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I601

Sigma-Aldrich

2-Imidazolidone

96%

Synonym(s):

2-Oxoimidazolidine, N,N′-Ethyleneurea

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O
CAS Number:
120-93-4
Molecular Weight:
86.09
Beilstein:
106252
EC Number:
204-436-4
MDL number:
MFCD00005257
UNSPSC Code:
12352100
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

Health hazardExclamation mark
GHS08,GHS07

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

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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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)
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)
Synthesis and antimicrobial activity of new heterocycles obtained using cyanoacetylation
Sh. M. Abu-Bakr, et al.,
Pharmaceutical Chemistry Journal, 44, 433-437 (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
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
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