932710-63-9

Basic information

• Product Name: Bis(di-tert-butyl)-4-dimethylaminophenylphosphine
• Synonyms: Bis(di-tert-butyl)-4-dimethylaminophenylphosphine;[(4-Dimethylaminophenyl)]di(tert-butyl)phosphine;[4-(Dimethylamino)phenyl]bis(tert-butyl)phosphine;N,N-Dimethyl 4-(di(tert-butyl)phosphino)aniline;95% A-taPhos;(4-(N,N-DiMethylaMino)phenyl)di-tert-butyl phosphine,95% A-taPhos;(4-(N,N-DiMethylaMino)phenyl)di-tert-butyl phosphine,95%;[4-(N,N-DiMethylaMino)phenyl]di-t-butylphosphine, Min. 95% aMphos
• CAS NO: 932710-63-9
• Molecular Formula: C₁₆H₂₈NP
• Molecular Weight: 265.378
• Product Categories: Achiral Phosphine;Aryl Phosphine
• Mol File: 932710-63-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 57-61°C
• Boiling Point: 349.1±25.0 °C(Predicted)
• Appearance: white to light-brown/crystal
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Acetone
• PKA: 4.73±0.24(Predicted)
• CAS DataBase Reference: Bis(di-tert-butyl)-4-dimethylaminophenylphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(di-tert-butyl)-4-dimethylaminophenylphosphine(932710-63-9)
• EPA Substance Registry System: Bis(di-tert-butyl)-4-dimethylaminophenylphosphine(932710-63-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 932710-63-9(Hazardous Substances Data)

Usage

Description

Bis(di-tert-butyl)-4-dimethylaminophenylphosphine is an organophosphine compound characterized by its two di-tert-butyl groups and a 4-dimethylaminophenyl group attached to a central phosphorus atom. This unique structure endows it with versatile chemical properties and potential applications in various fields.

Uses

Used in Electrophotographic Applications:
Bis(di-tert-butyl)-4-dimethylaminophenylphosphine is used as a component in electrophotographic photoreceptors, process cartridges, and image forming electrodes. Its incorporation enhances the performance and durability of these devices, leading to improved image quality and reliability.
Used in Catalyst Preparation:
As a ligand, Bis(di-tert-butyl)-4-dimethylaminophenylphosphine is used to prepare a palladium dichloride catalyst (678740) upon treatment with PdCl2(COD). This catalyst is effective in cross-coupling aryl boronic acids with heteroaryl chlorides, facilitating the synthesis of various organic compounds and pharmaceuticals.
Used as an Organophosphine Ligand:
Due to its organophosphine nature, Bis(di-tert-butyl)-4-dimethylaminophenylphosphine can be employed as a ligand in various chemical reactions. Its unique steric and electronic properties make it a valuable component in the development of new catalysts and coordination complexes for a wide range of applications in organic synthesis, materials science, and pharmaceutical chemistry.

Reaction

Ligand used in a highly-active palladium precatalyst for the efficient amination of aryl chloride. Ligand used in the palladium-catalyzed annulations under microwave enhanced conditions.

InChI:InChI=1S/C16H28NP/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8/h9-12H,1-8H3

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 13716-10-4 di(tert-butyl)chlorophosphine 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 108949-55-9 4-N,N-dimethylaminophenyl magnesium chloride 
• 819-19-2 di-tert-butylphosphine 

Downstream Products

• 1356681-60-1 9-{5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-o-[4-(1,3-oxazol-2-yl)benzyl]-β-D-ribofuranosyl}-6-[2-(trimethylsilyl)ethoxy]-9H-purine 
• 1233717-68-4 bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium⁽⁰⁾ 
• 887919-35-9 bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) 
• 1820817-64-8 [4-(di-tert-butylphosphino)-N,N-dimethylaniline-2-(2’-aminobiphenyl)]palladium(II) methanesulfonate 

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.

Di-tert-butyl - 4 - dimethyl amino phosphonate and double (di-tert-butyl - 4 - dimethyl amino phosphonate) preparation method of catalysts

The invention provides a preparing method for di-tertiary butyl-4-dimethylamino phenylphosphine. Di-tertiary butylphosphine is subjected to low-temperature lithiation under shielding of inert gas and then reacts with N,N-dimethyl p-chloroaniline, and di-tertiary butyl-4-dimethylamino phenylphosphine is obtained. According to the preparing method, di-tertiary butyl-4-dimethylamino phenylphosphine is purified after a quenching reaction. The invention further provides a preparing method for bis(di-tertiary butyl-4-dimethylamino phenylphosphine) palladium chloride. Di-tertiary butyl-4-dimethylamino phenylphosphine obtained through the preparing method is further subjected to complexation with (1,5-cyclooctadiene) palladium dichloride or bispalladium dichloride. A di-tertiary butyl-4-dimethylamino phenylphosphine ligand is prepared through the novel method, purified and then subjected to palladium complexation, and the preparing yield is greatly increased; meanwhile, the loss of palladium is reduced, the preparing cost is greatly reduced, and the obtained products are high in purity and good in quality.