1008-75-9

Basic information

• Product Name: 3-METHYL-5-PHENYLISOXAZOLE
• Synonyms: Isoxazole, 3-methyl-5-phenyl- (6CI,7CI,8CI,9CI);3-Methyl-5-phenylisoxazole ,97%;5-Phenyl-3-methylisoxazole;3-methyl-5-phenyl-1,2-oxazole;3-methyl-5-phenyloxazole
• CAS NO: 1008-75-9
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.19
• Product Categories: OXAZOLE;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1008-75-9.mol

Chemical Properties

• Melting Point: 63-68 °C
• Boiling Point: 262-264 °C/760 mmHg
• Flash Point: 112.7°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 0.00668mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.38±0.28(Predicted)
• CAS DataBase Reference: 3-METHYL-5-PHENYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-5-PHENYLISOXAZOLE(1008-75-9)
• EPA Substance Registry System: 3-METHYL-5-PHENYLISOXAZOLE(1008-75-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 1008-75-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-5-PHENYLISOXAZOLE is used as an Aminopeptidase A inhibitor for its potential therapeutic applications. Aminopeptidase A is an enzyme that plays a role in various biological processes, and its inhibition can be beneficial in treating certain conditions. By targeting this enzyme, 3-METHYL-5-PHENYLISOXAZOLE may contribute to the development of new drugs or therapies in the pharmaceutical industry.
Additionally, due to its white crystalline structure and chemical properties, 3-METHYL-5-PHENYLISOXAZOLE may have other potential applications in different industries, such as in the synthesis of other compounds or as an intermediate in chemical reactions. However, more information would be needed to determine its specific uses in these areas.

InChI:InChI=1/C10H9NO/c1-8-7-10(12-11-8)9-5-3-2-4-6-9/h2-7H,1H3

Upstream product

• 1817-57-8 4-phenyl-3-butyne-2-one 
• 24334-85-8 3-Methyl-5-phenyl-isoxazol 
• 77242-15-0 tert-butyldimethylsilyl nitronate ester 
• 4440-01-1 lithium phenylacetylide 
• 7803-49-8 hydroxylamine 
• 93-91-4 1-phenylbutan-1,3-dione 
• 64-17-5 ethanol 
• 55337-45-6 4-ethoxy-4-phenyl-but-3-en-2-one 
• 34880-85-8 3-chloro-1-phenylbutan-1-one 
• 40806-69-7 3,4-dichloro-4-phenyl-butan-2-one 
• 7647-01-0 hydrogenchloride 
• 53120-17-5 1-phenyl-1,3-pentanedionedioxime 
• 7664-93-9 sulfuric acid 
• 78664-25-2 N-(1-Hydroxyimino-1-phenyl-3-butyl)hydroxylamine 

Downstream Products

• 52063-44-2 3-methyl-5-(4-nitrophenyl)isoxazole 
• 23652-90-6 3-amino-1-phenylbut-2-en-1-one 
• 56426-41-6 3-methyl-5-phenylpyrazole 
• 52266-11-2 2,3-dimethyl-5-phenyl-4-isoxazoline 
• 14091-93-1 3-(methylamino)-1-phenylbut-2-en-1-one 
• 127916-08-9 1-(3-methyl-5-phenylisoxazol-4-yl)ethanone 
• 142231-26-3 5-phenyl-3-(2-oxopropyl)isoxazole 
• 123371-88-0 4-(1-hydroxypropyl)-3-methyl-5-phenylisoxazole 
• 875475-50-6 3-(trimethylsilylmethyl)-5-phenylisoxazole 
• 93-91-4 1-phenylbutan-1,3-dione 

Relevant articles and documents

Efficient and convenient method for the synthesis of isoxazoles in ionic liquid

An efficient one-pot synthesis of 3,5-disubstitueted isoxazoles from β-diketones in room temperature ionic liquids (ILs) is described. Compared with the classical reaction conditions, this new synthetic method is environmentally friendly and has the advan

Convenient synthesis of 3,5-disubstituted isoxazoles

α,β-Unsaturated oximes obtained from the corresponding α,β-unsaturated ketones on treatment with 2 equivalents of manganese dioxide in refluxing chloroform gives 3,5-disubstituted isoxazoles in good yields. Copyright Taylor & Francis Group, LLC.

SYNTHESIS AND REACTIONS OF 5-(TRIBUTYLSTANNYL)ISOXAZOLES

3-Substituted 5-(tributylstannyl)isoxazoles were synthesized in good yields by the 1,3-dipolar cycloaddition reaction of ethynyltributylstannane with nitrile oxides generated in situ. 3-Methyl-5-(tributylstannyl)isoxazole was easily converted to the corre

An improved method for preparation of nitrile oxides from nitroalkanes for in situ dipolar cycloadditions

A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethylaminopyridine (3) as catalyst in the presence of dipolarophiles

Reactivity of p-phenyl substituted β-enamino compounds using k- 10/ultrasound. II [1]. Synthesis of isoxazoles and 5-isoxazolones

The condensation of 4-phenyl substituted β-enamino ketones 1a-d and β- enamino esters 5a-d with hydroxylamine hydrochloride using K-10 as the solid support under sonication was studied to evaluate the formation of isoxazole and 5-isoxazolone rings from β-enamino compounds with a substituted aromatic ring. Isoxazoles 2a-c, 3c-d and 5-isoxazolones 6a-c and 7a-d were obtained. The use of K-10/ultrasound in this reaction furnished novel results in some cases.

A photochemical one-pot three-component synthesis of tetrasubstituted imidazoles

Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, α-aminonitriles, and isoxazoles. Condensation of the first two components produces α-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C2-C3 bond of the acylazirine. The reaction mechanism was studied by DFT calculations. (Chemical Equation Presented)

Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles

Isoxazoles, mainly 3,5-disubstituted, are prepared by catalytic condensation of primary nitro compounds with terminal acetylenes by using a copper/base catalytic system. The additional catalytic effect of the copper(II) salts is evidenced by comparing the kinetic profiles. Selectivity dependence on reaction conditions is considered for phenylacetylene in the following competitive processes: oxidative coupling of terminal alkynes to conjugated diynes catalyzed by CuIIand base in the presence of air; production of furazans beside condensation with benzoylnitromethane to 3-benzoylisoxazoles, as a result of the reaction of the dipolarophile with 3,4-dibenzoylfuroxan; addition of electron-poor alkynes (e.g., methyl propiolate) with themselves and with the nitro compound. Thus, oxidative coupling is negligible in reactions with “active” nitro compounds, whereas with nitroalkanes both products are observed: only trace amounts of isoxazoles are detected without copper. Similarly, in the presence of copper, 3-benzoyl-5-phenylisoxazole is predominant over the furazan. Furthermore, condensations of electron-poor alkynes give complex reaction mixtures in the presence of base alone, but cycloadducts are conveniently prepared with copper. The results indicate the practical and general utility of this catalytic method for synthetic practice.

NH2OH-HCl-Mediated Umpolung α-Methylsulfonylation of α-Sulfonyl Ketones with Methylsulfoxides: Synthesis of α,β-Bis-sulfonyl Arylketones

In this paper, a novel and efficient route for the synthesis of α,β-bis-sulfonyl arylketones via an NH2OH-HCl-mediated intermolecular umpolung α-methylsulfonylation of α-sulfonyl ketones with methylsulfoxides is described. A plausible mechanism is proposed and discussed. Various reaction conditions for this efficient, one-pot, environmentally friendly transformation were investigated.

NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?

The first NHC-palladium-catalyzed regioselective oxyarylation of oxime ether in a task-specific ionic liquid via C(sp3)-O and C(sp2)-O bond cleavage of two different types of ethers for the assembly of structurally diverse 4-arylisoxazoles is described. Both the basic ionic liquid [C3NH2mim]Br and NHC-Pd catalyst IPr-Pd-Im-Cl2 played an important role in this transformation. Notably, this new approach provides a practical and straightforward route to access a broad range of privileged 4-arylisoxazole structures with good yields and excellent regioselectivities. Significantly, this catalytic system can be recycled up to eight times without significant loss of catalytic activity.

AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.