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Merck
CN

862207

4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one

purified by recrystallization

Synonym(s):

2-Phenyl-1-4-heteromethylene-5-oxazolone, 2-Phenyl-4-(ethoxymethylene)-2-oxazolinone, 2-Phenyl-4-(ethoxymethylene)oxazolone, 2-Phenyl-4-ethoxymethylene-5-oxazolone, 4-(Ethoxymethylene)-2-phenyl-5(4H)-oxazolone, 4-Ethoxymethylene-2-phenyl oxazolone, 4-Ethoxymethylene-2-phenyl-5-oxazolone, Oxazolone

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About This Item

Empirical Formula (Hill Notation):
C12H11NO3
CAS Number:
15646-46-5
Molecular Weight:
217.22
NACRES:
NA.22
PubChem Substance ID:
24888573
UNSPSC Code:
12352100
EC Number:
239-713-9
MDL number:
MFCD00003204

Key Documents

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Product Name

4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one, purified by recrystallization

InChI

1S/C12H11NO3/c1-2-15-8-10-12(14)16-11(13-10)9-6-4-3-5-7-9/h3-8H,2H2,1H3/b10-8-

InChI key

SJHPCNCNNSSLPL-NTMALXAHSA-N

SMILES string

CCO\C=C1/N=C(OC1=O)c2ccccc2

form

solid

purified by

recrystallization

mp

94-96 °C (dec.) (lit.)

functional group

ester
ether
phenyl

storage temp.

2-8°C

Quality Level

100

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Application

4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one can be used as a reactant to synthesize:
  • Pyrimidinone derivatives with N-carboxymethylbenzamidine.
  • Multi-functionalized 1-azabicycles with acyclic enaminones via formal aza-[3+3] cycloaddition.
It can also be used as a source of alpha-amino acid residue to synthesize N-1,2,3-triazolyl substituted amino acid derivatives.

General description

4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one is a heterocyclic compound that belongs to the oxazolone family and serves as an important intermediate in the synthesis of amino acids, peptides, and heterocyclic precursors.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

pcodes

P280

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT7798
MKCS1471
MKCR1668
MKCJ8442
MKCF4919

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Yongyan Shi et al.
Cell death & disease, 11(6), 461-461 (2020-06-17)
Crohn's disease (CD) and ulcerative colitis (UC) actually had different pathological mechanisms, as the former was mainly induced by Th1 and Th17 response and the latter by Th2 response. Our previous study found that oxazolone-induced Th2-mediated colitis could not be
Joanne C Masterson et al.
Gut, 63(1), 43-53 (2012-11-20)
Eosinophilic oesophagitis (EoE) is a chronic inflammatory condition of the oesophagus with limited treatment options. No previous transgenic model has specifically targeted the oesophageal mucosa to induce oesophageal eosinophilia. We developed a mouse model that closely resembles EoE by utilising
Zenghui Lu et al.
The Journal of organic chemistry, 77(21), 9871-9877 (2012-10-11)
A novel palladium-catalyzed approach for the assembly of 3,4,5-trisubstituted oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reaction provides a convenient access
Nicolas Pradeille et al.
Chemistry & biodiversity, 9(11), 2528-2558 (2012-11-20)
The total syntheses of hypomurocin A3 and hypomuricin A5 (HM A3 and HM A5, resp.) in solution phase are described. These syntheses have been successfully achieved by applying the 'azirine/oxazolone method' to introduce the two Aib-Pro units into the backbone
Torsten Olszak et al.
Nature, 509(7501), 497-502 (2014-04-11)
The mechanisms by which mucosal homeostasis is maintained are of central importance to inflammatory bowel disease. Critical to these processes is the intestinal epithelial cell (IEC), which regulates immune responses at the interface between the commensal microbiota and the host.
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