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

• ChemBase ID: 69483
• Molecular Formular: C44H32P2
• Molecular Mass: 622.672402
• Monoisotopic Mass: 622.19792428
• SMILES: c1(c(ccc2ccccc12)P(c1ccccc1)c1ccccc1)c1c(ccc2ccccc12)P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccccc1)c1ccccc1)cccc2)c1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane
• IUPAC Traditional name: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane; binap
• Synonyms: (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (±)-BINAP; [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine]; (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; 1,1'-[(1R)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine; (+)-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene; (R)-BINAP; 1,1'-[(1S)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine; (1S)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (S)-BINAP; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (+/-)-BINAP; (+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine); (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; rac-BINAP; (+/-)-2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl 98%; (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (R)-(+)-BINAP; (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl; (R)-BINAP; (S)-(-)-BINAP; (S)-(-)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene; (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl; (S)-BINAP; BINAP; BINAP; (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘; (±)-2,2′-双(二苯基膦)-1,1′-联萘; 2,2′-双(二苯基膦)-1,1′-联萘; (±)-2,2′-双(二苯基膦)-1,1′-联萘; (+/-)-2,2'-双(二苯基膦基)-1,1'-联萘; (S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘; (R)-(+)-(1,1′-联萘-2,2′-二基)双(二苯膦); (R)-(+)-2,2′-双(二苯基膦)-1,1′-联萘; (S)-(-)-1,1′-联萘-2,2'-双二苯膦; (S)-(-)-2,2′-双(二苯膦基)-1,1′-联萘; (S)-(-)-2,2'-Bis(双二苯基磷)-1,1'-双萘; (R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘

Database IDs

• CAS Number: 98327-87-8; 76189-55-4; 76189-56-5
• EC Number: None
• MDL Number: MFCD00010805
• Beilstein Number: 5321443; 4914063; 5321444
• Merck Index: 141223
• PubChem SID: 24848870; 24848869; 162035209; 24857814; 24857815; 24871738; 24850475
• PubChem CID: 634876
• Chemspider ID: 551072
• Wikipedia Title: BINAP

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 11.8554
• LogD (pH = 7.4): 11.8554
• Log P: 11.8554
• Molar Refractivity: 195.2244 cm^3
• Polarizability: 80.66715 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; organic solvents
• Apperance: Beige Solid; colorless solid; Off-White Solid
• Melting Point: 223-225°C; 228-230°C; 238-240 °C(lit.); 238-242 °C (dec.); 239-241 °C(lit.); 239-241 °C (R); 238-240 °C (S); 239-241°C; 281-285°C; 283-286 °C(lit.); 283-286°C
• Optical Rotation: [α]19/D +233°, c = 0.3 in toluene; [α]19/D -233°, c = 0.3 in toluene; [α]20/D +222°, c = 0.5% in benzene; [α]20/D +239±5°, c = 0.3% in toluene; [α]20/D -222, c = 0.5 in benzene; [α]20/D -239±5°, c = 0.3% in toluene; +230 (c=0.3 in toluene); -230 (c=0.3 in toluene)
• Ligand For: Acylations; Arylations; Buchwald-Hartwig Cross Coupling Reaction; C-C Bond Formation; Decarboxylations; Stille Coupling

Safety Information

• Storage Condition: Amber Vial, Refrigerator
• Storage Warning: Air Sensitive; IRRITANT; Irritant/Air Sensitive/Light Sensitive/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280G-P305+P351+P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 97%; 98%
• Grade: puriss.
• Optical Purity: ee: 99% (HPLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Linear Formula: [(C6H5)2PC10H6-]2
• Empirical Formula (Hill Notation): C44H32P2

DETAILS

Apollo Scientific Ltd - OR18264

Racemic mixture

Sigma Aldrich - 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

Sigma Aldrich - 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

Sigma Aldrich - 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

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

Sigma Aldrich - 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

Sigma Aldrich - 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

Sigma Aldrich - 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

Toronto Research Chemicals - B386850

Chiral ligand for metal mediated asymmetric catalysis.

Toronto Research Chemicals - B386851

Chiral ligand for metal mediated asymmetric catalysis.

REFERENCES

• Ito, H., et al.: Nat. Chem., 2, 972 (2010)
• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (2010)
• Inui, Y., et al.: Chem. Pharm. Bull., 57, 1158 (2009)
• Lam, K., et al.: Eur. J. Med. Chem., 45, 5527 (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).
• 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).
• See also previous entry.
• 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).
• 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).