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Phosphine oxide, (1-phenyl-1,2-ethanediyl)bis[diphenyl-], also known as bis(diphenylphosphino)ethane (dppe), is a bidentate phosphine ligand widely used in homogeneous catalysis. It features a central ethanediyl (CH2CH2) backbone with two diphenylphosphino groups attached to each carbon atom. The phenyl rings in dppe provide steric bulk, which can influence the reactivity and selectivity of catalytic reactions. This ligand is particularly effective in transition metal-catalyzed processes, such as hydrogenation, hydroformylation, and cross-coupling reactions, due to its ability to form stable complexes with metals and its electronic properties that can modulate the catalyst's activity.

3583-85-5

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3583-85-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 3583-85-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,8 and 3 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 3583-85:
(6*3)+(5*5)+(4*8)+(3*3)+(2*8)+(1*5)=105
105 % 10 = 5
So 3583-85-5 is a valid CAS Registry Number.

3583-85-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (+/-)-1,2-bis(diphenylphosphino)phenylethane P,P'-dioxide

1.2 Other means of identification

Product number -
Other names 1-phenylethane-1 2-diyl bis 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:3583-85-5 SDS

3583-85-5Relevant academic research and scientific papers

An efficient base-catalyzed double addition of H-phosphine oxides to alkynes

Yoshimura, Aya,Saga, Yuta,Sato, Yuki,Ogawa, Akiya,Chen, Tieqiao,Han, Li-Biao

, p. 3382 - 3384 (2016)

An efficient base-catalyzed double addition of H-phosphine oxides to alkynes is developed. In the presence of a catalytic amount of a base, the addition of various H-phosphine oxides to both aromatic and aliphatic alkynes took place efficiently to produce the corresponding bisphosphoryl compounds in excellent yields. This method provides an easy direct way to prepare bisphosphine oxides that are of high importance in organic synthesis.

Alkali Metal Catalysed Double Hydrophosphorylation of Nitriles and Alkynes

Banerjee, Indrani,Harinath, Adimulam,Panda, Tarun K.

, p. 2224 - 2230 (2019)

Catalytic C–P and N–P bond formation via double hydrophosphorylation of nitriles with diphenylphosphane oxide using alkali metal precatalyst [MN(SiMe3)2] (M = Li, Na, K) is reported. The potassium congener was observed to be the most

Regioselective Single and Double Hydrophosphination and Hydrophosphinylation of Unactivated Alkynes

Basiouny, Miriam M. I.,Dollard, Deborah A.,Schmidt, Joseph A. R.

, p. 7143 - 7153 (2019/08/26)

A lanthanum-based N,N-dimethylbenzylamine complex was used as a precatalyst for both hydrophosphination and hydrophosphinylation of alkynes under mild conditions. In the case of hydrophosphination, the catalyst induced monoaddition with high regiospecific

BISPHOSPHINE OXIDE COMPOUND, BIS-THIO-PHOSPHINE COMPOUND, OR METHOD FOR PRODUCING BISPHOSPHINE COMPOUND

-

Paragraph 0022; 0023; 0024, (2018/06/12)

PROBLEM TO BE SOLVED: To provide a general synthesis method of various bisphosphine compounds and derivatives thereof by using raw materials that are easily available and easy to handle. SOLUTION: A bisphosphine oxide compound, a bis-thio-phosphine compou

T-BuOK-mediated reductive addition of P(O)-H compounds to terminal alkynes forming β-arylphosphine oxides

Zhang, Ji-Shu,Zhang, Jian-Qiu,Chen, Tieqiao,Han, Li-Biao

supporting information, p. 5462 - 5467 (2017/07/12)

A novel and efficient t-BuOK-mediated reductive addition of P(O)-H compounds to terminal alkynes was developed. A variety of β-arylphosphine oxides including the valuable β-heteroarylphosphine oxides were produced in moderate to high yields under mild reaction conditions. This reaction may proceed via a tandem process involving regio-selective double addition and subsequent transfer hydrogenation.

DOUBLE ADDITION OF PHOSPHINE OXIDE TO ALKYNE WITH BASE CATALYST

-

Paragraph 0067, (2017/09/06)

PROBLEM TO BE SOLVED: To provide a method of synthesizing a phosphorus compound by double addition of phosphine oxide to alkyne with a base catalyst. SOLUTION: The present invention provides a method comprising the step of reacting alkyne and a phosphorus compound in an ether solvent in the presence of a catalytic amount of a base. The method of production according to the present invention (1) allows a reduction in remaining metal components in the product and (2) a reduction in production cost and (3) has an expanded scope of substrates in comparison with the conventional methods of production. Moreover, the obtained compounds may be used in flame retardants, lubricant additives, pharmaceutical intermediates, and catalyst raw materials. Furthermore, phosphine compounds that are obtained by reducing the compounds obtained by this reaction are compounds useful as ligands. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Air-induced double addition of P(O)-H bonds to alkynes: A clean and practical method for the preparation of 1,2-bisphosphorylethanes

Guo, Haiqing,Yoshimura, Aya,Chen, Tieqiao,Saga, Yuta,Han, Li-Biao

supporting information, p. 1502 - 1506 (2017/05/10)

An air-induced double addition of diphenyl phosphine oxide to various alkynes is reported. This reaction can proceed efficiently under metal- and solvent-free conditions, and is a clean and practically useful method for the preparation of the valuable 1,2

Br?nsted Base Mediated Stereoselective Diphosphination of Terminal Alkynes with Diphosphanes

Okugawa, Yuto,Hirano, Koji,Miura, Masahiro

supporting information, p. 2973 - 2976 (2017/06/07)

A Br?nsted base mediated stereoselective diphosphination of terminal alkynes with diphosphanes proceeds to deliver the corresponding (E)-1,2-diphosphinoethenes in good yields. The reaction of aromatic alkynes occurs efficiently in the presence of a catalytic amount of LiO-t-Bu while MN(TMS)2 (M = Li or Na) gave better results in the case of aliphatic substrates. The Br?nsted base mediated protocol can offer a good alternative to precedented transition-metal-catalyzed or radical-promoted approaches to the 1,2-diphosphinoethene framework of potent interest in catalysis and coordination chemistry.

Reactions of Manganese and Rhenium Vinylidene Complexes with Hydrophosphoryl Compounds

Utegenov, Kamil I.,Krivykh, Vasilii V.,Mazhuga, Andrei M.,Chudin, Oleg S.,Smol'yakov, Aleksander F.,Dolgushin, Fedor M.,Goryunov, Evgenii I.,Ustynyuk, Nikolai A.

, p. 3903 - 3913 (2016/12/22)

We studied the reactions of manganese and rhenium phenylvinylidenes Cp(CO)2MCC(H)Ph (Mn1 M = Mn; Re1 M = Re) with HP(O)R2 (R = C6F5, Ph, and OEt) and HP(S)Ph2, which resulted in the selective formation of η2-E-phosphorylalkene complexes Cp(CO)2M{η2-E-H[R2(O)P]CC(H)Ph} (Mn2, Re2 R = C6F5; Mn3, Re3 R = Ph; and Mn6, Re6 R = OEt) and Cp(CO)2M{η2-E-H[Ph2(S)P]CC(H)Ph} (Mn5, Re5). The DFT/B3LYP(6-31G*) analysis showed the model reactions of Mn1 with HP(O)Me2 and HP(O) (OMe)2 to proceed via the initial transition state Cp(CO)2{Ph(H)CC}Mn···HO-PR2 (TS1) where the minor PA form HO-PR2 is hydrogen-bonded to the metal, followed by stereoselective (trans- to the phenyl group) addition of the PA phosphorus atom to the Cα-vinylidene atom, which defines both the rate of the process and the anti-Markovnikov structure of the reaction product. The reactions can proceed at a relatively low content of the reactive PA form.

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

Liu, Liu,Wang, Yulei,Zeng, Zhiping,Xu, Pengxiang,Gao, Yuxing,Yin, Yingwu,Zhao, Yufen

supporting information, p. 659 - 666 (2013/04/10)

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright

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