887919-35-9

Basic information

• Product Name: BIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM(II)
• Synonyms: Pd(aMphos)Cl2, 15% Pd, Product of UMicore;Bis[4-[bis(1,1-diMethylethyl)phosphino-κ…;Palladium,bis[4-[bis(1,1-dimethylethyl)phosphino-kP]-N,N-dimethylbenzenamine]dichloro-, (SP-4-1)-;palladium(2+) ion bis(4-(di-tert-butylphosphanyl)-N,N-dimethylaniline) dichloride;Dichlorobis[di-tert-butyl(4-diMethylaMinophenyl)phosphine]palladiuM(II);Bis(4-(di-tert-Butylphosphanyl)-N,N-dimethylaniline);Dichlorobis{[4-(N,N-dimethylamino)phenyl]di-t-butylphosphino}palladium(II), min. 98%;BIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM(II)
• CAS NO: 887919-35-9
• Molecular Formula: C₃₂H₅₆Cl₂N₂P₂Pd
• Molecular Weight: 708.082
• EINECS: 1308068-626-2
• Product Categories: Pd
• Mol File: 887919-35-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 349.1ºC at 760 mmHg
• Flash Point: 164.9ºC
• Appearance: yellow/Powder
• Vapor Pressure: 4.82E-05mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: BIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM(II)(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM(II)(887919-35-9)
• EPA Substance Registry System: BIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM(II)(887919-35-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 887919-35-9(Hazardous Substances Data)

Usage

Reaction

Useful catalyst for the Suzuki Cross-Coupling of dioxolanylethyltrifluorborate and aryl/heteroaryl chlorides. Useful catalyst for the Suzuki Cross-Coupling of benzyloxyethyltrifluoroborate.

Chemical Properties

Yellow powder

Uses

Different sources of media describe the Uses of 887919-35-9 differently. You can refer to the following data:
1. Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium is useful catalyst for the Suzuki Cross-Coupling of dioxolanylethyltrifluorborate and aryl/heteroaryl chlorides.
2. Dichlorobis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) is a highly active, air-stable catalyst for Suzuki-Miyaura cross-coupling with aryl halides including 5- and 6-membered heteroaryl chlorides.

InChI:InChI=1/2C16H28NP.2ClH.Pd/c2*1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;;;/h2*9-12H,1-8H3;2*1H;/q;;;;+2/p-2

Synthetic route

dichloro(1,5-cyclooctadiene)palladium(II) (12107-56-1) + (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine (932710-63-9) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h; Solvent; Inert atmosphere;	97%

dichloro bis(acetonitrile) palladium(II) (21264-30-2, 90243-59-7, 14592-56-4) + (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine (932710-63-9) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 9.5h; Inert atmosphere;	1445 g

4-N,N-dimethylaminophenyl magnesium chloride (108949-55-9) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: copper chloride / 0.17 h / -30 °C / Inert atmosphere 1.2: 0.5 h / -30 °C 2.1: tetrahydrofuran / 9.5 h / 20 °C / Inert atmosphere View Scheme

4-dimethylaminophenylmagnesium bromide (7353-91-5) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: copper bromide / 0.13 h / -60 °C / Inert atmosphere 1.2: 0.5 h / -60 °C 2.1: tetrahydrofuran / 9.5 h / 20 °C / Inert atmosphere View Scheme

4-chloro-N,N-dimethylaniline (698-69-1) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 50 - 60 °C / Inert atmosphere 2.1: copper chloride / 0.17 h / -30 °C / Inert atmosphere 2.2: 0.5 h / -30 °C 3.1: tetrahydrofuran / 9.5 h / 20 °C / Inert atmosphere View Scheme

4-bromo-N,N-dimethylaniline (586-77-6) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 45 - 50 °C / Inert atmosphere 2.1: copper bromide / 0.13 h / -60 °C / Inert atmosphere 2.2: 0.5 h / -60 °C 3.1: tetrahydrofuran / 9.5 h / 20 °C / Inert atmosphere View Scheme

4-Iodo-N,N-dimethylaniline (698-70-4) → bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 2.1: copper iodide / 0.2 h / 0 °C / Inert atmosphere 2.2: 0.5 h / -60 °C 3.1: tetrahydrofuran / 9.5 h / 20 °C / Inert atmosphere View Scheme

(2-ethoxypyridin-3-yl)boronic acid (854373-97-0) + bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9) + tert-butyl (3R)-4-[4-bromo-3-fluoro-2-(methoxycarbonyl)phenyl]-3-ethylpiperazine-1-carboxylate → tert-butyl (3R)-4-[4-(2-ethoxypyridin-3-yl)-3-fluoro-2-(methoxycarbonyl)phenyl]-3-ethylpiperazine-1-carboxylate

Conditions	Yield
With potassium carbonate	87%

bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (887919-35-9) + (2-ethoxyphenyl)boronic acid (213211-69-9) + tert-butyl N-{3-[(5-bromo-2-{4-[2-cyano-4-(trifluoromethyl)phenyl]piperazin-1-yl}phenyl)formamido]propyl}carbamate → tert-butyl N-{3-[(4-{4-[2-cyano-4-(trifluoromethyl)phenyl]piperazin-1-yl}-2'-ethoxy-[1,1'-biphenyl]-3-yl)formamido]propyl}carbamate

Conditions	Yield
With potassium carbonate	87%

Upstream product

• 12107-56-1 dichloro(1,5-cyclooctadiene)palladium(II) 
• 932710-63-9 (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine 
• 21264-30-2 dichloro bis(acetonitrile) palladium(II) 
• 108949-55-9 4-N,N-dimethylaminophenyl magnesium chloride 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 698-70-4 4-Iodo-N,N-dimethylaniline 

Relevant articles and documents

Preparation method for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium

The invention discloses a preparation method for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium. The preparation method comprises the following steps that 1, a Grignard reagent isprepared from the raw materials of N, N-dimethyl p-haloaniline and magnesium chips; 2, the Grignard reagent is taken and cooled, then a catalyst is added for reaction, then di-tert-butylchlorophosphane is dropwise added, and heating is carried out for reaction so as to obtain di-tert-butyl-4-dimethylaminophenylphosphine; 3, the di-tert-butyl-4-dimethylaminophenylphosphine is purified; and 4, complexing bis(acetonitrile)dichloropalladium and the purified di-tert-butyl-4-dimethylaminophenylphosphine so as to obtain a target product. The preparation method has the advantages that the di-tert-butyl-4-dimethylaminophenylphosphine is purified, the high-purity di-tert-butyl-4-dimethylaminophenylphosphine is used for reacting with the bis(acetonitrile)dichloropalladium, and therefore the yield loss of the noble metal palladium is greatly reduced, the preparation cost is greatly lowered, and the method has a good practical value.