(1-{2-[bis(4-methylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(4-methylphenyl)phosphane

• ChemBase ID: 135664
• Molecular Formular: C48H40P2
• Molecular Mass: 678.778722
• Monoisotopic Mass: 678.26052454
• SMILES: Cc1ccc(cc1)P(c1ccc(cc1)C)c1ccc2ccccc2c1c1c2ccccc2ccc1P(c1ccc(cc1)C)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1ccc(cc1)C)c1ccc(cc1)C)cccc2)c1ccc(cc1)C
• InChI: InChI=1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3
• InChIKey: IOPQYDKQISFMJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1-{2-[bis(4-methylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(4-methylphenyl)phosphane
• IUPAC Traditional name: (1-{2-[bis(4-methylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(4-methylphenyl)phosphane
• Synonyms: rac-Tol-BINAP; 2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl; (S)-(-)-2,2′-p-tolyl-phosphino)-1,1′-binaphthyl; (S)-T-BINAP; (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl; (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl; rac-p-Tol-BINAP; (±)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl; (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl; (S)-Tol-BINAP; (S)-(-)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl; (R)-Tol-BINAP; (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl; (R)-T-BINAP; 2,2′-双(二对甲苯基膦)-1,1′-联萘; (S)-(-)-2,2′-双(二对甲苯基膦)-1,1'-二联萘; (R)-(+)-2,2'-双(二-4-甲基苯基膦)-1,1'-联萘; (S)-(+)-2,2'-双(二-4-甲基苯基膦)-1,1'-联萘; (+/-)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘; (R)-(+)-2,2′-双(二-对甲苯基膦)-1,1′-联萘; (S)-(-)-2,2′-双(二-对甲苯基膦)-1,1′-联萘; (R)-(+)-2,2′-双(二-对甲苯基膦)-1,1′-联萘

Database IDs

• CAS Number: 100165-88-6; 153305-67-0; 99646-28-3
• MDL Number: MFCD01311709; MFCD00269856
• PubChem SID: 24885012; 24885013; 162229937; 24885011
• PubChem CID: 4189906

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 13.7242
• LogD (pH = 7.4): 13.7242
• Log P: 13.7242
• Molar Refractivity: 215.3892 cm^3
• Polarizability: 87.70807 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 250-255 °C; 252-256 °C; 254-258 °C; 255-257°C; 267-271 °C; 267-271°C
• Optical Rotation: [α]20/D +162°, c = 0.5 in benzene; [α]20/D -156°, c = 0.5 in benzene; +156 (c=0.5 in benzene)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C48H40P2

DETAILS

Sigma Aldrich - 668982

Application
Used in:
• Rhodium-catalyzed 2+2+2 cycloaddition reactions1
• Decarboxylative coupling of carboxylic acids using copper-palladium-phenanthroline-Tol-BINAP catalyst system2
• Palladium-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions3
• Preparation of methylenesultams via intramolecular Heck cyclization of bromovinylsulfonamides and subsequent Michael addition reaction of sultams with thiols4
• Regioselective intermolecular cyclotrimerization of alkynes in complex with cationic rhodium(I)5
• Palladium-catalyzed amination reactions6
• Palladium-catalyzed ether formation from aryl halides7

Sigma Aldrich - 693049

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
Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated esterReactant serving as a precursor for:
• Catalysts used for reductive amination of ketones
• Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives
• Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones
• CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters
• BINAP Pt Dications for cation trapping

Sigma Aldrich - 668966

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated ester1Reactant serving as a precursor for:
• Catalysts used for reductive amination of ketones2
• Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives3
• Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones4
• CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters5
• BINAP Pt Dications for cation trapping6

Sigma Aldrich - 668974

Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 693030

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