1006-67-3

Basic information

• Product Name: 5-PHENYLISOXAZOLE
• Synonyms: BUTTPARK 81\09-55;5-PHENYLISOXAZOLE;1-(Isoxazol-5-yl)benzene;5-Phenyl-1,2-oxazole;Isoxazole, 5-phenyl-
• CAS NO: 1006-67-3
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• Mol File: 1006-67-3.mol

Chemical Properties

• Melting Point: 22°C(lit.)
• Boiling Point: 260°C(lit.)
• Flash Point: 127.4 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 0.00675mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• PKA: -3.02±0.50(Predicted)
• CAS DataBase Reference: 5-PHENYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYLISOXAZOLE(1006-67-3)
• EPA Substance Registry System: 5-PHENYLISOXAZOLE(1006-67-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 1006-67-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 3593, 1967 DOI: 10.1021/jo01286a065

InChI:InChI=1/C9H7NO/c1-2-4-8(5-3-1)9-6-7-10-11-9/h1-7H

Upstream product

• 123-91-1 1,4-dioxane 
• 75-52-5 nitromethane 
• 4440-01-1 lithium phenylacetylide 
• 536-74-3 phenylacetylene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 7145-48-4 Benzoylacetaldehyde ω-oxime 
• 53009-60-2 3-(hydroxyimino-(seqcis))-1-phenyl-propan-1-one 
• 108-24-7 acetic anhydride 
• 3623-15-2 phenyl propargyl ketone 
• 10557-74-1 3-bromo-5-phenylisoxazole 
• 55337-55-8 2-(2-oxo-2-phenyl-ethyl)-1,3-dioxolane 
• 13372-81-1 cinnamaldoxime 
• 84405-51-6 Trimethylsilanecarbonitrile oxide 
• 75-05-8 acetonitrile 

Downstream Products

• 103030-37-1 4-chloromethyl-5-phenyl-isoxazole 
• 614-16-4 Benzoylacetonitrile 
• 114514-93-1 N-Methyl-5-phenyl-isoxazolium-methosulfat 
• 3445-76-9 5-phenyl-3H-1,2-dithiole-3-thione 
• 10557-73-0 4-bromo-5-phenyl-isoxazole 
• 99066-75-8 4-nitro-5-phenyl-isoxazole 
• 3383-42-4 5-(4-nitrophenyl)isoxazole 
• 84637-25-2 3-(4-nitro-phenylhydrazono)-3-phenyl-propionitrile 
• 174652-94-9 1-phenyl-2-cyano-3-dimethylaminopropen-1-one 
• 38518-76-2 2-amino-4H-1-benzopyran-4-one 
• 126633-02-1 5-(3-nitrophenyl)isoxazole 
• 31301-43-6 4-Chloro-5-phenylisoxazole 
• 5765-41-3 4-isoxazol-5-ylbenzenesulfonyl chloride 
• 3383-40-2 4-nitro-5-(4-nitro-phenyl)-isoxazole 

Relevant articles and documents

Harnessing Stereospecific Z-Enamides through Silver-Free Cp?Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles

The stereospecific synthesis of Z-enamides is described in this paper. For the first time, isoxazoles have been employed as electrophiles in C-H functionalization to afford thermodynamically less stable Z-enamides utilizing salicylaldehydes in an atom- and step-economic fashion. The stereochemistry of enamides might originate from the relative disposition of atoms present in isoxazole and the intramolecular hydrogen bonding. The reaction showed excellent scope as several structurally and electronically diverse salicylaldehydes and isoxazoles reacted efficiently.

Photochemistry of 4- and 5- phenyl substituted isoxazoles

5-Phenylisoxazole (4) and 4-phenylisoxazole (22) underwent phototransposition to 5-phenyloxazole (5) and 4-phenyloxazole (24) respectively. Labeling with deuterium or methyl confirmed that these phototrans-positions occurred via the P4 pathway which involves only interchange of the N2 and C3 ring position. Thus, 4-deuterio-5-phenylisoxazole (4-4d), 4-methyl-5-phenylisoxazole (10), and 5-methyl-4-phenylisoxazole (23) phototransposed to 4-deuterio-5-phenyloxazole (5-4d), 4-methyl-5-phenyloxazole (11), and 5-methyl-4-phenyloxazole (25) respectively. In addition to phototransposition, isoxazoles 4, 10, and 23 also underwent photo-ring cleavage to yield benzoylacetonitrile (9), α-benzoylpropionitrile (15), and aceto-α-phenyl-acetonitrile (26) respectively. Irradiation of 5-phenyl-3-(trifluoromethyl)isoxazole (16) in acetonitrile led to 5-phenyl-2-(trifluoromethyl)oxazole (17), the P4 phototransposition product. Irradiation of 16 in methanol led to a substantial decrease in the yield of 17 and to the formation of a mixture of (E) and (Z)-2-methoxy-2- (trifluoromethyl)-3-benzoylaziridines 18a and 18b.

A convenient procedure for transformation of tertiary cyclopropanols into 5-substituted isoxazoles

Tertiary cyclopropanols, when treated with an excess of amyl nitrite at room temperature, are smoothly converted into dimeric β-nitrosoketones. Heating the methanolic solutions of the latter under reflux gives 5-substituted isoxazoles in good yields. Geor

Cracking under internal pressure: Photodynamic behavior of vinyl azide crystals through N2release

When exposed to UV light, single crystals of the vinyl azides 3- azido-1-phenylpropenone (1a), 3-azido-1-(4-methoxyphenyl)propenone (1b), and 3-azido-1-(4-chlorophenyl)propenone (1c) exhibit dramatic mechanical effects by cracking or bending with the release of N2. Mechanistic studies using laser flash photolysis, supported by quantum mechanical calculations, show that each of the vinyl azides degrades through a vinylnitrene intermediate. However, despite having very similar crystal packing motifs, the three compounds exhibit distinct photomechanical responses in bulk crystals. While the crystals of 1a delaminate and release gaseous N2 indiscriminately under paraffin oil, the crystals of 1b and 1c visibly expand, bend, and fracture, mainly along specific crystallographic faces, before releasing N2. The photochemical analysis suggests that the observed expansion is due to internal pressure exerted by the gaseous product in the crystal lattices of these materials. Lattice energy calculations, supported by nanoindentation experiments, show significant differences in the respective lattice energies. The calculations identify critical features in the crystal structures of 1b and 1c where elastic energy accumulates during gas release, which correspond to the direction of the observed cracks. This study highlights the hitherto untapped potential of photochemical gas release to elicit a photomechanical response and motility of photoreactive molecular crystals.

Preparation method of isoxazole derivative

The invention relates to a preparation method of an isoxazole derivative, which comprises the following steps of mixing an propargyl alcohol derivative, a halogen source, an acid and a solvent, and heating to react; adding the hydroxylamine into the react

Copper Photoredox Catalyzed A3’ Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process

The first successful example of the three-component coupling of N-alkylanilines, terminal alkynes, and alcohols was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox hydrogen-atom transfer process. This method allows pre

A novel synthesis of 5-substituted isoxazoles from propargylic amines and N-hydroxyphthalimide

A mild and efficient method for the synthesis of 5-substituted isoxazoles through cyclization of propargylic amines with N-hydroxyphthalimide (NHPI) under metal-free conditions was developed.

Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN3

A novel and efficient TEMPO-catalyzed synthesis of 5-substituted isoxazoles from propargylic ketones and TMSN3via a radical mechanism process is described. This methodology provides an easy access to a variety of useful 5-substituted isoxazoles

Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.