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674605

Sigma-Aldrich

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

95%

Synonym(s):

(11bR)-2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-4-hydroxydinaphtho[2,1-d:1′,2′-f]-1,3,2-dioxaphosphepin 4-oxide, (R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-bi-2-naphthol cyclic monophosphate

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About This Item

Empirical Formula (Hill Notation):
C36H17F12O4P
CAS Number:
791616-62-1
Molecular Weight:
772.47
UNSPSC Code:
12352101
PubChem Substance ID:
24885225
NACRES:
NA.22

Quality Level

100

assay

95%

form

solid

optical activity

[α]20/D -220°, c = 1 in chloroform (typical)

mp

162-175 °C

SMILES string

OP1(=O)Oc2c(cc3ccccc3c2-c4c(O1)c(cc5ccccc45)-c6cc(cc(c6)C(F)(F)F)C(F)(F)F)-c7cc(cc(c7)C(F)(F)F)C(F)(F)F

InChI

1S/C36H17F12O4P/c37-33(38,39)21-9-19(10-22(15-21)34(40,41)42)27-13-17-5-1-3-7-25(17)29-30-26-8-4-2-6-18(26)14-28(32(30)52-53(49,50)51-31(27)29)20-11-23(35(43,44)45)16-24(12-20)36(46,47)48/h1-16H,(H,49,50)

InChI key

DQORDVSQWPKAQJ-UHFFFAOYSA-N

Related Categories

General description

(R)-3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate is a BINOL-based chiral phosphoric acid, which can efficiently catalyze the nucleophilic addition to imine substrates. [BINOL=1,1′-bi-2-naphthol]

Application

As a chiral Bronsted acid, BINOL- derived cyclic phosphoric acid (such as Akiyama chiral Bronsted acid) was also shown to be an efficient catalyst for the hydrophosphonylation of aldimines at room temperature.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Takahiko Akiyama et al.
Organic letters, 7(13), 2583-2585 (2005-06-17)
[reaction: see text] A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Brønsted acid (10 mol %) in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature. Alpha-amino phosphonates were obtained with good to high enantioselectivities.

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