29949-69-7

Usage

Uses

Used in Organometallic and Coordination Chemistry:
Chloro(tert-butyl)phenylphosphine is used as a ligand for stabilizing metal complexes in organometallic and coordination chemistry. Its unique structure allows it to form stable bonds with metal ions, enhancing the stability and reactivity of the resulting complexes.
Used in Synthesis of Organic Compounds:
Chloro(tert-butyl)phenylphosphine is used as a reagent in the synthesis of various organic compounds. Its ability to form stable bonds with metal ions makes it a valuable component in the preparation of complex organic molecules.
Used in Catalysis:
Chloro(tert-butyl)phenylphosphine has been studied for its potential applications in catalysis. Its unique structure and bonding capabilities make it a promising candidate for use in catalytic processes, where it can facilitate chemical reactions and improve their efficiency.
Used as a Precursor for Phosphine Complexes:
Chloro(tert-butyl)phenylphosphine is used as a precursor for the preparation of phosphine complexes with transition metals. These complexes have a wide range of applications in various fields, including catalysis, materials science, and pharmaceuticals.

InChI:InChI=1/C10H14ClP/c1-10(2,3)12(11)9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 25979-07-1 tert-butyldichlorophosphine 
• 677-22-5 tert-butylmagnesium chloride 
• 644-97-3 Dichlorophenylphosphine 
• 62839-84-3 tert.-butyl-phenylthiophosphinic chloride 
• 507-20-0 tertiary butyl chloride 
• 594-19-4 tert.-butyl lithium 
• 1079-66-9 chloro-diphenylphosphine 
• 100-59-4 phenylmagnesium chloride 
• 98976-30-8 tert-Butylphenylphosphine oxide 
• 2259-30-5 tert-butylmagnesium bromide 
• 4923-85-7 tert-butylphenylphosphinic acid chloride 

Downstream Products

• 72170-79-7 1,2-di-t-butyl-1,2-diphenyldiphosphane monoxide 
• 98976-30-8 tert-Butylphenylphosphine oxide 
• 55793-26-5 1,2-di(tert-butyl)-1,2-diphenyl-diphosphine 
• 136847-44-4 N--N,N'-dimethyl-N'-(trimethylsilyl)harnstoff 
• 136847-45-5 1,5-di-t-butyl-2,4-dimethyl-1,5-diphenyl-2,4-diaza-1,5-diphosphapentan-3-one 
• 107487-23-0 α-naphtylphenylmethylsilyl t-butylphenyl-phosphinite 
• 107487-26-3 α-naphtylphenylmethylsilyl t-butylphenyl-phosphinate 
• 122345-31-7 Di-tert-butylphosphino(phenyl-tert-butylphosphino)schwefeldiimid 
• 4923-85-7 tert-butylphenylphosphinic acid chloride 
• 75-77-4 chloro-trimethyl-silane 
• 84674-91-9 1-(tert-Butyl-phenyl-phosphanyl)-1H-imidazole 
• 181825-83-2 tert-Butyl-phenyl-(2-trimethylsilanyloxy-naphthalen-1-yl)-phosphane 
• 185509-28-8 2-tert-butylphenylphosphanyl-4-methylphenol 
• 182195-99-9 C₁₆H₁₈ClOP 

Relevant academic research and scientific papers

Facial conversion of secondary phosphine oxides R1R2P(O)H to chlorophosphines R1R2PCl by acetyl chloride

A practically useful protocol for the reductive transformation of secondary phosphine oxides R1R2P(O)H to chlorophosphines R1R2PCl using acetyl chloride was disclosed. Various secondary phosphine oxides could be readily reduced to the corresponding chlorophosphines in high yields under mild conditions.

Symmetrical and unsymmetrical diphosphanes with diversified alkyl, aryl, and amino substituents

We present the comprehensive study of diphosphanes with diversified substituents regarding their syntheses, structures, and properties. To this end, we have synthesized a series of novel unsymmetrical alkyl, aryl and amino-substituted diphosphanes of the general formula R1R2P-PR3R4 (where R1, R2, R3, R4 = tBu, Ph, Et2N or iPr2N) via a salt metathesis reaction of halophosphanes with metal phosphides in high yield. We vastly expanded this group of compounds by obtaining the first mono- A nd tri-amino-substituted systems. The structures of the isolated compounds were characterized by NMR spectroscopy and X-ray diffraction. The isolated unsymmetrical diphosphanes have no tendency to rearrange to the corresponding symmetrical species. Additionally, we proposed the general classification of diphosphanes based on the number of different groups attached to phosphorus atoms and their distribution within a molecule. To investigate the impact of substituents on the properties of P-centers and a molecule as a whole, we conducted a DFT study on the electronic and steric properties of the obtained systems. The experimental and theoretical results can be very useful for designing P-P systems with desired properties.

Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols

Two catalyst systems are described, which together provide mild and general conditions for the Pd-catalyzed C-O cross-coupling of primary alcohols. For activated substrates, such as electron-deficient aryl halides, the commercially available ligand L2 promotes efficient coupling for a variety of alcohol nucleophiles. In the case of unactivated electrophiles, such as electron-rich aryl halides, the new ligand L8 was developed to improve these challenging C-O bond-forming reactions.

The reactivity of arylphosphorus acid amides under Birch reduction conditions

Several classes of arylphosphorus acid amides have been tested in reactions with alkali metal solutions in liquid ammonia. The outcomes of such reactions depend on the structures of the starting materials. Generally, two processes-Birch reduction or cleavage of the P-aryl bond-can be operative. Diarylphosphinic amides tend to undergo double Birch reduction to afford bis(cyclohexadienyl)phosphinic amides. Copyright

Simple unprecedented conversion of phosphine oxides and sulfides to phosphine boranes using sodium borohydride

A variety of phosphine oxides and sulfides can be efficiently converted directly to the corresponding phosphine boranes using oxalyl chloride followed by sodium borohydride. Optically active P-stereogenic phosphine oxides can be converted stereospecifically to phosphine boranes with inversion of configuration by treatment with Meerwein's salt followed by sodium borohydride.

Reactivity of allyl anions of allylphosphine-boranes towards electrophiles

The reactivity of mesomeric carbanions derived from allylphosphine-boranes varies as a function of electrophile. Small sp3-electrophiles react predominantly at the α carbon atom whereas bulky sp3- electrophiles and carbonyl compounds react mainly at the γ carbon. In the case of electron-deficient aldehydes reduction of carbonyl group and formation of the corresponding alcohols is observed. This is attributed to the weakly reducing properties of carbanions derived from allylphosphine-boranes, whose mesomeric form resembles the structure of a modified borohydride. ARKAT-USA, Inc.

Highly efficient reusable polymer-supported Pd catalysts of general use for the Suzuki reaction

Short and efficient syntheses of various polymer-supported Pd catalysts are reported. The reactivity of these catalysts has been determined for the Suzuki reaction. It turned out that the (tert-butylphenylphosphinomethyl)polystyrene-supported Pd catalyst 2′a is highly efficient for versatile Suzuki reactions from aryl chlorides. These couplings are performed in the presence of low amounts (4 mequiv) of supported Pd, the catalyst can be reused more than seven times without loss of efficiency and the Pd leaching is extremely low (0.1% of the initial amount).

Conjugate phosphination of cyclic and acyclic acceptors using Rh(I)-phosphine or Rh(I)-carbene complexes. Probing the mechanism with chirality at the silicon atom or the phosphorus atom of the Si-P reagent

The Rh(I)-catalyzed conjugate phosphinyl transfer from an Si-P reagent to an electron-deficient acceptor requires individual protocols for cyclic and acyclic α,β-unsaturated carbonyls and carboxyls. While 1,4-addition to cyclic acceptors is catalyzed by a

Synthesis of building blocks for the development of the SUPRAPhos ligand library and examples of their application in catalysis

We have previously introduced the SUPRAPhos ligand library, which is based on components that are self-assembled through nitrogen-zinc interactions, and report here an extension of this library, which widens the scope for application in asymmetric homogeneous catalysis. For example, we report the synthesis of phosphorus amidite appended porphyrins and building blocks with stereogenic centers at the phosphorus. With the new building blocks described in this paper we can form a 450-membered SUPRAPhos library, which is based on 45 building blocks (30 pyridyl phosphorus ligands and 15 complementary porphyrin-appended phosphorus ligands). Examples of the use of members of the library in the rhodium-catalyzed asymmetric hydroformylation of styrene are included. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Highly efficient and reusable supported Pd catalysts for Suzuki-Miyaura reactions of aryl chlorides

Syntheses of air- and moisture-stable heterogeneous (tert- butylarylphosphino)polystyrene-supported Pd catalysts and their use for versatile Suzuki-Miyaura reactions of aryl chlorides and arylboronic acids under non-anhydrous conditions are reported. The catalysts are easily recovered by filtration. They can be used many times (more than seven) without showing any loss of activity, and the amount of Pd leached is extremely low (0.1%).