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230138

Sigma-Aldrich

Oxazole

98%

Synonym(s):

1,3-Oxazole, 3-Azafuran

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About This Item

Empirical Formula (Hill Notation):
C3H3NO
CAS Number:
Molecular Weight:
69.06
Beilstein:
103851
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

Assay

98%

refractive index

n20/D 1.425 (lit.)

bp

69-70 °C (lit.)

mp

−87-−84 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

SMILES string

c1cocn1

InChI

1S/C3H3NO/c1-2-5-3-4-1/h1-3H

InChI key

ZCQWOFVYLHDMMC-UHFFFAOYSA-N

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General description

Oxazole is the parent molecule for a large class of heterocyclic aromatic compounds. It is a weak base that can be used as an electron-deficient diene in the Diels-Alder cycloaddition reaction[1][2]. It undergoes nitration, sulfonation, halogenation, Friedel-Crafts alkylation, and acylation.

Application

Oxazole can be used:
  • in the intramolecular Diels–Alder (IMDA) cycloaddition reaction to synthesis natural products
  • as a precursor in the ring opening, nucleophilic addition and recyclization as well as [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

66.2 °F - closed cup

Flash Point(C)

19 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Dawid Siodłak et al.
The journal of physical chemistry. B, 118(9), 2340-2350 (2014-02-18)
Oxazole ring occurs in numerous natural peptides, but conformational properties of the amino acid residue containing the oxazole ring in place of the C-terminal amide bond are poorly recognized. A series of model compounds constituted by the oxazole-amino acids occurring
Oxazole as an Electron-Deficient Diene in the Diels-Alder Reaction
Suarez-Moreno G, et al.
Organic Letters, 13, 6358-6361 (2011)
Kristjan Bloudoff et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(1), 95-100 (2016-12-21)
Nonribosomal peptide synthetases (NRPSs) are a family of multidomain, multimodule enzymes that synthesize structurally and functionally diverse peptides, many of which are of great therapeutic or commercial value. The central chemical step of peptide synthesis is amide bond formation, which
Santosh Kumar et al.
Science advances, 6(42) (2020-10-18)
Diatoms are an abundant group of microalgae, known for their ability to form an intricate cell wall made of silica. Silicon levels in seawater are in the micromolar range, making it a challenge for diatoms to supply the rapid intracellular
Systematic scientific study of 1, 3-oxazole derivatives as a useful lead for pharmaceuticals: A review
Joshi S, et al.
The pharma innovation journal, 6, 109-109 (2017)

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