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693030

Sigma-Aldrich

(S)-T-BINAP

Synonym(s):
(S)-(−)-2,2′-p-tolyl-phosphino)-1,1′-binaphthyl, (S)-Tol-BINAP
Empirical Formula (Hill Notation):
C48H40P2
CAS Number:
Molecular Weight:
678.78
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

optical activity

[α]20/D -156°, c = 0.5 in benzene

mp

250-255 °C

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

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(S)-T-BINAP

Sigma-Aldrich

693030

(S)-T-BINAP

(R)-Tol-BINAP

Sigma-Aldrich

693049

(R)-Tol-BINAP

(R)-DM-BINAP

Sigma-Aldrich

692379

(R)-DM-BINAP

(S,S)-BABIBOP

Sigma-Aldrich

913219

(S,S)-BABIBOP

form

solid

form

solid

form

solid

form

powder

optical activity

[α]20/D -156°, c = 0.5 in benzene

optical activity

[α]20/D +162°, c = 0.5 in benzene

optical activity

[α]20/D +169°, c = 1 in chloroform

optical activity

-

mp

250-255 °C

mp

254-258 °C

mp

187-191 °C

mp

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

(S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO3, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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