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693022

Sigma-Aldrich

(S)-DM-BINAP

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Synonym(s):
(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
Empirical Formula (Hill Notation):
C52H48P2
CAS Number:
135139-00-3
Molecular Weight:
734.89
MDL number:
MFCD01630821
UNSPSC Code:
12352005
PubChem Substance ID:
329761554

form

solid

optical activity

[α]/D -172°, 20, c = 1 in chloroform

mp

189-193 °C

SMILES string

Cc1cc(C)cc(c1)P(c2cc(C)cc(C)c2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7cc(C)cc(C)c7)c8cc(C)cc(C)c8

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

InChI key

MXGXXBYVDMVJAO-UHFFFAOYSA-N

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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

Legal Information

Sold in collaboration with Takasago for research purposes only.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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