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693057

Sigma-Aldrich

(S)-BINAP

Synonym(s):

(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (S)-(−)-BINAP

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About This Item

Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
76189-56-5
Molecular Weight:
622.67
Beilstein:
5321443
MDL number:
MFCD00010805
UNSPSC Code:
12352005
PubChem Substance ID:
329761558
NACRES:
NA.22

form

crystals

optical activity

[α]20/D -222, c = 0.5 in benzene

mp

238-240 °C (lit.)

InChI

1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

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Related Categories

Application

Takasago Ligands and Complexes for Asymmetric Reactions
Reactant involved in:
  • Enantioselective and diastereoselective unpoled carbonyl allylation
  • Syntehsis of organophophine oxides as anittumor agents
  • SN2 halogenation of hydroxy groups
  • Synthesis of BINAP complexes
  • Studies of conformational flexibility of BINAP chelates

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

693057-100MG:
693057-BULK:
693057-VAR:
693057-500MG:

Certificates of Analysis (COA)

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Kim-Hung Lam et al.
European journal of medicinal chemistry, 45(11), 5527-5530 (2010-09-14)
Following our previously reported pyridinyl phosphine oxides as antitumor agents, we targeted the commercially available C(2)-axial chiral organophosphine ligand catalysts, such as 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) 1 and 2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine (P-Phos) 2 as a convenient source for producing organophosphine oxides as antitumor leads.

Articles

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

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