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663085

Sigma-Aldrich

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

97%

Synonym(s):

(5S)-2,2,3-Trimethyl-5-phenylmethyl-4-imidazolidinone dichloroacetic acid

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About This Item

Empirical Formula (Hill Notation):
C15H20Cl2N2O3
CAS Number:
345358-20-5
Molecular Weight:
347.24
MDL number:
MFCD08276841
UNSPSC Code:
12352005
PubChem Substance ID:
24884183
NACRES:
NA.22

Assay

97%

mp

122-126 °C

SMILES string

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

InChI

1S/C13H18N2O.C2H2Cl2O2/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10;3-1(4)2(5)6/h4-8,11,14H,9H2,1-3H3;1H,(H,5,6)/t11-;/m0./s1

InChI key

YZRAPAXOLQHZSE-MERQFXBCSA-N

Application

Utilized in the first example of organocatalytic enantioselective α-fluorination of aldehydes.

Legal Information

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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

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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Teresa D Beeson et al.
Journal of the American Chemical Society, 127(24), 8826-8828 (2005-06-16)
The first direct enantioselective catalytic alpha-fluorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective fluorination of aldehydes to generate alpha-fluoro aldehydes, an important chiral synthon for medicinal agent synthesis.

Articles

Macmillan Imidazolidinone Organocatalysts

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

Macmillan Imidazolidinone Organocatalysts

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

Macmillan Imidazolidinone Organocatalysts

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

Macmillan Imidazolidinone Organocatalysts

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

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