83279-39-4|3-Chloro-4-(trifluoromethoxy)benzaldehyde| Ambeed

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Quality Control of [ 83279-39-4 ] Purity: 98% SDS Specification

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Product Details of [ 83279-39-4 ]

CAS No. :	83279-39-4
Formula :	C₈H₄ClF₃O₂
M.W :	224.56
SMILES Code :	ClC1=C(C=CC(=C1)C=O)OC(F)(F)F
MDL No. :	MFCD01631561
Boiling Point :	No data available
InChI Key :	SDBUQQVMQXOGBO-UHFFFAOYSA-N
Pubchem ID :	2778891

Safety of [ 83279-39-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 83279-39-4 ]

* 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 [ 83279-39-4 ]

[ 83279-39-4 ] Synthesis Path-Downstream 1~22

1
[ 83279-39-4 ]
[ 1692-25-7 ]
[ 628710-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 40.0h;Nitrogen atmosphere;	A solution of <strong>[83279-39-4]3-chloro-4-trifluoromethoxybenzaldehyde</strong> (3 g, 13.3 mmol) and 3- pyridylboronic acid (1.97 g, 16.0 mmol) in dioxane (70 [ML)] and 2M [K2CO3] (20 mL) is degassed with nitrogen prior to addition of Pd (PPh3) 4 (1.5 g, 1.33 mmol). The mixture was stirred at [100C] under nitrogen for 40 hours, then cooled and filtered on celite/silica and the filtrate concentrated under reduced pressure. The crude was purified by column chromatography (2/1 heptane/ethyl acetate) to give 1.51 g of title compound. [C13H8F3NO2] Mass (calculated): [267]; (found) [[M+H+]] = 268 NMR (400 MHz, [CDCL3] : 7.3-7. 35 [(1H,] m, aryl-H); 7.4-7. 45 [(1H,] m, aryl-H); 7.7-7. 75 [(1H,] m, aryl- H); 7.9-8 (2H, n, aryl-H); 8.65 [(1H,] bs, aryl-H); 8.7 [(1H,] bs, aryl-H).

References: [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 48.

2
[ 83279-39-4 ]
[ 26138-64-7 ]
4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; pyridine;Heating / reflux;	Example 21; Synthesis of the present compound (IIc') [Compound No. (3c-32)]; A mixture of 0.60 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 1.99 g of <strong>[83279-39-4]3-chloro-4-(trifluoromethoxy)benzaldehyde</strong>, 10 ml of pyridine and 88mul of piperidine was heated under refluxing overnight. After cooling to room temperature, 50 ml of water was added to the reaction mixture, and precipitated crystals were filtered, and washed with 40 ml of tetrahydrofuran, and 60 ml of hexane to obtain 0.92 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (3c-32)] as a yellow crystal.

References: [1]Patent: EP1671950,2006,A1 .Location in patent: Page/Page column 73.

3
[ 83279-39-4 ]
[ 771-03-9 ]
4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In chloroform; for 4.0h;Heating / reflux;	Example 1; Synthesis of the present intermediate (II-2a) [Compound No. (1a-6)]; A mixture of 1.85 g of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 2.25 g of <strong>[83279-39-4]3-chloro-4-(trifluoromethoxy)benzaldehyde</strong>, 20 ml of chloroform and 0.7 ml of piperidine was heated under refluxing for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography. Resulting crystals were washed with 40 ml of t-butyl methyl ether to obtain 0.40 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (1a-6]) as a yellow crystal.

References: [1]Patent: EP1671950,2006,A1 .Location in patent: Page/Page column 70.

4
[ 83279-39-4 ]
[ 5501-39-3 ]
4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; pyridine; for 4.0h;Heating / reflux;	Example 15; Synthesis of the present compound (IIa') [Compound No. (3a-32)]; A mixture of 0.50 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone, 0.74 g of <strong>[83279-39-4]3-chloro-4-(trifluoromethoxy)benzaldehyde</strong>, 6 mg of pyridine and 0.1 ml of piperidine was heated under refluxing for 4 hours. After cooled to room temperature, 40 ml of water was added to the reaction mixture, precipitated crystals were filtered, and this was washed with tetrahydrofuran, then with ethyl acetate to obtain 0.41 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (3a-32)] as a yellow crystal.

References: [1]Patent: EP1671950,2006,A1 .Location in patent: Page/Page column 72.

5
[ 83279-39-4 ]
[ 2555-37-5 ]
4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In chloroform; for 2.5h;Heating / reflux;	Example 6; Synthesis of the present intermediate (II-2c) [Compound No. (1c-6)]; A mixture of 2.25 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 2.25 g of <strong>[83279-39-4]3-chloro-4-(trifluoromethoxy)benzaldehyde</strong>, 20 ml of chloroform and 0.7 ml of piperidine was heated under refluxing for 2 hours and 30 minutes. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography. Resulting crystals were washed with 40 ml of t-butyl methyl ether to obtain 1.49 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (1c-6)] was obtained as a yellow crystal.

References: [1]Patent: EP1671950,2006,A1 .Location in patent: Page/Page column 71.

6
[ 83279-39-4 ]
[ 128796-39-4 ]
[ 1252809-21-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5544 - 5547.

7
[ 83279-39-4 ]
[ 1227682-57-6 ]

References: [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 6296 - 6299.

8
[ 83279-39-4 ]
[ 109-77-3 ]
[ 771564-45-5 ]