118994-86-8

Basic information

• Product Name: 5-OXAZOLECARBOXALDEHYDE
• Synonyms: 5-OXAZOLECARBOXALDEHYDE;OXAZOLE-5-CARBALDEHYDE;5-Oxazolecarboxaldehyde (9CI);1,3-oxazole-5-carbaldehyde;tert-butyl 1-aMino-8-azaspiro[4.5]decane-8-carboxylate;oxazole-5-carboxaldehyde;5-Formyloxazole;1,3-Oxazole-5-carboxaldehyde
• CAS NO: 118994-86-8
• Molecular Formula: C₄H₃NO₂
• Molecular Weight: 97.07
• Product Categories: ALDEHYDE
• Mol File: 118994-86-8.mol

Chemical Properties

• Melting Point: 30-32℃
• Boiling Point: 184.7 °C at 760 mmHg
• Flash Point: 65.504 °C
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 0.723mmHg at 25°C
• Refractive Index: 1.519
• PKA: -1.09±0.10(Predicted)
• CAS DataBase Reference: 5-OXAZOLECARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-OXAZOLECARBOXALDEHYDE(118994-86-8)
• EPA Substance Registry System: 5-OXAZOLECARBOXALDEHYDE(118994-86-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• Hazardous Substances Data: 118994-86-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Oxazolecarboxaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex organic molecules that can exhibit therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Oxazolecarboxaldehyde serves as a building block for the preparation of compounds that can be used in the development of pesticides and other agricultural chemicals, contributing to crop protection and enhancement.
Used in Organic Synthesis:
5-Oxazolecarboxaldehyde is utilized as a versatile intermediate in organic synthesis for its capacity to engage in multiple chemical reactions, facilitating the creation of a wide array of complex organic molecules with potential applications in various fields.
Used in the Synthesis of Heterocycles:
5-Oxazolecarboxaldehyde is employed as a reactant in the synthesis of nitrogen-containing heterocycles such as pyrazoles and benzothiazoles, which are important in various chemical and pharmaceutical applications due to their unique properties and structures.

InChI:InChI=1/C4H3NO2/c6-2-4-1-5-3-7-4/h1-3H

Upstream product

• 104336-01-8 5-((diethoxy)methyl)oxazole 
• 127232-41-1 1,3-oxazol-5-ylmethanol 
• 75-09-2 dichloromethane 
• 7732-18-5 water 
• 118994-89-1 oxazol-5-yl-carboxylic acid ethyl ester 

Downstream Products

• 127232-41-1 1,3-oxazol-5-ylmethanol 
• 214550-89-7 [4-(tert-Butyl-diphenyl-silanyloxymethyl)-oxazol-2-yl]-oxazol-5-yl-methanol 
• 321434-76-8 (4R)-N-[(2-chloro-6-methylphenyl)methyl]-3-[(2S,4S)-5-[((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)amino]-2-hydroxy-4-(5-oxazolylmethyl)-1,5-dioxopentyl]-5,5-dimethyl-4-thiazolidinecarboxamide 
• 1029800-20-1 (2RS,4R)-2-(2-fluorophenyl)-thiazolidine-4-carboxylic acid 
• 911491-47-9 C₂₁H₂₂FN₅O₄ 
• 1453853-38-7 (4-chloro-3-fluorophenyl)(oxazol-5-yl)methanol 

Relevant articles and documents

Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand

Oxazole-type fluorophores show an increase of fluorescence intensity upon interaction with nucleic acids, and therefore can be used as tools for nucleic acid-sensing and fluorescence imaging. Here, we developed a novel stilbene-type fluorophore, MO-VN (1), consisting of a mono oxazole bearing a vinyl naphthalene moiety. This compound (1) was embedded in a trioxazole2and a cyclic hexaoxazole3a. The fluorescence properties of1,2, and3awere evaluated in the presence of various nucleic acid sequences. Compound3showed significant fluorescent enhancement upon interacting with G-quadruplex (G4) structure, which plays critical roles in various biological phenomena. Further structural development focusing on the vinyl naphthalene moiety of3aafforded a turn-on type G4 ligand3ethat shows G4-specific fluorescence. Measurement of the fluorescence of3eduring titration of a telomeric DNA, telo24, with its C-rich complementary sequence, which unwinds the G4 structure, allowed us to monitor the dynamics of G4.

SUBSTITUTED THIAZOLE OR OXAZOLE P2X7 RECEPTOR ANTAGONISTS

The present invention refers to novel substituted thiazole and oxazole compounds of formula (I) having P2X7 receptor (P2X7) antagonistic properties. The compounds are useful in the treatment or prophylaxis of diseases associated with P2X7 receptor activity in animals, in particular humans.

Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4-and 5-(o-vinylstyryl) oxazoles

Novel cis/trans-4- and cis/trans -5-(2-vinylstyryl)oxazoles have been synthesized by Wittig reactions from the diphosphonium salt of α,α'- o -xylene dibromide, formaldehyde and 4- and 5-oxazolecarbaldehydes, respectively. In contrast, trans -5-(2-vinylsty

Application of flow chemistry to the selective reduction of esters to aldehydes

The reduction of esters to aldehydes is an important transformation in organic chemistry and several reducing agents have been described. However, the use of this reaction in medicinal and natural product chemistry is limited due to the instability of the intermediates and the high reactivity of the reaction products. In the current article, the general and selective reduction of esters with diisobutyl-tert-butoxyaluminum hydride in flow is reported. This reagent allows esters to be reduced in the presence of different functional groups, including those considered to be of similar or higher reactivity. Copyright

Total synthesis of the potent antifungal agents bengazole C and E

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

TAXANE COMPOUND WITH AZETIDINE RING STRUCTURE

A compound represented by the general formula (1) [X1 and X2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R1 represents a phenyl group, R2 represents an alkyl group, an alkenyl group, or

Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B

The bengazoles are a family of marine natural products that display potent antifungal activity and a unique structure, containing two oxazole rings flanking a single carbon atom. Total syntheses of bengazole A and B are described, which contain a sensitive stereogenic centre at this position between the two oxazolcs. Additionally, the synthesis of 10-epi-bengazole A is reported. Two parallel synthetic routes were investigated, relying on construction of the 2,4-disubstituted oxazole under mild conditions and a diastereoselective 1,3-dipolar cycloaddition. Our successful route is high yielding, provides rapid access to single stereoisomers of the complex natural products and allows the synthesis of analogues for biological evaluation.

Discovery of ritonavir, a potent inhibitor of HIV protease with high oral bioavailability and clinical efficacy

The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption. Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 μM) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

Synthetic studies on bengazoles of marine sponge origin. Synthesis of the core bis-oxazole fragments

The core bis-oxazole fragment 3 was constructed by the coupling of the aldehyde (6) with the lithiated oxazoles (7), oxidation of the resulting bis-oxazolyl methanol (11), followed by the asymmetric reduction with (R)-(+)-BINAL-H as key steps. Preparation of another bis-oxazole fragment (4) was accomplished by the Barton-McCombie radical deoxygenation reaction of 11.