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Ethanone, 2-(diphenylphosphinyl)-1-phenyl-, also known as a phosphine oxide, is a chemical compound with the molecular formula C18H15O2P. It features a phenyl group and a carbonyl group attached to the phosphorus atom, giving it unique structural and functional properties. This versatile compound has been extensively studied for its potential applications in organometallic chemistry, catalysis, and medicine due to its ability to coordinate with metal ions and facilitate various chemical reactions, as well as its pharmacological properties such as antitumor and anti-inflammatory activities.

1733-58-0

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1733-58-0 Usage

Uses

Used in Organometallic Chemistry:
Ethanone, 2-(diphenylphosphinyl)-1-phenylis employed as a ligand in organometallic chemistry for its ability to coordinate with metal ions, which is crucial for the formation and stabilization of organometallic complexes. This coordination ability is essential for the development of new catalysts and the study of organometallic compounds' properties and reactivity.
Used in Catalysis:
As a ligand in catalysis, Ethanone, 2-(diphenylphosphinyl)-1-phenylplays a significant role in facilitating various chemical reactions. Its unique structure allows it to modulate the activity and selectivity of catalysts, making it a valuable component in the design of efficient and selective catalytic systems for a wide range of applications, including the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.
Used in Pharmaceutical Research:
Ethanone, 2-(diphenylphosphinyl)-1-phenylhas been investigated for its potential pharmacological properties, such as antitumor and anti-inflammatory activities. Its ability to coordinate with metal ions and interact with biological targets makes it a promising candidate for the development of new drugs and therapeutic agents, particularly in the areas of cancer treatment and inflammation management.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Ethanone, 2-(diphenylphosphinyl)-1-phenylis utilized for the design and synthesis of novel bioactive compounds. Its unique structural features and coordination chemistry enable the development of compounds with potential applications in various therapeutic areas, including the treatment of diseases such as cancer, inflammatory disorders, and other conditions that require targeted intervention at the molecular level.
Overall, Ethanone, 2-(diphenylphosphinyl)-1-phenylis a multifaceted compound with a broad range of applications in chemistry and medicine, making it an important subject of research and development for the advancement of scientific knowledge and the improvement of human health.

Check Digit Verification of cas no

The CAS Registry Mumber 1733-58-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,3 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1733-58:
(6*1)+(5*7)+(4*3)+(3*3)+(2*5)+(1*8)=80
80 % 10 = 0
So 1733-58-0 is a valid CAS Registry Number.

1733-58-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name phenacyldiphenylphosphine oxide

1.2 Other means of identification

Product number -
Other names (benzoylmethyl)diphenylphosphine oxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1733-58-0 SDS

1733-58-0Relevant academic research and scientific papers

X-ray crystallographic, luminescence and NMR studies of phenacyldiphenylphosphine oxide with the Ln(iii) ions Sm, Eu, Gd, Tb and Dy

Leach, Erin G.,Shady, Justin R.,Boyden, Adam C.,Emig, Anne-Lise,Henry, Alyssa T.,Connor, Emily K.,Staples, Richard J.,Schaertel, Stephanie,Werner, Eric J.,Biros, Shannon M.

, p. 15458 - 15469 (2017)

We report here the characterization in solution (NMR, luminescence, MS) and the solid-state (X-ray crystallography, IR) of complexes between phenacyldiphenylphosphine oxide and five Ln(iii) ions (Sm, Eu, Gd, Tb, Dy). Four single crystal X-ray structures are described here showing a 1:2 ratio between the Ln3+ ions Eu, Dy, Sm and Gd and the ligand, where the phosphine oxide ligands are bound in a monodentate manner to the metal center. A fifth structure is reported for the 1:2 Eu(NO3)3-ligand complex showing bidentate binding between the two ligands and the metal center. The solution coordination chemistry of these metal complexes was probed by 1H, 13C and 31P NMR, mass spectrometry, and luminescence experiments. The title ligand has the capability to sensitize Tb3+, Dy3+, Eu3+ and Sm3+ leading to metal-centered emission in solutions of acetonitrile and methanol and in the solid state.

Base-Promoted Direct Oxyphosphorylation of Alkynes with H-Phosphine Oxides in the Presence of Water

Zhong, Wenwu,Tan, Tao,Shi, Lei,Zeng, Xue

, p. 1379 - 1384 (2018)

We have developed a simple method for the oxyphosphorylation of arylalkynes to give β-keto phosphine oxides without the assistance of any transition metal. An inorganic base promoted the oxyphosphorylation and water played a synergistic role in the formation of various β-keto phosphine oxides. The reaction showed a wide structural scope and broad functional-group tolerance, and it proceeded under mild reaction conditions. This method solved the problem of metal dependence in the oxyphosphorylation of alkynes, providing a potential application in organic chemistry. Control experiments revealed the mechanism of the oxyphosphorylation and the synergistic role played by water in the radical process.

Silver-Catalyzed Aerobic Oxidative Decarboxylative Coupling of Arylpropiolic Acids with H-Phosphine Oxides: Mild and Facile Synthesis of β-Oxophosphine Oxides

Zeng, Yao-Fu,Tan, Dong-Hang,Lv, Wen-Xin,Li, Qingjiang,Wang, Honggen

, p. 4335 - 4338 (2015)

A silver-catalyzed oxidative decarboxylative coupling reaction of arylpropiolic acids with H-phosphine oxides by using air as the terminal oxidant was developed. The reaction proceeds smoothly under mild conditions to give β-oxophosphine oxides in moderate to good yields. Preliminary mechanistic studies were conducted. Aerobic oxidative decarboxylative coupling of arylpropiolic acids with H-phosphine oxides is realized under silver catalysis. The reaction proceeds smoothly under mild conditions to give β-oxophosphine oxides in moderate to good yields. Preliminary mechanistic studies are conducted.

A convenient approach to λ5-phosphinines via interaction of phosphorylated 3-pyrrolidinocrotonitrile with 2-bromoacetophenones

Svyaschenko, Yurii V.,Kostyuk, Alexandr N.,Barnych, Bogdan B.,Volochnyuk, Dmitriy M.

, p. 5656 - 5664 (2007)

The alkylation of 2-(diphenylphosphino)-3-pyrrolidin-1-ylbut-2-enenitrile with a set of bromoacetophenones has been studied. Cyclization of the phosphonium salts into 6-cyano-3-hydroxy-3-aryl-1,1-diphenyl-5-pyrrolidin-1-yl-1,2,3,4-tetrahydrophosphininium

Silver-Catalyzed Oxyphosphorylation of Unactivated Alkynes

Liu, Binbin,Song, Qingmin,Liu, Zhaohong,Wang, Zikun

supporting information, p. 3214 - 3219 (2021/05/27)

Here, we describe an application of hydroazidation in the instant activation of alkynes for achieving the oxyphosphorylation of unactivated alkynes with diarylphosphinoyl radicals under mild reaction conditions. This reaction provides a method for accessing β-ketophosphine oxides and phosphorus-containing pyrroles. (Figure presented.).

Synthesis of tertiary phosphine oxides by alkaline hydrolysis of quaternary phosphonium zwitterions using excess t-BuOK and stoichiometric water

Zhong, Chun-Hong,Huang, Wenhua

supporting information, p. 1537 - 1546 (2021/01/07)

Hydrolysis of quaternary arylphosphonium zwitterions bearing COO? and those in situ generated from the corresponding salts bearing Ac or OH at the aryl ring by using excess t-BuOK and stoichiometric water affords tertiary arylphosphine oxides in moderate to excellent yield, in contrast to hydrolysis of these zwittertion or salts in aqueous NaOH that mainly provides phosphine oxides with the loss of the aryl group. Under the t-BuOK/water conditions, hydrolysis of carbonyl stabilized ylides Ph3P = CHCOR (R = Ph, Me, and OEt), which partially exist as phosphonium enolates, prefers to produce Ph2P(O)CH2COR. Further reduction of Ph2P(O)CH2COMe by PhSiH3 allows the preparation of Ph2PCH2COMe in 43% yield.

Visible light-mediated photocatalytic phosphorylation of vinyl azides: A mild synthesis of β-ketophosphine oxides

Jung, Hye Im,Kim, Dae Young

, p. 380 - 387 (2019/12/24)

The photoredox-catalyzed phosphorylation of vinyl azides is described in this paper. The reaction proceeded smoothly using an inexpensive and easily-accessible Eosin Y as a photocatalyst under mild reaction conditions without any other oxidant, metal, or

Iron-Catalyzed and Air-Mediated C(sp3)?H Phosphorylation of 1,3-Dicarbonyl Compounds Involving C?C Bond Cleavage

Ou, Yingcong,Huang, Yuanting,Liu, Yu,Huo, Yanping,Gao, Yang,Li, Xianwei,Chen, Qian

supporting information, p. 5783 - 5787 (2020/11/30)

A C(sp3)?H phosphorylation has been achieved via the iron-catalyzed cross-coupling reactions between 1,3-dicarbonyl compounds and P(O)?H compounds involving C?C bond cleavages with air as the oxidant. This transformation provides a straightforward way to construct C(sp3)?P bonds, leading to the formation of β-ketophosphine oxides in up to 93% yield with good functional group tolerance. (Figure presented.).

An efficient preparation of β-ketophosphine oxides from alkynylphosphine oxides with benzaldehyde oxime as a hydroxide source

Chen, Lu-Lu,Zhang, Jing-Wen,Yang, Wan-Wan,Chen, Pei,Chen, Dan-Yun,Wang, Yan-Bo

, p. 3003 - 3009 (2019/03/20)

An effective and facile transitio-metal-free method has been developed for the synthesis of β-ketophosphine oxides from alkynylphosphine oxides with benzaldehyde oxime as a hydroxide surrogate. The current methodology provides simple access to various β-ketophosphine oxides in moderate to excellent yields with a broad substrate scope.

Cobalt(II)-Catalyzed Bisfunctionalization of Alkenes with Diarylphosphine Oxide and Peroxide

Shen, Jian,Xiao, Bo,Hou, Yang,Wang, Xue,Li, Gui-Zhi,Chen, Jin-Chun,Wang, Wei-Li,Cheng, Jian-Bo,Yang, Bin,Yang, Shang-Dong

supporting information, p. 5198 - 5209 (2019/11/13)

The low-cost cobalt(II) catalyst has been used for the first time to achieve P(O)-radical-mediated bisfunctionalization of alkenes with diarylphosphine oxide and peroxides. This simple process is performed under mild conditions to afford a wide variety of phosphonation-peroxidation products in a one-pot manner. Computational studies are carried out to provide a theoretical support for the P(O)-radical-involved bisfunctionalization of alkenes. (Figure presented.).

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