338605

Sigma-Aldrich

Methyl 3-hydroxy-5-isoxazolecarboxylate

98%

Empirical Formula (Hill Notation):
C5H5NO4
CAS Number:
Molecular Weight:
143.10
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

160-163 °C (lit.)

SMILES string

COC(=O)c1cc(O)no1

InChI

1S/C5H5NO4/c1-9-5(8)3-2-4(7)6-10-3/h2H,1H3,(H,6,7)

InChI key

BBFWUUBQSXVHHZ-UHFFFAOYSA-N

Application

Methyl 3-hydroxy-5-isoxazolecarboxylate was used in the enantioselective synthesis of a key precursor to the tetracycline antibiotics. It was also used in the preparation of formamidinopiperidine analog, an N-amidinopiperidine compound.

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

C B Xue et al.
Bioorganic & medicinal chemistry letters, 8(24), 3499-3504 (1999-02-06)
Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously...
Jason D Brubaker et al.
Organic letters, 9(18), 3523-3525 (2007-08-19)
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to...

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