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569763

Sigma-Aldrich

(5S)-(−)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochloride

97%

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About This Item

Empirical Formula (Hill Notation):
C13H18N2O · HCl
CAS Number:
Molecular Weight:
254.76
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

optical activity

[α]20/D -67°, c = 1 in H2O

mp

157-161 °C (lit.)

SMILES string

Cl.CN1C(=O)[C@H](Cc2ccccc2)NC1(C)C

InChI

1S/C13H18N2O.ClH/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10;/h4-8,11,14H,9H2,1-3H3;1H/t11-;/m0./s1

InChI key

YIYFEXGDFJLJGM-MERQFXBCSA-N

Application

Metal-free OrganoCatalyst technology for asymmetric catalysis. Catalyzes asymmetric Diels-Alder reactions, 1,3-dipolar additions and pyrrole alkylations in high enantiomeric excess.
Used in first highly enantioselective organocatalytic Diels-Alder reaction and 1,3-dipolar addition.

Legal Information

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

Storage Class Code

13 - Non 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ahrendt, K. A. et al
Journal of the American Chemical Society, 122, 4243-4243 (2000)
New strategies in organic catalysis: the first enantioselective organocatalytic Friedel-Crafts alkylation.
N A Paras et al.
Journal of the American Chemical Society, 123(18), 4370-4371 (2001-07-18)
Jen, W. S. et al
Journal of the American Chemical Society, 122, 9874-9874 (2000)

Articles

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

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