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14798

Sigma-Aldrich

(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

puriss.

Synonym(s):

(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/REAXYS Number:
5321443
MDL number:
MFCD00010805
UNSPSC Code:
12352005
PubChem Substance ID:
329750625

grade

puriss.

form

solid

optical activity

[α]20/D −239±5°, c = 0.3% in toluene

optical purity

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

238-240 °C (lit.)
238-242 °C (dec.)

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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Application

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

replaced by

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
049264/1
049264/2
045561/1
49264/2
49264/1

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Surojit Bera et al.
Engineering in life sciences, 17(7), 739-748 (2017-03-06)
Various natural polymers with hydrophilic properties have been used to form hydrogels for the encapsulation and delivery of nutrients and drugs in food and pharmaceutical industries. Among them, chitosan (ChiHG)- and alginate (AlgHG)- based hydrogels have been extensively explored for
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.

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