(1-{2-[bis(3,5-dimethylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(3,5-dimethylphenyl)phosphane

• ChemBase ID: 135873
• Molecular Formular: C52H48P2
• Molecular Mass: 734.885042
• Monoisotopic Mass: 734.3231248
• SMILES: Cc1cc(cc(c1)P(c1ccc2ccccc2c1c1c2ccccc2ccc1P(c1cc(cc(c1)C)C)c1cc(cc(c1)C)C)c1cc(cc(c1)C)C)C
• Canonical SMILES: Cc1cc(C)cc(c1)P(c1ccc2c(c1c1c(ccc3c1cccc3)P(c1cc(C)cc(c1)C)c1cc(C)cc(c1)C)cccc2)c1cc(C)cc(c1)C
• InChI: InChI=1S/C52H48P2/c1-33-21-34(2)26-43(25-33)53(44-27-35(3)22-36(4)28-44)49-19-17-41-13-9-11-15-47(41)51(49)52-48-16-12-10-14-42(48)18-20-50(52)54(45-29-37(5)23-38(6)30-45)46-31-39(7)24-40(8)32-46/h9-32H,1-8H3
• InChIKey: MXGXXBYVDMVJAO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1-{2-[bis(3,5-dimethylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(3,5-dimethylphenyl)phosphane
• IUPAC Traditional name: (1-{2-[bis(3,5-dimethylphenyl)phosphanyl]naphthalen-1-yl}naphthalen-2-yl)bis(3,5-dimethylphenyl)phosphane
• Synonyms: 2,2′-Bis[bis(3,5-dimethylphenyl)phosphino]-1,1′-binaphthyl; 2,2′-Bis[di(3,5-xylyl)phoshino]-1,1′-binaphthyl; 3,5-Xylyl-BINAP; DM-BINAP; (S)-Xylyl-BINAP; (S)-(-)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl; (R)-Xylyl-BINAP; (R)-(+)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl; (S)-(-)-2,2′-Bis[bis(3,5-dimethylphenyl)phosphino]-1,1′-binaphthyl; (S)-(-)-2,2′-Bis[di(3,5-xylyl)phoshino]-1,1′-binaphthyl; (S)-3,5-Xylyl-BINAP; (S)-DM-BINAP; (R)-(+)-1,1′-Binaphthalene-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine]; (R)-(+)-2,2′-Bis[di(3,5-xylyl)phosphino]-1,1′-binaphthyl; (R)-DM-BINAP; 1,1'-联萘-2,2'-双二(3,5-二甲苯基)膦; 2,2′-双[二(3,5-二甲苯基)膦]-1,1′-联萘; 联萘(3,5-二甲苯基)膦; (S)-(-)-2,2'-二(二-3,5-二甲基苯基)膦-1,1'-联萘; (R)-(+)-2,2'-二(二-3,5-甲基苯基膦)-1,1'-联萘; (S)-联萘(3,5-二甲苯基)膦; (S)-(-)-2,2′-双[二(3,5-二甲苯基)膦]-1,1′-联萘; (R)-(+)-1,1′-联萘-2,2′-二基)二[双(3,5-二甲基苯基)膦]; (R)-(+)-2,2′-双[二(3,5-二甲苯基)膦]-1,1′-联萘

Database IDs

• CAS Number: 145416-77-9; 135139-00-3; 137219-86-4
• MDL Number: MFCD01630821
• PubChem SID: 162230144
• PubChem CID: 4189905

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 15.593
• LogD (pH = 7.4): 15.593
• Log P: 15.593
• Molar Refractivity: 235.554 cm^3
• Polarizability: 94.75567 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 187-191 °C; 189-193 °C; 201-203°C; 257-262 °C
• Optical Rotation: [α]/D -172°, 20, c = 1 in chloroform; [α]20/D +169°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C52H48P2

DETAILS

Sigma Aldrich - 693022

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Catalyst for:
• Asymmetric hydrogenation of benzophenone
• Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives in the presence of chiral biaryl bisphosphine ligands
• Regiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolates
• Ligand controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids to form regioisomeric arylcyclopentenols
• Platinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperature
• Stereoselective preparation of chiral N,O-biaryls via Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes

Sigma Aldrich - 692379

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions