1011-37-6

Basic information

• Product Name: 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE
• Synonyms: 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE;5-(chloroMethyl)-3-phenyl-1,2-oxazole;Isoxazole, 5-(chloromethyl)-3-phenyl-
• CAS NO: 1011-37-6
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Mol File: 1011-37-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 337.6 °C at 760 mmHg
• Flash Point: 158 °C
• Appearance: /
• Density: 1.222 g/cm³
• Vapor Pressure: 0.000203mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE(1011-37-6)
• EPA Substance Registry System: 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE(1011-37-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 1011-37-6(Hazardous Substances Data)

Usage

General Description

5-(Chloromethyl)-3-phenylisoxazole is a chemical compound with the molecular formula C10H8ClNO. It is an isoxazole derivative with a chloromethyl substitution at position 5 and a phenyl group at position 3. 5-(CHLOROMETHYL)-3-PHENYLISOXAZOLE is used in organic synthesis and medicinal chemistry for the development of new pharmaceuticals and agrochemicals. It has been reported to have antimicrobial and antifungal properties and has been studied for its potential use as an anti-cancer agent. Additionally, 5-(Chloromethyl)-3-phenylisoxazole has been investigated for its ability to inhibit certain enzymes and receptors, making it a valuable tool in biochemical research.

InChI:InChI=1/C10H8ClNO/c11-7-9-6-10(12-13-9)8-4-2-1-3-5-8/h1-6H,7H2

Upstream product

• 873-67-6 benzonitrile oxide 
• 624-65-7 2-propynyl chloride 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 698-16-8 benzohydroximoyl chloride 
• 90924-12-2 3-phenyl-5-hydroxymethylisoxazole 
• 932-90-1 Benzaldoxime 
• 100-52-7 benzaldehyde 
• 934-16-7 phenylhydroxamoyl chloride 
• 932-90-1 syn-benzaldehyde oxime 
• 106-96-7 propargyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 64988-86-9 2,3-dichloropropenyl phenyl ketone 

Downstream Products

• 66046-40-0 5-isothiocyanatomethyl-3-phenylisoxazole 
• 1017-07-8 5-N,N-dimethylaminomethyl-3-phenyl isoxazole 
• 1195982-95-6 (R)-3-(1-phenylcycloheptanecarbonyloxy)-1-(3-phenylisoxazol-5-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195982-91-2 (R)-1-(3-phenylisoxazol-5-ylmethyl)-3-(1-thiophen-2-ylcycloheptanecarbonyloxy)-1-azoniabicyclo[2.2.2]octane chloride 
• 942935-99-1 5-(azidomethyl)-3-phenylisoxazole 
• 54408-35-4 1-(3-phenyl-1,2-oxazol-5-yl)methanamine 
• 339016-92-1 4-chloro-N-((3-phenylisoxazol-5-yl)methyl)benzenesulfonamide 
• 852431-00-6 N-methyl(3-phenylisoxazol-5-yl)methanamine 
• 942519-70-2 2-(3-phenylisoxazol-5-ylmethylamino)ethanol 
• 69337-36-6 acetic acid (3-phenyl-5-isoxazolyl)methyl ester 
• 68870-55-3 5-(methoxymethyl)-3-phenylisoxazole 
• 1201042-04-7 (R)-1-(3-phenyl-isoxazol-5-ylmethyl)-3-((S)-2-phenyl-2-piperidin-1-yl-propionyloxy)-1-azonia-bicyclo[2.2.2]octane choride 

Relevant articles and documents

A Simplified Synthesis of Unsaturated Nitrogen-Heterocycles using Nitrile Betaines

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Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link

A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,?- and ?-halo-?,?-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl.

Lead Optimization Generates CYP11B1 Inhibitors of Pyridylmethyl Isoxazole Type with Improved Pharmacological Profile for the Treatment of Cushing's Disease

Cushing's disease, characterized by elevated plasma cortisol levels, can be controlled by inhibition of 11β-hydroxylase (CYP11B1). The previously identified selective and potent CYP11B1 inhibitor 5-((5-methylpyridin-3-yl)methyl)-2-phenylpyridine Ref 7 (IC50= 2 nM) exhibited promutagenic potential as well as very low oral bioavailability in rats (F = 2%) and was therefore modified to overcome these drawbacks. Successful lead optimization resulted in similarly potent and selective 5-((5-methoxypyridin-3-yl)methyl)-3-phenylisoxazole 25 (IC50 = 2 nM, 14-fold selectivity over CYP11B2), exhibiting a superior pharmacological profile with no mutagenic potential. Furthermore, compound 25 inhibited rat CYP11B1 (IC50 = 2 μM) and showed a high oral bioavailability (F = 50%) and sufficient plasma concentrations in rats, providing an excellent starting point for a proof-of-principle study.