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677191

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

96%

Synonym(s):

(2R)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine, (R)-α,α-Diphenylprolinol trimethylsilyl ether

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About This Item

Empirical Formula (Hill Notation):
C20H27NOSi
CAS Number:
943757-71-9
Molecular Weight:
325.52
MDL number:
MFCD09265100
UNSPSC Code:
12352005
PubChem Substance ID:
24885355
NACRES:
NA.22

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assay

96%

form

solid

optical activity

[α]22/D +52±5°, c = 1 in chloroform

refractive index

n20/D 1.5509

density

1.0459 g/mL at 25 °C

functional group

phenyl

storage temp.

2-8°C

SMILES string

C[Si](C)(C)OC([C@H]1CCCN1)(c2ccccc2)c3ccccc3

InChI

1S/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m1/s1

InChI key

RSUHWMSTWSSNOW-LJQANCHMSA-N

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This Item
368199677183677019
(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether 96%

Sigma-Aldrich

677191

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

(S)-(−)-α,α-Diphenyl-2-pyrrolidinemethanol 99%

Sigma-Aldrich

368199

(S)-(−)-α,α-Diphenyl-2-pyrrolidinemethanol

(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether 95%

Sigma-Aldrich

677183

(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether 97%

Sigma-Aldrich

677019

(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether

assay

96%

assay

99%

assay

95%

assay

97%

functional group

phenyl

functional group

hydroxyl, phenyl

functional group

phenyl

functional group

fluoro

form

solid

form

solid

form

-

form

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

optical activity

[α]22/D +52±5°, c = 1 in chloroform

optical activity

[α]20/D −67°, c = 3 in chloroform

optical activity

[α]22/D -50°, c = 1 in chloroform

optical activity

-

density

1.0459 g/mL at 25 °C

density

-

density

1.0459 g/mL at 25 °C

density

-

General description

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether is a diarylprolinol silyl ether organocatalyst.[1]

Application

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether can be used as a catalyst to synthesize:
  • Glycofused tricyclic derivatives, which are used in the development of amyloid β-peptide diagnostic tools.[2]
  • Cyclohexene carbaldehyde derivatives by reacting benzoylnitromethane with aliphatic enals.[3]

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
0000308616
0000240410
0000240429
0000238199
0000238199

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Synthesis and Preliminary Biological Evaluation of Fluorescent Glycofused Tricyclic Derivatives of Amyloid β-Peptide Ligands
D'Orazio G, et al.
European Journal of Organic Chemistry, 2016(9), 1660-1664 (2016)
Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde
David Rodriguez FA, et al.
Journal of Chemistry, 2020 (2020)
The diarylprolinol silyl ether system: a general organocatalyst.
Jensen KL, et al.
Accounts of Chemical Research, 45(2), 248-264 (2011)

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