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Merck
CN

569763

(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:
278173-23-2
Molecular Weight:
254.76
NACRES:
NA.22
PubChem Substance ID:
24880521
UNSPSC Code:
12352005
MDL number:
MFCD03426983

Key Documents

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Product Name

(5S)-(−)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochloride, 97%

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

SMILES string

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

InChI key

YIYFEXGDFJLJGM-MERQFXBCSA-N

assay

97%

form

solid

optical activity

[α]20/D -67°, c = 1 in H2O

mp

157-161 °C (lit.)

functional group

phenyl

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

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG5399
MKBX2103V
MKBR9626V
MKBH6360V
MKBG9282V

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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

Macmillan Imidazolidinone Organocatalysts

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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