3356-89-6|5-Chloro-3-phenylisoxazole| Ambeed

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Quality Control of [ 3356-89-6 ] Purity: 97% SDS Specification

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NMR

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Product Details of [ 3356-89-6 ]

CAS No. :	3356-89-6
Formula :	C₉H₆ClNO
M.W :	179.60
SMILES Code :	ClC1=CC(C2=CC=CC=C2)=NO1
MDL No. :	MFCD00046079
InChI Key :	KWVZAEKGUQQYMK-UHFFFAOYSA-N
Pubchem ID :	326080

Safety of [ 3356-89-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 3356-89-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3356-89-6 ]

[ 3356-89-6 ] Synthesis Path-Downstream 1~35

1
[ 75-66-1 ]
[ 3356-89-6 ]
[ 27025-92-9 ]

References: [1]Canadian Journal of Chemistry,1970,vol. 48,p. 1371 - 1376.

2
[ 1076-59-1 ]
[ 3356-89-6 ]

References: [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 3022 - 3034.
[2]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 127 - 134.
[3]Tetrahedron,1970,vol. 26,p. 453 - 465.
[4]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 319 - 323.
[5]Organic and biomolecular chemistry,2020,vol. 18,p. 2283 - 2296.

3
[ 821-09-0 ]
[ 3356-89-6 ]
[ 62847-61-4 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 934 - 939.

4
[ 64-17-5 ]
[ 3356-89-6 ]
[ 23244-34-0 ]

References: [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 3022 - 3034.
[2]Tetrahedron,1970,vol. 26,p. 453 - 465.

5
[ 109-79-5 ]
[ 3356-89-6 ]
[ 25755-81-1 ]

References: [1]Tetrahedron,1970,vol. 26,p. 453 - 465.

6
[ 110-77-0 ]
[ 3356-89-6 ]
[ 62847-62-5 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 934 - 939.

7
[ 3356-89-6 ]
[ 5188-07-8 ]
[ 25755-80-0 ]

References: [1]Tetrahedron,1970,vol. 26,p. 453 - 465.

8
[ 368-39-8 ]
[ 3356-89-6 ]
5-chloro-3-phenyl-2-ethyl-isoxazolium; tetrafluoroborate [ No CAS ]

References: [1]Zeitschrift fur Chemie,1968,vol. 8,p. 170 - 171.

9
[ 3356-89-6 ]
[ 107-18-6 ]
[ 62847-69-2 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 934 - 939.

10
[ 3356-89-6 ]
[ 67-63-0 ]
[ 27025-89-4 ]

References: [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 3022 - 3034.
[2]Canadian Journal of Chemistry,1970,vol. 48,p. 1371 - 1376.

11
[ 3356-89-6 ]
[ 75-08-1 ]
[ 13626-89-6 ]

References: [1]Journal of Heterocyclic Chemistry,1967,vol. 4,p. 54 - 60.

12
[ 3356-89-6 ]
[ 75-65-0 ]
[ 27025-90-7 ]

References: [1]Canadian Journal of Chemistry,1970,vol. 48,p. 1371 - 1376.

13
[ 3356-89-6 ]
[ 71-36-3 ]
[ 23893-62-1 ]

References: [1]Tetrahedron,1970,vol. 26,p. 453 - 465.

14
[ 3356-89-6 ]
[ 27133-14-8 ]

References: [1]Canadian Journal of Chemistry,1970,vol. 48,p. 1371 - 1376.

15
[ 556-52-5 ]
[ 3356-89-6 ]
[ 115697-82-0 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 337 - 342.

16
[ 3356-89-6 ]
[ 100-51-6 ]
[ 94447-61-7 ]

Yield	Reaction Conditions	Operation in experiment
91%		General procedure: To a stirred suspension of NaH (60% in mineral oil, 440 mg, 11 mmol, prewashed with hexane) in anhydrous THF (20 mL) was added the appropriate alcohol (15 mmol) at r.t. and the reaction mixture was stirred for 0.5 h. Next, <strong>[3356-89-6]5-chloro-3-phenylisoxazole</strong> (2) (1.0 g, 5.6mmol) was introduced as a solid and the mixture was refluxed for 1 h. After cooling to r.t., the mixture was quenched with H2O (20 mL). For 4a and 4b, the resulting precipitate was collected, washed with H2O and recrystallized from hexane-Et2O mixture. For 3a, the reaction mixture was extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give isoxazole 3a. 5-tert-Butoxy-3-phenylisoxazole (4c) was synthesized analogously using commercially available potassium tert-butoxide.

References: [1]Synthesis,2017,vol. 49,p. 4478 - 4488.
[2]European Journal of Organic Chemistry,2019,vol. 2019,p. 3022 - 3034.
[3]Tetrahedron Letters,1984,vol. 25,p. 4587 - 4590.

17
[ 3356-89-6 ]
[ 1006-65-1 ]

References: [1]Synthesis,1985,p. 792 - 794.

18
[ 75-35-4 ]
[ 698-16-8 ]
[ 3356-89-6 ]

References: [1]Tetrahedron Letters,1984,vol. 25,p. 4587 - 4590.

19
[ 2415-80-7 ]
[ 3356-89-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With nitrosylsulfuric acid; In nitromethane; at 70 - 75℃; for 3h;	General procedure: A reaction vessel with a magnetic stirrer was charged with reactants in the followingsequence: NOHSO4 (3 mmol), nitromethane (3 ml) and the corresponding1,1-dichlorocyclopropane(1 mmol), then closed with a joint stopper, andplaced in a thermostatic bath. The reaction mixture was vigorously stirredand heated gradually from room temperature up to 70-75 C and thenkept at 70-75 C for 3-4 h. Afterwards, the resulting mixture was passedthrough a layer of SiO2 (40/60), the latter was additionally washed withchloroform (3 × 5 ml). The filtrate was evaporated under reduced pressureto afford the crude product which was recrystallized from ethanol orpurified by column chromatography (Silica gel 40/60, ethyl acetate-lightpetroleum, 1:10). The 1H and 13C NMR spectra of isoxazoles 2a-i, 4b,cand 5b,c were as described elsewhere.14-16

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5229 - 5231.
[2]Mendeleev Communications,2019,vol. 29,p. 419 - 420.
[3]Russian Journal of Organic Chemistry,2013,vol. 49,p. 186 - 194.
Zh. Org. Khim.,2013,vol. 49,p. 198 - 206,9.

22
[ 3529-08-6 ]
[ 3356-89-6 ]
[ 86684-07-3 ]