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Sigma-Aldrich

2-Imidazolidone

96%

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Synonym(s):
2-Oxoimidazolidine, N,N′-Ethyleneurea
Empirical Formula (Hill Notation):
C3H6N2O
CAS Number:
120-93-4
Molecular Weight:
86.09
Beilstein:
106252
EC Number:
204-436-4
MDL number:
MFCD00005257
PubChem Substance ID:
24896082
NACRES:
NA.22

Assay

96%

mp

129-132 °C (lit.)

SMILES string

O=C1NCCN1

InChI

1S/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)

InChI key

YAMHXTCMCPHKLN-UHFFFAOYSA-N

Gene Information

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Application

Reactant for synthesis of:
  • Chiral microporous materials from achiral precursors
  • Aryl and heteroaryl N-acylureas via microwave-assisted palladium-catalyzed carbonylation
  • A highly water-soluble peptide based human neutrophil elastase inhibitor
  • Heterocycles by cyanoacetylation for antimicrobial use

Reactant for:
  • Pd-catalyzed C-N bond formation with heteroaromatic tosylates
  • Oxidative amidation of activated alkenes

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Statements

H319 - H373

Hazard Classifications

Eye Irrit. 2 - STOT RE 2

Target Organs

Thyroid

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Mette L H Mantel et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(18), 5437-5442 (2010-04-09)
A protocol for the palladium(0)-catalyzed amidation of heteroaromatic tosylates was successfully developed. The methodology proved to be effective for a variety of heteroaryl tosylates including the pyridine, pyrimidine, quinoline and quinoxaline ring systems. Successful carbon-nitrogen bond formation with these heteroaryl
Synthesis and antimicrobial activity of new heterocycles obtained using cyanoacetylation
Sh. M. Abu-Bakr, et al.,
Pharmaceutical Chemistry Journal, 44, 433-437 (2010)
New Synthesis of Aryl and Heteroaryl N-Acylureas via Microwave-Assisted Palladium-Catalyzed Carbonylation
D. Liptrot, et al.,
Advanced Synthesis & Catalysis, 352, 2183-2188 (2010)
Oxidative amidation of activated alkenes using Pd(OAc)2 as a catalyst precursor
X. Liu and K. K. Hii,
European Journal of Organic Chemistry, 27, 5181-5189 (2010)
Yasunao Inoue et al.
Bioorganic & medicinal chemistry, 17(21), 7477-7486 (2009-10-09)
A series of peptide-based transition-state human neutrophil elastase (HNE) inhibitors with N-terminal acidic moieties were synthesized and their inhibitory activity against HNE was evaluated both in vitro and in vivo. Our results show that compounds containing cyclic amide bridged acidic
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