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
• Article Data: 32

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 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 7145-48-4 Benzoylacetaldehyde ω-oxime 
• 53009-60-2 3-(hydroxyimino-(seqcis))-1-phenyl-propan-1-one 
• 1215-50-5 1-phenyl-3-(phenylamino)prop-2-en-1-one 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 15736-98-8 sodium cyanate 
• 3623-15-2 phenyl propargyl ketone 
• 70820-70-1 3-hydroxyimino-3-phenyl-propionaldehyde oxime 

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 
• 4156-16-5 2-ethyl-5-phenylisoxazolium-3'-sulphonate 
• 3383-40-2 4-nitro-5-(4-nitro-phenyl)-isoxazole 
• 5765-41-3 4-isoxazol-5-ylbenzenesulfonyl chloride 
• 31301-43-6 4-Chloro-5-phenylisoxazole 
• 126633-02-1 5-(3-nitrophenyl)isoxazole 
• 62269-21-0 3-<(trimethylsilyl)oxy>cinnamonitrile 

Relevant articles and documents

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Reactions of Thianthrene Cation Radical with Oximes of Cinnamaldehydes and Unsaturated Aromatic Ketones in Acetonitrile

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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

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.