((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium

Base Information

• Chemical Name: ((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium
• CAS No.: 115826-95-4
• Molecular Formula: C₄₄H₃₂Cl₂P₂Pd
• Molecular Weight: 800.012
• European Community (EC) Number: 621-611-4,631-388-5
• Mol file: 115826-95-4.mol

Synonyms:127593-28-6;115826-95-4;((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium;[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride;(S)-BINAP-PdCl2;dichloropalladium;[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;DICHLORO[2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II);[(R)-(+)-2,2/'-BIS(DIPHENYLPHOSPHINO)-1,1/'-BINAPHTHYL]PALLADIUM(II) CHLORIDE;DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II);MFCD00075254;(R)-(+)-(2,2-Bis(Diphenylphosphino)-1,1-binaphthyl)palladium(II)chloride;[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II)chloride;Dichloro[(S)-()-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II);DICHLORO[(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II);Dichloro[(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II), min. 98%;2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYLPALLADIUM(II) CHLORIDE;SCHEMBL365531;VDHAUMFISVWIRX-UHFFFAOYSA-L;AKOS015914422;AT37026;SC10441;FT-0696080;FT-0696081;F10282;Dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II), 97%;[(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride, 97%;Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II), 97%;PALLADIUM, [(1S)-[1,1'-BINAPHTHALENE]-2,2'-DIYLBIS[DIPHENYLPHOSPHINE-KAPPAP]]DICHLORO-, (SP-4-2)-

Chemical Property of ((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium

Chemical Property:

• Appearance/Colour: brown-black crystals
• Melting Point: 106-108°C(lit.)
• Boiling Point: 724.3 °C at 760 mmHg
• Flash Point: 419 °C
• PSA: 27.18000
• LogP: 10.55540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 798.03911
• Heavy Atom Count: 49
• Complexity: 800

Purity/Quality:

>98%,Pd13.3 ^*data from raw suppliers

((R)-2,2''-Bis(diphenylphosphino)-1,1''-binaphthyl)dichloropalladium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.Cl[Pd]Cl
• Uses: ((R)-2,2''-Bis(diphenylphosphino)-1,1''-binaphthyl)dichloropalladium can be used as a catalyst.

Technology Process of ((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium

There total 11 articles about ((S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl)dichloropalladium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

dichloro bis(acetonitrile) palladium(II) (21264-30-2,90243-59-7,14592-56-4) + (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) (76144-87-1,76189-55-4,76189-56-5,98327-87-8,136655-44-2) → [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride (115826-95-4,127593-28-6,253157-79-8)

Guidance literature:

In benzene; at 20 ℃; for 2h;

Reference yield: 97.0%

dichloro(1,5-cyclooctadiene)palladium(II) (12107-56-1) + (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) (76144-87-1,76189-55-4,76189-56-5,98327-87-8,136655-44-2) → [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) chloride (115826-95-4,127593-28-6,253157-79-8)

Guidance literature:

DOI:10.1016/j.poly.2012.11.016

Reference yield: 91.0%

dichloro bis(acetonitrile) palladium(II) (21264-30-2,90243-59-7,14592-56-4) + (R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene (76189-55-4,76189-56-5,98327-87-8) → [(R)-(+)-1,1‘-binaphthalene-2,2’-diylbis(diphenylphosphane)]palladium(II)chloride (127593-28-6,115826-95-4,253157-79-8)

Guidance literature:

With Et₂O; (N2); heating, refluxing (3 day), concentration; filtration, washing (Et2O), drying (vac.); elem. anal.;

DOI:10.1016/S1381-1169(98)00299-4

upstream raw materials:

dichloro bis(acetonitrile) palladium(II)

(S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine)

dichloro(1,5-cyclooctadiene)palladium(II)

(R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene

Downstream raw materials:

Pd(C₆H₅)2PC₂₀H₁₂P(C₆H₅)2(SO₃CF₃)⁽¹⁺⁾*CF₃SO₃^(1-)=Pd((C₆H₅)2PC₂₀H₁₂P(C₆H₅)2)(SO₃CF₃)2

Refernces

• 1、 Ozawa, Fumiyuki,Kubo, Akihiko,Matsumoto, Yonetatsu,Hayashi, Tamio,Nishioka, Eriko,Yanagi, Kazunori,Moriguchi, Koh-Ichi. "Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution process". . p. 4188 - 4196. Retrieved 1993.
• 2、 Graaf, Wim de,Boersma, Jaap,Koten, Gerard van,Elsevier, Cornelis J.. "Chiral induction in the synthesis of 4,4-dimethyl-1-phenylpenta-1,2-diene (1-Ph-3-t-Bu-allene) catalyzed by chiral phosphine complexes of palladium". . p. 115 - 124. Retrieved 1989.
• 3、 Pomarański, Piotr,Samanta, Sauvik,Roszkowski, Piotr,Maurin, Jan K.,Czarnocki, Zbigniew. "Enantioselective synthesis of axially chiral 3-bromo-4-alkoxy-2,6-dimethyl-5-(naphthalen-1-yl)pyridines via an asymmetric Suzuki–Miyaura cross-coupling reaction". . p. 4713 - 4717. Retrieved 2016.
• 4、 Yamamoto,Matsui,Okajima,Karuppuchamy,Yoshihara. "Electronic behavior of calcined material obtained from 2,2-diphenylphosphino-1,1-binaphthyldichloro palladium". . p. 274 - 278. Retrieved 2008.
• 5、 Doherty, Simon,Knight, Julian G.,Smyth, Catherine H.,Harrington, Ross W.,Clegg, William. "Metal-dependent reactivity of electrophilic platinum group metal lewis acid catalysts: Competitive alkene dimerization, intramolecular friedel-crafts alkylation, and carbonyl-ene reactivity". . p. 5961 - 5966. Retrieved 2007.