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674745

Sigma-Aldrich

(R)-(–)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

95%

Synonym(s):

(11bR)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d:1′,2′f]-1,3,2-dioxaphosphepin 4-oxide, MacMillan TiPSY catalyst

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About This Item

Empirical Formula (Hill Notation):
C56H41O4PSi2
CAS Number:
791616-55-2
Molecular Weight:
865.07
MDL number:
MFCD09265079
UNSPSC Code:
12352005
PubChem Substance ID:
24885235
NACRES:
NA.22

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Quality Level

100

assay

95%

form

solid

optical activity

[α]22/D -197°, c = 1 in chloroform

mp

329-335 °C

functional group

phosphate

SMILES string

OP1(=O)Oc2c(cc3ccccc3c2-c4c(O1)c(cc5ccccc45)[Si](c6ccccc6)(c7ccccc7)c8ccccc8)[Si](c9ccccc9)(c%10ccccc%10)c%11ccccc%11

InChI

1S/C56H41O4PSi2/c57-61(58)59-55-51(62(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)60-61)63(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40H,(H,57,58)

InChI key

BDQOCXQVIFQJRK-UHFFFAOYSA-N

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1 of 4

This Item
680184248932248940
(R)-(–)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 95%

Sigma-Aldrich

674745

(R)-(–)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

(S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 96%

Sigma-Aldrich

680184

(S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate ≥98%

Sigma-Aldrich

248932

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

(S)-(+)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate 97%

Sigma-Aldrich

248940

(S)-(+)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

assay

95%

assay

96%

assay

≥98%

assay

97%

form

solid

form

solid

form

solid

form

solid

functional group

phosphate

functional group

phosphate

functional group

phosphate

functional group

phosphate

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

329-335 °C

mp

188-193 °C

mp

-

mp

-

optical activity

[α]22/D -197°, c = 1 in chloroform

optical activity

[α]22/D +210°, c = 1 in chloroform

optical activity

[α]20/D −605°, c = 1.35 in methanol

optical activity

[α]22/D +595°, c = 1.35 in methanol

Application

Organocatalyst for the first enatioselective organocatalytic reductive amination reaction.[1]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - 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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Certificates of Analysis (COA)

Lot/Batch Number
MKCT1026
MKCN8800
MKCD2114
MKBW5264V
07122KH

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R Ian Storer et al.
Journal of the American Chemical Society, 128(1), 84-86 (2006-01-05)
The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines and provided a highly stereoselective method for the

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