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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
Amanda Waddell et al.
Inflammatory bowel diseases, 21(12), 2737-2746 (2015-08-28)
IL-33, a member of the IL-1 cytokine family that signals through ST2, is upregulated in ulcerative colitis (UC); however, the role of IL-33 in colitis remains unclear. IL-33 augments type 2 immune responses, which have been implicated in UC pathogenesis.
Boyi Liu et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(9), 3549-3563 (2013-06-01)
Allergic contact dermatitis is a common skin disease associated with inflammation and persistent pruritus. Transient receptor potential (TRP) ion channels in skin-innervating sensory neurons mediate acute inflammatory and pruritic responses following exogenous stimulation and may contribute to allergic responses. Genetic
Kenjyo Miyauchi et al.
Nature chemical biology, 9(2), 105-111 (2012-12-18)
N(6)-threonylcarbamoyladenosine (t(6)A) is a universally conserved, essential modified nucleoside found in transfer RNAs (tRNAs) responsible for ANN codons in all three domains of life. t(6)A has a crucial role in maintaining decoding accuracy during protein synthesis. The presence of t(6)A
Sylvère Durand et al.
The journal of physical chemistry. A, 117(12), 2508-2516 (2013-02-27)
The structure of peptide fragments was studied using "action" IR spectroscopy. We report on room temperature IR spectra of b4 fragments of protonated GGGGG, AAAAA, and YGGFL in the X-H (X = C, N, O) stretching region. Experiments were performed
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