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677213

Sigma-Aldrich

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

technical grade

Synonym(s):

(R)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether, (R)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)]trimethylsilanyloxy)methyl]pyrrolidine, (R)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)]trimethylsilyloxy)methyl]pyrrolidine

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About This Item

Empirical Formula (Hill Notation):
C24H23F12NOSi
CAS Number:
908303-26-4
Molecular Weight:
597.51
MDL number:
MFCD09750448
UNSPSC Code:
12352005
PubChem Substance ID:
24885357
NACRES:
NA.22

grade

technical grade

optical purity

enantiomeric excess: ≥99.0% (HPLC)

mp

46-55 °C

SMILES string

C[Si](C)(C)OC([C@H]1CCCN1)(c2cc(cc(c2)C(F)(F)F)C(F)(F)F)c3cc(cc(c3)C(F)(F)F)C(F)(F)F

InChI

1S/C24H23F12NOSi/c1-39(2,3)38-20(19-5-4-6-37-19,13-7-15(21(25,26)27)11-16(8-13)22(28,29)30)14-9-17(23(31,32)33)12-18(10-14)24(34,35)36/h7-12,19,37H,4-6H2,1-3H3/t19-/m1/s1

InChI key

MOHRGTBNEJKFMB-LJQANCHMSA-N

Related Categories

Application

Catalyst involved in:
  • Cyclocondensation of enals with methylenepyrrolidines
  • Organocatalytic additions of β-ketosulfoxides to conjugated aldehydes
  • Organocatalytic aza-Michael reactions
  • Stereoselective propargylic alkylation of propargylic esters with aldehydes
  • Epoxidation or aziridination of α,β-unsaturated aldehydes and Feist-Benary reactions of 1,3-dicarbonyls

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)

>230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Articles

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Professor Karl Anker Jørgensen and his group have developed ethers which serve as excellent chiral organocatalysts in the direct asymmetric α-functionalization of aldehydes.

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