288-14-2

Basic information

• Product Name: Isoxazole
• Synonyms: ISOXAZOLE;1-Oxa-2-azacyclopentadiene;Isooxazole;ISOXAZOLE 98+%;1,2-Oxazole;Isoxazole,99%;Different oxazole;Isoxazole 99%
• CAS NO: 288-14-2
• Molecular Formula: C₃H₃NO
• Molecular Weight: 69.06
• EINECS: 206-018-7
• Product Categories: Isoxazoles, Oxadiazoles, Oxazoles;pharmacetical;Boronic ester;Isoxazole;Organoborons;Thiophens;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 288-14-2.mol
• Article Data: 41

Chemical Properties

• Melting Point: -67.1°C
• Boiling Point: 93-95 °C(lit.)
• Flash Point: 48 °F
• Appearance: colorless liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Density: 2.4 (vs air)
• Vapor Pressure: 51.7mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: Store at RT.
• Solubility: 167g/l
• PKA: -2.0(at 25℃)
• BRN: 103773
• CAS DataBase Reference: Isoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole(288-14-2)
• EPA Substance Registry System: Isoxazole(288-14-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11
• Safety Statements: 16-23/33-33-29-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 288-14-2(Hazardous Substances Data)

Usage

Description

As an important class of heterocycles, isoxazole is a five membered heterocyclic compound with various pharmacological actions, which is found in some natural products, such as ibotenic acid. It is used in the formation of the basis for a number of drugs, such as the COX-2 inhibitor valdecoxib and anti-inflammatory drugs. Isoxazoles are largely applied in the area of pharmaceuticals and therapeutics, including insecticidal, antibacterial, antibiotic, antitumour, antifungal, antituberculosis, anticancer and ulcerogenic. Besides, it has a great effect on reducing blood glucose, eliminating pain, resisting inflammation, killing harmful bacteria, controlling and reducing the risk of HIV. The isoxazole ring is an essential pharmacophore in modern drug discovery. Some beta-lactamase-resistant antibiotics contain an isoxazole group, including cloxacillin, dicloxacillin, flucloxacillin, and the isoxazole group is also found in some steroid drug such as danazol.

References

https://en.wikipedia.org/wiki/Isoxazole http://www.ijpcbs.com/files/volume3-2-2013/15.pdf

Chemical Properties

Colorless liquid

Uses

Natural insecticide.

Definition

ChEBI: A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.

General Description

Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter.

Hazard

Narcotic and psychomimetic effects.

InChI:InChI=1/C3H3NO/c1-2-4-5-3-1/h1-3H

Synthetic route

di(1,3-dioxolan-2-yl)methane (4405-17-8) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydroxylamine hydrochloride at 110 - 120℃; Green chemistry;	85.5%

malondialdehyde bis(diethyl acetal) (122-31-6) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydroxylamine hydrochloride In water at 70℃; for 3.5h;	43%
With hydrogenchloride; water; hydroxylamine
With hydrogenchloride; hydroxylamine
With hydroxylamine hydrochloride

Trimethylsilanecarbonitrile oxide (84405-51-6) + acetylene (74-86-2) → ISOXAZOLE (288-14-2)

Conditions	Yield
In tetrahydrofuran; water under 760 Torr; for 1.5h; Ambient temperature;	28%
With water In tetrahydrofuran Ambient temperature; Yield given;

Propargylic aldehyde (624-67-9) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydroxylamine
With hydrogenchloride; hydroxylamine

1,3,3-triethoxypropene (5444-80-4) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydrogenchloride; water; hydroxylamine

vinyl acetate (108-05-4) + sodium cyanate (15736-98-8) → ISOXAZOLE (288-14-2)

Conditions	Yield
With sulfuric acid Erhitzen des Reaktionsprodukts mit wss. H2SO4;

3t-chloro-propenal (4643-13-4) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydrogenchloride; water; hydroxylamine

acetic acid-(1-bromo-3,3-dichloro-propyl ester) (98021-69-3) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydrogenchloride; ethanol; hydroxylamine
With hydrogenchloride; ethanol; hydroxylamine; sodium acetate

1-acetoxy-1,3,3-tribromopropane (86046-91-5) → ISOXAZOLE (288-14-2)

Conditions	Yield
With hydrogenchloride; ethanol; hydroxylamine
With hydrogenchloride; ethanol; hydroxylamine; sodium acetate

sodium cyanate (15736-98-8) + acetylene (74-86-2) → ISOXAZOLE (288-14-2) + isoxazole-3-carbaldehyde-oxime

Conditions	Yield
With sulfuric acid

Propargylic aldehyde (624-67-9) + hydroxylamine (7803-49-8) → ISOXAZOLE (288-14-2)

ISOXAZOLE (288-14-2) → 3-aminoprop-2-enal (25186-34-9)

Conditions	Yield
With hydrogen; nickel In methanol at 20℃; under 2068.65 Torr;	100%
With hydrogen; Raney nickel In methanol under 2068.65 Torr; for 24h; Parr apparatus;	94%
With hydrogen; nickel In methanol; chloroform

ISOXAZOLE (288-14-2) + Oxone + 3-methyl-4-(4-methylthiophenyl)-5-phenylisoxazole (219679-74-0) → 3-methyl-5-(4-methylsulfonylphenyl)-4-phenylisoxazole (181695-93-2)

Conditions	Yield
In tetrahydrofuran; methanol; water	95%

ISOXAZOLE (288-14-2) + 1,5-diphenylpenta-1,4-diyn-3-ol (15814-32-1) → (Z)-1-(3-oxoprop-1-en-1-yl)-2,5-diphenyl-1H-pyrrole-3-carbaldehyde

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere; chemoselective reaction;	94%

ISOXAZOLE (288-14-2) + 1,5-di(thiophen-3-yl)penta-1,4-diyn-3-ol (1613231-71-2) → (Z)-1-(3-oxoprop-1-en-1-yl)-2,5-di(thiophen-3-yl)-1H-pyrrole-3-carbaldehyde

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 5h; Inert atmosphere; chemoselective reaction;	93%

ISOXAZOLE (288-14-2) + carbon dioxide (124-38-9) → isoxazole-5-carboxylic acid (21169-71-1)

Conditions	Yield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h; Stage #2: ISOXAZOLE In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;	91%

ISOXAZOLE (288-14-2) + 1-(4-bromophenyl)-5-cyclopropylpenta-1,4-diyn-3-ol → (Z)-5-(4-bromophenyl)-2-cyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 3h; Inert atmosphere; chemoselective reaction;	91%

ISOXAZOLE (288-14-2) + (3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene → C15H11NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 14h; Reagent/catalyst;	88%

ISOXAZOLE (288-14-2) + C11H12O → (Z)-2,5-dicyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 7h; Inert atmosphere; chemoselective reaction;	87%

ISOXAZOLE (288-14-2) + 4-methoxydeca-1,2-dien-5-yne → C13H15NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 20h;	87%

ISOXAZOLE (288-14-2) + 2-(2-phenylethenyl)-5-methoxybenzaldehyde (223553-44-4) → C19H13NO2 + C19H15NO3

Conditions	Yield
With copper diacetate In toluene at 110℃; for 5h; regioselective reaction;	A 87% B 7%

ISOXAZOLE (288-14-2) + C12(13)CH12O → C14(13)CH11NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 25h;	85%

ISOXAZOLE (288-14-2) + 1-(3-methoxyhexa-4,5-dien-1-yn-1-yl)-4-methylbenzene → C16H13NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 23h;	85%

ISOXAZOLE (288-14-2) + o-(phenylethynyl)benzaldehyde (59046-72-9) → 4-benzoyl-2-naphthonitrile + C18H13NO2

Conditions	Yield
With copper diacetate In toluene at 110℃; for 4h; regioselective reaction;	A 85% B 8%

ISOXAZOLE (288-14-2) + 2-[(4-chlorophenyl)ethynyl]benzaldehyde (1251832-81-1) → C18H10ClNO + C18H12ClNO2

Conditions	Yield
With copper diacetate In toluene at 110℃; for 3.5h; regioselective reaction;	A 85% B 8%

ISOXAZOLE (288-14-2) + 4-(3-(4-methylpiperazinyl)-1-propoxy)-5-methoxy-2-aminobenzoic acid methyl ester → 7-(3-(4-methylpiperazinyl)-1-propoxy)-4-one-6-methoxyquinoline-3-carbonitrile

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 5h;	85%

ISOXAZOLE (288-14-2) + N,4-dimethyl-N-(3-methylbut-3-en-1-yn-1-yl)benzenesulfonamide → C16H18N2O3S + C17H20N2O3S

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2-(3H)-ylidene]gold(I)chloride; silver(I) triflimide In 1,2-dichloro-ethane at 70℃; for 4h;	A 84% B 8%

ISOXAZOLE (288-14-2) + C17H14O → C19H13NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 24h;	84%

ISOXAZOLE (288-14-2) + C13H10(2)H2O → C15H9(2)H2NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 12h;	83%

ISOXAZOLE (288-14-2) + 1-chloro-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene → C15H10ClNO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 24h;	83%

ISOXAZOLE (288-14-2) + (Z)-p-chlorobenzaldehyde oxime (3717-23-5) + toluene-4-sulfonamide (70-55-3) + phenylacetylene (536-74-3) → 3-(4-chlorophenyl)-4-phenylisoxazole (130966-62-0)

Conditions	Yield
With chloroamine-T In methanol; water	82%

ISOXAZOLE (288-14-2) + (S)-tert-butyl 2-((5-ethynylpyridin-3-yloxy)methyl)azetidine-1-carboxylate (1222139-46-9) + 2-(2-nitroethoxy)tetrahydro-2H-pyran (75233-61-3) → 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-isoxazolyl]pyridine (1222139-58-3)

Conditions	Yield
With phenyl isocyanate; triethylamine In hexane; benzene at 60℃; for 24h;	82%

ISOXAZOLE (288-14-2) + 1-(tert-butyl)-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene → C19H19NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 23h;	82%

ISOXAZOLE (288-14-2) + carbon dioxide (124-38-9) + methyl iodide (74-88-4) → methyl 1,2-oxazole-5-carboxylate (15055-81-9)

Conditions	Yield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h; Stage #2: ISOXAZOLE In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h; Stage #3: methyl iodide In tetrahydrofuran regioselective reaction;	81%

ISOXAZOLE (288-14-2) + C12H18O → C14H17NO

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 33h;	81%

ISOXAZOLE (288-14-2) + titanium tetrachloride (7550-45-0) → TiCl4(C3H3NO)2 (161645-55-2)

Conditions	Yield
In benzene (N2); stirring; filtn., washing (benzene), drying (vac.); elem. anal.;	80%

Upstream product

• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 98021-69-3 acetic acid-(1-bromo-3,3-dichloro-propyl ester) 
• 86046-91-5 1-acetoxy-1,3,3-tribromopropane 
• 15736-98-8 sodium cyanate 
• 74-86-2 acetylene 
• 32830-84-5 5-methyl-3-oxo-hex-4-enal 
• 7803-49-8 hydroxylamine 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 54494-88-1 3,8-dimethyl-nonane-2,4-dione 
• 5444-80-4 1,3,3-triethoxypropene 
• 7732-18-5 water 
• 624-67-9 Propargylic aldehyde 
• 84405-51-6 Trimethylsilanecarbonitrile oxide 
• 4643-13-4 3t-chloro-propenal 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 201230-82-2 carbon monoxide 
• 107-13-1 acrylonitrile 
• 75-05-8 acetonitrile 
• 107-12-0 propiononitrile 
• 74-86-2 acetylene 
• 847490-69-1 4-iodoisoxazole 
• 130966-62-0 3-(4-chlorophenyl)-4-phenylisoxazole 
• 216388-88-4 C₃H₃Cl₃NOPt^(1-)*C₂₅H₂₂P⁽¹⁺⁾, II 
• 326818-05-7 4-[5-Benzyloxymethyl-3-(4-fluoro-phenyl)-isoxazol-4-yl]-2-methylsulfanyl-pyrimidine 
• 6162-76-1 cyanoacetaldehyde 
• 3463-30-7 1-(4-nitrophenyl)pyrazole 
• 214540-65-5 (E)-2-Formyl-3-[2-(3-methyl-but-2-enyloxy)-phenyl]-acrylonitrile 
• 73028-29-2 3-chloro-isoxazole 

Relevant articles and documents

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Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes 9a-9c were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole derived oxetanes show type T photochromism.

NOVEL FLORFENICOL-TYPE ANTIBIOTICS

The present invention relates to novel florfenicol compounds having the chemical structure: wherein the compounds are useful for the treatment and/or prevention of bacterial infections in a broad range of patients such as, without limitation, birds, fish, shellfish and mammals