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Sigma-Aldrich

(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol

≥99% (HPLC)

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Synonym(s):
(S)-(−)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine
Empirical Formula (Hill Notation):
C21H27NO
CAS Number:
Molecular Weight:
309.45
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

≥99% (HPLC)

optical purity

enantiomeric ratio: 97.5% (HPLC)

mp

98-101 °C

storage temp.

2-8°C

SMILES string

Cc1cc(C)cc(c1)C(O)([C@@H]2CCCN2)c3cc(C)cc(C)c3

InChI

1S/C21H27NO/c1-14-8-15(2)11-18(10-14)21(23,20-6-5-7-22-20)19-12-16(3)9-17(4)13-19/h8-13,20,22-23H,5-7H2,1-4H3/t20-/m0/s1

InChI key

MXIOBZPVLNQGIU-FQEVSTJZSA-N

Application

(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol can be used as:
  • A chiral organocatalyst in the preparation of α-[(phenyl)methyl]thio]alkanal derivatives using aldehydes as starting materials and [(phenyl)methyl]thio]triazole as a sulfur electrophile.
  • A catalyst in the preparation of chiral bipyrazolidin-3-one derivatives by cycloadditions of azomethine imines with α,β-unsaturated aldehydes.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Diarylprolinol silyl ether salts as new, efficient, water-soluble, and recyclable organocatalysts for the asymmetric Michael addition on water
Zheng Z, et al.
Journal of the American Chemical Society, 132(1), 50-51 (2010)
Enantioselective organocatalyzed alpha sulfenylation of aldehydes.
Mauro Marigo et al.
Angewandte Chemie (International ed. in English), 44(5), 794-797 (2005-01-20)

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