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Key Documents

668982

Sigma-Aldrich

2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

97%

Synonym(s):

rac-Tol-BINAP

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About This Item

Empirical Formula (Hill Notation):
C48H40P2
CAS Number:
Molecular Weight:
678.78
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:

assay

97%

reaction suitability

reagent type: ligand

mp

267-271 °C

functional group

phosphine

SMILES string

Cc1ccc(cc1)P(c2ccc(C)cc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccc(C)cc7)c8ccc(C)cc8

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

InChI key

IOPQYDKQISFMJI-UHFFFAOYSA-N

Application

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

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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