[ CAS No. 14588-08-0 ] {[proInfo.proName]}

Name: 14588-08-0|Bis(triphenylphosphine)palladium(II) acetate|98%
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SKU: A258560
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2D 3D

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Quality Control of [ 14588-08-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14588-08-0 ]

SDS Specification

Alternatived Products of [ 14588-08-0 ]

Product Details of [ 14588-08-0 ]

CAS No. :	14588-08-0	MDL No. :	MFCD00010013
Formula :	C₄₀H₃₆O₄P₂Pd	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	749.08	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 14588-08-0 ]

Physicochemical Properties

Num. heavy atoms :	47
Num. arom. heavy atoms :	36
Fraction Csp3 :	0.05
Num. rotatable bonds :	12
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	194.21
TPSA :	79.78 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	9.42
Log Po/w (WLOGP) :	6.92
Log Po/w (MLOGP) :	6.64
Log Po/w (SILICOS-IT) :	6.77
Consensus Log Po/w :	5.95

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-10.19
Solubility :	0.000000048 mg/ml ; 0.0000000001 mol/l
Class :	Insoluble
Log S (Ali) :	-11.0
Solubility :	0.0000000075 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-15.22
Solubility :	0.0 mg/ml ; 6.01e-16 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	6.54

Safety of [ 14588-08-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14588-08-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 14588-08-0 ]

[ 14588-08-0 ] Synthesis Path-Downstream 1~12

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane-d2	54 A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of DANFABA (27 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product.

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane-d2	52 A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of tritylFABA (31 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red/black solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product.

3
[ 70096-12-7 ]
lithium(etherate)2.5 tetrakis(pentafluorophenyl)borate [ No CAS ]
[ 2206-26-0 ]
[Pd(OAc)(P(Ph)3)2(CD₃CN)][FABA] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 mumol) in CD3CN (0.5 mL) was stirred as a solution of Li(OEt2)2.5FABA (29 mg, 33.4 mumol) in CD3CN (0.5 mL) was added drop-wise via pipet. The resulting yellow solution was sealed in an NMR tube and subjected to NMR analysis. Result: Both 1H and 31P NMR analysis showed the formation of a single product. 31P{1H} NMR (CD3CN, delta): 32.8 (s).

Reference： [1]Patent: US2005/187398,2005,A1 .Location in patent: Page/Page column 24

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane-d2	53 A solution of Pd(OAc)2(PPh3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of Li(OEt2)2.5FABA (29 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product.

5
[ 14588-08-0 ]
[ 17966-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	In not given N2-atmosphere, 12 h;

Reference： [1]Goodfellow, John A.; Stephenson, T. Anthony; Cornock, Margaret T. [Journal of the Chemical Society, Dalton Transactions][Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1978, p. 1195 - 1200]

6
[ 70096-12-7 ]
[ 3375-31-3 ]
[ 603-35-0 ]
[Pd(triphenylphosphine)3(OAc)]OAc [ No CAS ]

Reference： [1]Kinetics and Catalysis,2007,vol. 48,p. 228 - 244

7
[ 3375-31-3 ]
[ 603-35-0 ]
[ 70096-12-7 ]

Reference： [1]Kinetics and Catalysis,2007,vol. 48,p. 228 - 244
[2]Kinetics and Catalysis,2007,vol. 48,p. 228 - 244

8
[ 3375-31-3 ]
[ 603-35-0 ]
[ 70096-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 100.0℃; for 0.166667 - 0.25h;Product distribution / selectivity;	A mixture of PPh3 (4.28 g, 16.3 mmol) and Pd(OAc)2 (1.83 g, 8.16 mmol) were stirred in DMF (90 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 10 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-methylimidazo[1,2-a]pyrazine (10.0 g, 40.8 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating at about 100° C. and a solution of 4-iodo-2-(methylthio)pyrimidine (20.56 g, 81.6 mmol) in DMF (40 mL) was added via addition funnel over about 4 h. The reaction was heated at about 100° C. for about 16 hours after the addition ended then cooled to ambient temperature and concentrated under reduced pressure. The resulting solid was dissolved in DCM (500 mL) and washed with 1 N HCl (5.x.200 mL) then washed with 0.5 N NaOH (200 mL) and filtered through Celite.(R). to break the resulting emulsion. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was filtered through a silica gel plug using EtOAc then concentrated under reduced pressure and dissolved in DCM (200 mL). The DCM solution was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, cut to 4:1 and held for 40 min, ramped to 1:1 over 20 min and held until product finished eluting). All product-containing fractions (including those with triphenylphosphine oxide) were combined and concentrated under reduced pressure until heavy precipitate present in a dark liquid. Then IPA was added and further concentrated under reduced pressure to remove DCM. The resulting suspension was filtered, washing with IPA followed by petroleum ether (b.p. 30-60° C.) and dried in vacuum oven at about 70° C. to give the title compound (5.7 g, 38percent): LC/MS (Table 1, Method a) Rt=3.39 min; MS m/z: 370.3 (M+H)+; A mixture of PPh3 (4.28 g, 16.3 mmol) and Pd(OAc)2 (1.83 g, 8.16 mmol) were stirred in DMF (90 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 10 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-methylimidazo[1,2-a]pyrazine (10.0 g, 40.8 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating at about 100° C. and a solution of 4-iodo-2-(methylthio)pyrimidine (20.56 g, 81.6 mmol) in DMF (40 mL) was added via addition funnel over about 4 h. The reaction was heated at about 100° C. for about 16 hours after the addition ended then cooled to ambient temperature and concentrated under reduced pressure. The resulting solid was dissolved in DCM (500 mL) and washed with 1 N HCl (5.x.200 mL) then washed with 0.5 N NaOH (200 mL) and filtered through Celite.(R). to break the resulting emulsion. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was filtered through a silica gel plug using EtOAc then concentrated under reduced pressure and dissolved in DCM (200 mL). The DCM solution was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, cut to 4:1 and held for 40 min, ramped to 1:1 over 20 min and held until product finished eluting). All product-containing fractions (including those with triphenylphosphine oxide) were combined and concentrated under reduced pressure until heavy precipitate present in a dark liquid. Then IPA was added and further concentrated under reduced pressure to remove DCM. The resulting suspension was filtered, washing with IPA followed by petroleum ether (b.p. 30-60° C.) and dried in vacuum oven at about 70° C. to give the title compound (5.7 g, 38percent): LC/MS (Table 1, Method a) Rt=3.39 min; MS m/z: 370.3 (M+H)+; A mixture of PPh3 (6.12 g, 23.3 mmol) and Pd(OAc)2 (2.62 g, 11.7 mmol) were stirred in DMF (136 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 15 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-ethylimidazo[1,2-a]pyrazine (15.1 g, 58.3 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating and a solution of 4-iodo-2-(methylthio)pyrimidine (29.4 g, 117 mmol) in DMF (60 mL) was added via syringe pump over about 8 hours. The reaction was heated for about 15 hours after the addition ended then concentrated under reduced pressure. The resulting crude material was dissolved in DCM (600 mL) and washed with 1 N HCl (5.x.300 mL) followed by 0.5 N NaOH (300 mL) then filtered the resulting emulsion through Celite.(R).. The layers of the filtrate were separated and the organic layer was washed with brine (2.x.300 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, ramped to 4:1 over 1 min, held for 35...

Reference： [1]Patent: US2008/249305,2008,A1 .Location in patent: Page/Page column 18; 20; 22-23

9
[ 70096-12-7 ]
[ 7664-93-9 ]
[ 15227-23-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; for 0.666667h;	To a 0.1mmol of trans-[Pd(OAc)2(PPh3)2] in 20mL EtOH a slight excess of H2SO4 was added dropwise. After ca. 10min a yellow solid precipitated. The suspension was stirred for 30 minutes more. After adding 20mL of petrol ether, the solid was collected on a filter, washed with H2O, EtOH, petroleum ether and dried under vacuum. Yield 80percent. Elem. anal. calcd for C36H30O4SP2Pd: C, 58.69, H, 4.08; found: C, 59.05; H, 4.06. NMR: 1H 7.66?6.94 (m, 30H, Ph), 31P{1H} 35.0 (s).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 767,p. 72 - 77

10
[ 14588-08-0 ]
[ 31989-57-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In tetrahydrofuran at 20℃; for 0.5h;	Synthesis of [(Ph₃P)₂Pd{C₆H₃-2-(N=N-N(Me)Ph)-5-COOEt}Br] (5): Bis(triphenylphosphane)palladium diacetate (315mg, 0.42mmol) was suspended in 10mL of anhydrous tetrahydrofuran. After the suspension was stirred for 10min, hydrazine monohydrate (11μL, 11.1mg, 0.22mmol) was added. The final clear greenish brown solution was stirred for 30minat r.t. Then 1-(2-bromo-4-ethoxycarbonylphenyl)-3-methyl-3-phenyltriazene (2) (152.5mg, 0.42mmol) was dissolved in anhydrous tetrahydrofuran (5mL) and added via a cannula to the thus prepared palladium(0) solution. The reaction mixture was heated to 60°C for 4h. After cooling to r.t. all volatiles were removed in vacuo. The residue was washed three times with n-pentane (3x5 mL). Then the crude product was washed twice with diethyl ether (2x3 mL). Drying in vacuo gave a grey-brown powder. Yield: 225mg of 5 (75%). Rerystallization was achieved in toluene/n-hexane yielding orange rhombohedral crystals. (0030) Physical data of 5: Dec. without melting. 1H NMR (600MHz, [D8]THF, 298K): δ=1.21 (t, J=7.1Hz, 3H, COOEt CH3), 3.73 (s, 3H, NCH3), 4.08 (q, J=7.1Hz, 2H, COOEt CH2), 6.43 (d, J=8.2Hz, 1H, subArH 6-CH), 7.01 (d, J=8.2Hz, 1H, subArH 3-CH), 7.04 (m, 1H, ArH 4-CH), 7.17 (t, J=7.5Hz, 12H, PPh3 2,2′-CH), 7.25 (t, J=7.3Hz, 6H, PPh3 4-CH), 7.30 (m, 5H, ArH 2,2′-CH, 3,3′-CH sub ArH 5-CH), 7.59 (m, 12H, PPh3 3,3′-CH). 13C{1H} NMR (150MHz, [D8]THF, 297K): δ=14.7 (COOEt CH3), 32.9 (NCH3), 60.0 (COOEt CH2), 117.2 (subAr 6-CH), 117.3 (Ar 2,2′-CH), 123.6 (Ar, 4-CH), 125.1 (subAr 3-CH), 128.0 (subAr CPd), 128.2 (t, 2JPC=5.1Hz, PPh3 2,2′-CH), 129.5 (PPh3 4-CH), 130.2 (Ar 3,3′-CH), 132.7 (t, 1JPC=22.9Hz, PPh3 1-C), 135.6 (t, 3JPC=6.3Hz, PPh3 3,3′-CH), 139.3 (t, 5JPC=4.6Hz, subAr 5-CH), 146.0 (Ar 1-CN), 156.9 (t 4JPC=2.5Hz, subAr 4-C), 158.4 (t, 3JPC=3.7Hz, subAr 1-CN), 166.1 (COOEt). 31P{1H} NMR (243MHz, [D8]THF, 297K): δ=23.56. HR-MS (ESI, acetonitrile), [(M-PPh3-Br)]+: calculated for C34H32N3O2PPd: 650.1196Da, found: 650.1219Da, Δm/z=5.5ppm. IR (ATR, cm-1): 3052, 1707, 1597, 1503, 1479, 1433, 1363, 1333, 1271, 1228, 1204, 1101, 1026, 994, 825, 742, 726, 687, 608, 520, 509, 492, 453, 438, 414. Elemental anal. (C52H46BrN3O2P2Pd): calcd.: C 62.88, H 4.67, Br 8.05, N 4.23; found: C 61.88, H 4.60, Br 7.43, N 3.75. TGA-DSC (m0=6.0109mg, 25°C-600°C, 5K/min): three step degradation, 1. step: 10.31% (216.9°C, proceeds exothermic with 25.9J/g), 2. step: 31.34% (309.3°C), 3. step: 31.8% (356.5°C), residue: 25.04%.

Reference： [1]Preusser, Silvio; Schönherr, Paul R.W.; Görls, Helmar; Imhof, Wolfgang; Krieck, Sven; Westerhausen, Matthias [Journal of Organometallic Chemistry, 2019, vol. 898]

11
[ 14588-08-0 ]
C₂₆H₂₀N₂O₂Se₂ [ No CAS ]
C₃₁H₂₄NOPPdSe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In dichloromethane for 3h; Reflux;

Reference： [1]Abram, Ulrich; Lang, Ernesto Schulz; Roca Jungfer, Maximilian [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 45, p. 4303 - 4312]

12
[ 14588-08-0 ]
[ 119307-23-2 ]
C₃₁H₂₄NOPPdTe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In dichloromethane for 3h; Reflux;

Reference： [1]Abram, Ulrich; Lang, Ernesto Schulz; Roca Jungfer, Maximilian [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 45, p. 4303 - 4312]

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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 14588-08-0 ] {[proInfo.proName]}

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[ 14588-08-0 ] Synthesis Path-Downstream 1~12

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