone (106-51-4) → 4,5-Diazafluoren-9-one (50890-67-0) + palladium diacetate (3375-31-3) + hydroquinone (123-31-9)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

2-Chloro-1,4-benzoquinone (695-99-8) + [PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 → 4,5-Diazafluoren-9-one (50890-67-0) + palladium diacetate (3375-31-3) + chloro-p-hydroquinone (615-67-8)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

diazomethane (186581-53-3, 908094-01-9) + 6-bromo-3,4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane] (345964-51-4) + palladium diacetate (3375-31-3) → 6-bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane] (345964-52-5)

Conditions	Yield
In diethyl ether	100%
In diethyl ether	100%

N-allyloxycarbonylvaline methyl ester + tert-butyldimethylsilane (29681-57-0) + palladium diacetate (3375-31-3) → N-t-butyldimethylsilyloxycarbonylvaline methyl ester

Conditions	Yield
With ammonium chloride; triethylamine In dichloromethane	100%

palladium diacetate (3375-31-3) + 10,10-dimethyl-9,11-dioxo-1,5-dithia-8,12-diazacyclotetradecane (124398-54-5) → {Pd(C(CH3)2(CONHC2H4SCH2)2CH2)}

Conditions	Yield
With potassium carbonate In methanol; water Pd(OAc)2 react with the ligand in MeOH/H2O (1:1) containing K2CO3 (pH 9) at 15°C within 1 h; monitored by silica gel tlc (Kiesel gel 60 F254, MeOH) or hplc (weak cation resin, 0.1 m KH2PO4, detection: UV); elem. anal.;	100%

palladium diacetate (3375-31-3) + benzoic acid (65-85-0) → dibenzoatopalladium(II)

Conditions	Yield
In benzene-d6 heating at 90°C;	100%
In benzene Pd-compd. soln. stirring (1 h), filtration, org. acid addn., stirring; solvent evapn., washing (acetone), recrystn. (benzene), drying (vac.);	85%

(2-pyridylphenyl)mercury(II) chloride tetramer (106995-39-5) + palladium diacetate (3375-31-3) → 2-(2'-pyridyl)phenylpalladium(II) acetate * 0.5H2O

Conditions	Yield
With water In ethanol; dichloromethane a suspn. of Hg-compound in EtOH was added to a soln. of Pd(OAc)2 in CH2Cl2, mixt. was heated under reflux for 4 h; filtered through Celite, filtrate concd. in vacuo until a solid began to separate, ppt. was filtered off and dried; elem. anal.;	100%

N,N'-dimethylbenzylamine (103-83-3) + palladium diacetate (3375-31-3) + o-toluidine (95-53-4) → bisacetato-N,N-dimethylbenzylamine-o-toluidinepalladium(II) (93916-94-0)

Conditions	Yield
In dichloromethane o-toluidine in CH2Cl2 was added dropwise to Pd acetate in CH2Cl2, stirring for 5 min, Me2NCH2C6H5 in CH2Cl2 was added, stirring for 10 min; evapn., stirring with light petroleum, filtration; elem. anal.;	100%

palladium diacetate (3375-31-3) + 3,6-bis(4'-(butyloxy)phenyl)pyridazine → bis(μ-acetato)bis[3,6-bis(4'-(butyloxy)phenyl)pyridazine]dipalladium (438000-80-7, 373387-81-6)

Conditions	Yield
In acetic acid addn. of Pd acetate (2.63E-4 mol) to soln. of the pyridazine (2.63E-4 mol) in acetic acid, heating at 60°C for 6 h; solvent was removed;	100%

palladium diacetate (3375-31-3) + 3,6-bis(4'-(butyloxy)phenyl)pyridazine → dipalladium(μ-acetato)-3,6-bis(4'-butyloxyphenyl)pyridazine (373387-81-6, 438000-80-7)

Conditions	Yield
In acetic acid a soln. of pyridazine and Pd salt (1:1) in acetic acid heated at 60°C for 48 h; the solvent removed to yield a solid;	100%

palladium diacetate (3375-31-3) + 1,4-dimethyl-1,2,4-triazolium iodide (120317-69-3) → cis-diiodobis(1,4-dimethyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene)palladium(II)

Conditions	Yield
In tetrahydrofuran byproducts: HOAc; N2-atmosphere; refluxing Pd(OAc)2 with 2 equiv. of triazole derivative for 10 min; pptn. on cooling, solvent removal, washing (PhMe, H2O); elem. anal.;	100%

Upstream product

• 141-53-7 Sodium formate 
• 7803-57-8 Hydrazine hydrate 
• 7647-10-1 Palladium chloride 

Downstream Products

• 350683-40-8 ethyl indoline-6-carboxylate 
• 528521-89-3 (S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE 
• 528521-86-0 (R)-(+)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE 
• 20662-53-7 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE 
• 214360-73-3 4-Aminophenylboronic acid pinacol ester 
• 886851-50-9 2-MORPHOLINO-5-(TRIFLUOROMETHYL)BENZALDEHYDE 
• 528521-87-1 (R)-(+)-7,7'-BIS[DI(4-METHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE 
• 614-96-0 5-Methylindole 
• 54252-56-1 C-(3,4-DIHYDRO-2H-BENZO[1,4]OXAZIN-3-YL)-METHYLAMINE 
• 484-20-8 Bergapten 
• 31458-45-4 4,6-Diamino-2-pyrimidinol 
• 4993-96-8 1-ACETYL-5-AMINO-2,3-DIHYDRO-(1H)-INDOLE 
• 817176-80-0 (S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97% 
• 177976-49-7 3-PHENYLBENZYLAMINE 
• 501-65-5 Diphenylacetylene 
• 591-87-7 Allyl acetate 
• 90315-82-5 Ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 2458-26-6 3-Phenyl-1H-pyrazole 
• 15861-30-0 2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID 
• 2243-47-2 3-AMINOBIPHENYL 
• 19163-24-7 5-Phenylthiophene-2-carboxylic acid 
• 71205-17-9 (E)-METHYL 3-(4-BROMOPHENYL)ACRYLATE 
• 92-67-1 4-AMINOBIPHENYL 
• 15861-23-1 5-CYANO-2,3-DIHYDRO-1H-INDOLE 
• 19163-21-4 5-PHENYL-2-THIOPHENECARBALDEHYDE 
• 123847-85-8 N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine 
• 1008-91-9 1-(4-Pyridyl)piperazine 

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