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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

Assay

95%

form

solid

optical activity

[α]22/D -197°, c = 1 in chloroform

mp

329-335 °C

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

Application

Organocatalyst for the first enatioselective organocatalytic reductive amination reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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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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