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1,2-Bis(phenylphosphino)ethane, also known as DPPE, is a chemical compound with the molecular formula C26H24P2. It is a phosphine ligand that is widely used in coordination chemistry and organometallic chemistry for the synthesis of transition metal complexes. DPPE features two phosphine arms with phenyl groups attached to the phosphorus atoms, which provide steric and electronic properties that are advantageous for binding to transition metal centers. 1,2-BIS(PHENYLPHOSPHINO)ETHANE is known for its role in the creation of metal complexes with specific applications in various fields.

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  • 18899-64-4 Structure
  • Basic information

    1. Product Name: 1,2-BIS(PHENYLPHOSPHINO)ETHANE
    2. Synonyms: ETHYLENE-BIS-PHENYLPHOSPHINE;1,2-BIS(PHENYLPHOSPHINO)ETHANE;1,2-BIS(PHENYLPHOSPHINO)ETHANE, TECH.;1,2-Ethanediylbis(phenylphosphine);Einecs 242-649-4;1,2-Bis(phenylphosphino)ethane, Min. 95% (10wt% in hexane);1,2-Bis(phenylphoshino)ethane, Min. 90%;1,2-Bis(phenylphosphino)ethane (10wt% in hexanes)
    3. CAS NO:18899-64-4
    4. Molecular Formula: C14H16P2
    5. Molecular Weight: 246.22
    6. EINECS: 242-649-4
    7. Product Categories: Achiral Phosphine;Aryl Phosphine;P-H
    8. Mol File: 18899-64-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 378.1°Cat760mmHg
    3. Flash Point: 182.5°C
    4. Appearance: /
    5. Density: g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Sensitive: air sensitive
    11. CAS DataBase Reference: 1,2-BIS(PHENYLPHOSPHINO)ETHANE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1,2-BIS(PHENYLPHOSPHINO)ETHANE(18899-64-4)
    13. EPA Substance Registry System: 1,2-BIS(PHENYLPHOSPHINO)ETHANE(18899-64-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. RIDADR: 2845
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 4.2
    8. PackingGroup: I
    9. Hazardous Substances Data: 18899-64-4(Hazardous Substances Data)

18899-64-4 Usage

Uses

Used in Catalysis Industry:
1,2-BIS(PHENYLPHOSPHINO)ETHANE is used as a phosphine ligand for the synthesis of transition metal complexes, which are essential in catalytic applications for the production of organic compounds. The steric and electronic properties of DPPE enhance the efficiency and selectivity of these catalytic processes.
Used in Material Science:
1,2-BIS(PHENYLPHOSPHINO)ETHANE is utilized as a component in the development of new materials with tailored properties. The ability of DPPE to form stable complexes with transition metals allows for the creation of materials with specific characteristics, such as improved catalytic activity or unique electronic properties.
Used in Molecular Imaging:
1,2-BIS(PHENYLPHOSPHINO)ETHANE is employed in the preparation of metal complexes for use in molecular imaging. The complexes formed with DPPE can be designed to have specific binding affinities or optical properties, making them suitable for imaging applications in fields such as medicine and biochemistry.
Used in Organic Reactions:
DPPE is used as a catalyst in various organic reactions. The metal complexes formed with 1,2-BIS(PHENYLPHOSPHINO)ETHANE can facilitate a range of organic transformations, improving the yield and selectivity of these reactions. This application is particularly relevant in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 18899-64-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,8,9 and 9 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 18899-64:
(7*1)+(6*8)+(5*8)+(4*9)+(3*9)+(2*6)+(1*4)=174
174 % 10 = 4
So 18899-64-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H16P2/c1-3-7-13(8-4-1)15-11-12-16-14-9-5-2-6-10-14/h1-10,15-16H,11-12H2

18899-64-4SDS

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 phenyl(2-phenylphosphanylethyl)phosphane

1.2 Other means of identification

Product number -
Other names EINECS 242-649-4

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:18899-64-4 SDS

18899-64-4Relevant articles and documents

Mechanism of phosphorus-carbon bond cleavage by lithium in tertiary phosphines. An optimized synthesis of 1,2-bis(phenylphosphino)ethane

Dogan, John,Schulte, Jurgen B.,Swiegers, Gerhard F.,Wild, S. Bruce

, p. 951 - 957 (2000)

Conditions influencing the extent of P-C(aryl) vs P-C(alkyl) bond cleavage in the reaction of Ph2P(CH2)2PPh2 with lithium in THF have been investigated. The results complement and elucidate earlier work; they indicate that the mechanism of P-C bond cleavage in tertiary phosphines of this type involves a thermodynamic equilibrium between P-C(aryl) and P- C(alkyl) cleaved radicals and anions, followed by reaction and stabilization of these as lithium salts. The addition of water to the reaction mixture causes a reestablishment of the cleavage equilibrium prior to the formation of the secondary phosphines. A mechanism involving competitive release of leaving groups as the thermodynamically most stable anion or radical has been proposed. The preparation of (R*, R*)-(±)/(R*, S*)-PhP(H)(CH2)2P(H)Ph by this route has been optimized.

The synthesis and characterisation of bis(phenylpyridylphosphino)ethane

Butler, Ian R.,Licence, Peter,Coles, Simon J.,Hursthouse, Michael B.

, p. 103 - 107 (2000)

A novel synthesis has been devised for the preparation of unsymmetrical phosphine substituted derivatives of bis(diphenylphosphino)ethane [dppe]. The title ligand has been prepared in a two step procedure from dppe. A palladium(II) complex of this new ligand has been prepared and characterised by single crystal X-ray diffraction.

Zirconium-Catalyzed Intermolecular Double Hydrophosphination of Alkynes with a Primary Phosphine

Bange, Christine A.,Waterman, Rory

, p. 6413 - 6416 (2016)

Catalytic double hydrophosphination of internal alkynes and primary phosphines is possible using a zirconium complex, [κ5-N,N,N,N,C-(Me3SiNCH2CH2)2NCH2CH2NSiMe2CH]Zr (1). The reaction proceeds via stepwise hydrophosphination to give vinyl phosphine products, which can be isolated or further converted to the respective 1,2-bis(phosphino)ethane (i.e., double hydrophosphination). The catalysis is highly selective for formation of secondary phosphine products.

Contrasting protonation behavior of diphosphido vs dithiolato diiron(I) carbonyl complexes

Zaffaroni, Riccardo,Rauchfuss, Thomas B.,Fuller, Amy,De Gioia, Luca,Zampella, Giuseppe

, p. 232 - 238 (2013/02/25)

This paper reports on the protonation of phosphine-substituted diiron diphosphido carbonyls, analogues of diiron dithiolato centers at the active sites of hydrogenase enzymes. Reaction of the diphosphines (CH2) n(PPhH)2 (n = 2 (edpH2) and n = 3 (pdpH 2)) with Fe3(CO)12 gave excellent yields of Fe2(edp)(CO)6 (1) and Fe2(pdp)(CO)6 (2). Substitution of Fe2(edp)(CO)6 with PMe3 afforded Fe2(edp)(CO)2(PMe3)4 (3; νCO 1855 and 1836 cm-1). Crystallographic analysis showed that 3 adopts an idealized C2 symmetry, with pairs of phosphine ligands occupying apical-basal sites on each Fe center. Relative to that in the dithiolato complex, the Fe-Fe bond (2.7786(8) A) is elongated by 0.15 A. Treatment of 3 with H(OEt2)2BAr F4 (ArF = C6H3-3,5- (CF3)2) gave exclusively the C2-symmetric μ-hydride complex [HFe2(edp)(CO)2(PMe3) 4]+. This result contrasts with the behavior of the analogous ethanedithiolate Fe2(edt)(CO)2(PMe 3)4 (edt = 1,2-C2H4S2), protonation of which gives both the bridging and terminal hydride complexes. This difference points to the participation of the sulfur centers in the formation of terminal hydrides. The absence of terminal hydride intermediates was also revealed in the protonation of the diphosphine diphosphido complexes Fe2(pdp)(CO)4(dppv) (4; dppv = cis-1,2-C2H 2(PPh2)2) and Fe2(edp)(CO) 4(dppbz) (5; dppbz = 1,2-C6H4(PPh 2)2). Protonation of these diphosphine complexes afforded μ-hydrido cations with apical-basal diphosphine ligands, which convert to the isomer where the diphosphine is dibasal. In contrast, protonation of the dithiolato complex Fe2(pdt)(CO)4(dppv) gave terminal hydrides, which isomerize to μ-hydrides. In a competition experiment, 4 was shown to protonate faster than Fe2(pdt)(CO)4(dppv).

1,3,6-azadiphosphacycloheptanes: A novel type of heterocyclic diphosphines

Karasik, Andrey A.,Balueva, Anna S.,Moussina, Elvira I.,Naumov, Roman N.,Dobrynin, Alexey B.,Krivolapov, Dmitry B.,Litvinov, Igor A.,Sinyashin, Oleg G.

, p. 125 - 132 (2008/09/18)

The novel type of seven-membered cyclic diphosphines, namely 1,3,6-azadiphosphacycloheptanes, has been synthesized by condensation of 1,2-bis(phenylphosphino)ethane, formaldehyde, and primary amines (aniline, p-toluidine, benzylamine, and 5-aminoisophthalic acid) as a mixture of rac-and meso-stereoisomers. The structures of rac-stereo-isomers of N-tolyl and N-(3′,5′-dicarboxyphenyl)-substituted diphosphines were investigated by X-ray crystal structure analyses. The stereoisomers of N-(3′,5′- dicarboxyphenyl)-substituted compound were separated at a preparative scale, and their platinum(II) dichloride complexes were obtained. The corresponding meso-isomer readily forms P,P-chelate complex with [PtCl2(cod)], whereas the rac-stereoisomer forms oligomeric complex.

Syntheses of new chiral phosphane ligands by diastereoselective conjugate addition of phosphides to enantiomerically pure acceptor-substituted olefins from the chiral pool

Wiese, Burkhard,Knuehl, Guido,Flubacher, Dietmar,Priess, Jan W.,Ulriksen, Bolette,Broedner, Kerstin,Helmchen, Guenter

, p. 3246 - 3262 (2007/10/03)

A variety of new chiral phosphanes were prepared by highly diastereoselective additions of phosphanes to α,β-unsaturated carbonyl compounds and related acceptor-substituted olefins derived from myrtenal as ex chiral pool source. Monophosphanes with astereogenic as well as stereogenic phosphorus are described. In addition diphosphanes were prepared by a highly diastereoselective double conjugate addition of a secondary diphosphane. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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