CAS 76189-56-5|CAS 98327-87-8|CAS 76189-55-4|{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane|2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl|{1-[2-(diphenylphosphanyl)naphtha...

General Information

Structure

Molecular Formula

C₄₄H₃₂P₂

Molecular Mass

622.672402

Exact Mass

622.19792428

Charge

InChI

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

InChIKey

MUALRAIOVNYAIW-UHFFFAOYSA-N

Canonic Smiles

c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1

Isomeric Smiles

c1(c(ccc2ccccc12)P(c1ccccc1)c1ccccc1)c1c(ccc2ccccc12)P(c1ccccc1)c1ccccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

11.8554

LogD (pH = 7.4)

11.8554

Log P

11.8554

Molar Refractivity

195.2244

Polarizability

80.66715

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

IUPAC name

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane

Synonyms

2,2'-Bis(diphenylphosphino)-1,1'-binaphthylrac-BINAP(+/-)-2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl 98%(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl[1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine](R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthaleneBINAP(R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘(R)-BINAP(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl(S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘(S)-(-)-BINAP(R)-(+)-BINAP2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(±)-BINAPBINAP(S)-(-)-1,1′-联萘-2,2'-双二苯膦(S)-BINAP(±)-2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-(1,1′-联萘-2,2′-二基)双(二苯膦)(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(S)-(-)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene(±)-2,2′-双(二苯基膦)-1,1′-联萘(R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘(+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine)(±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]1,1'-[(1S)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(双二苯基磷)-1,1'-双萘(+/-)-BINAP(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene1,1'-[(1R)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine(+/-)-2,2'-双(二苯基膦基)-1,1'-联萘(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-BINAP(+)-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine](S)-BINAP(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene

IUPAC Traditional name

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane binap

Names and Identifiers

Registration numbers

MDL Number

MFCD00010805

Beilstein Number

532144349140635321444

PubChem SID

162035209248578142485047524848869248488702485781524871738

PubChem CID

634876

CAS Number

76189-56-598327-87-876189-55-4

Merck Index

EC Number

Chemspider ID

Wikipedia Title

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Apollo Scientific

OR18264

Racemic mixture

Wikipedia

BINAP

Sigma Aldrich

693065

Packaging
100, 500 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions

693057

Packaging
100, 500 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
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

295817

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application
Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation1 and disilylation.2 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones,3 β-keto esters,4 and α-amino ketones.5 They have also been used for asymmetric hydrogenation6 and hydroformylation of olefins,7 asymmetric Heck reactions,8 and asymmetric isomerizations of allyls.9,10Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes.11 Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.12

295825

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application
2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones,1 β-keto esters,2 and α-amino ketones.3 They have also been used for asymmetric hydrogenation4 and hydroformylation of olefins,5 asymmetric Heck reactions,6 and asymmetric isomerizations of allyls.7,8Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.
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

481084

Application
Ligand employed in a palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.1 Used with Cu (II) to catalyze addition of arylsulfonamides to styrenes and olefins.2 Amination of terpyridines with Pd catalysis.3
General description
Racemic version of BINAP.4
Packaging
5, 25, 100 g in glass bottle

14798

Application
Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation1
• Syntehsis of organophophine oxides as anittumor agents2
• SN2 halogenation of hydroxy groups3
• Synthesis of BINAP complexes4,5
• Studies of conformational flexibility of BINAP chelates6

14797

Other Notes
Chiral atropisomeric diphosphine; the rhodium and ruthenium complexes are employed for asymmetric hydrogenation and isomerization reactions 1,2,3; Preparation of BINAP-ruthenium dicarboxylate complexes 4

TRC

B386851

Chiral ligand for metal mediated asymmetric catalysis.

B386850

Chiral ligand for metal mediated asymmetric catalysis.

Molecule Details

References

PubChem Literature

From Data Sources

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2009)

• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)

• Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).

• Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ?-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).

• For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).

• See also previous entry.

• The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane

Synonyms

IUPAC Traditional name

{1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane binap

Registration numbers

MDL Number

MFCD00010805

Beilstein Number

532144349140635321444

PubChem SID

162035209248578142485047524848869248488702485781524871738

PubChem CID

634876

CAS Number

76189-56-598327-87-876189-55-4

Merck Index

EC Number

Chemspider ID

Wikipedia Title

Properties

Molecule Details

Apollo Scientific

OR18264

Racemic mixture

Wikipedia

BINAP

Sigma Aldrich

693065

Packaging
100, 500 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions

693057

295817

295825

481084

14798

14797

TRC

B386851

Chiral ligand for metal mediated asymmetric catalysis.

B386850

Chiral ligand for metal mediated asymmetric catalysis.

References

PubChem Literature

From Data Sources

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)

• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2009)

• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)

• For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999).

• See also previous entry.

• The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998).

Bioactivity

PubChem BioAssay

Molecule

ID:69483