Name: 582-65-0|3-(4-Fluorobenzoyl)-1,1,1-trifluoroacetone|95%
Brand: Ambeed
SKU: A901236
Price: 16.0 USD
Availability: InStock
Rating: 95 (35 reviews)

1
[ 383-63-1 ]
[ 403-42-9 ]
[ 582-65-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium methylate; In tert-butyl methyl ether; at 20℃; for 3h;	a) 4,4,4-Trifluoro-1-(4-fluoro-phenyl)-butane-1,3-dione To a solution of ethyl trifluoroacetate (23.9 mL, 199 mmol) in TBME (230 mL) containing sodium methoxide (5.4 M, 39.6 mL, 214 mmol) was added 4-fluoroacetophenone (25 g, 181 mmol) and the resulting mixture stirred at room temperature for 3 h and then poured into ice-water. The mixture was then diluted with HCl (2 N, 200 mL) and then extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulfate and evaporated to afford the title compound (40.9 g, 97%) which was obtained as an orange oil. MS: m/e=232.9 [M-H]-.
97%	With sodium methylate; In tert-butyl methyl ether; at 20℃; for 3h;	To a solution of ethyl trifluoroacetate (23.9 mL, 199 mmol) in tertbutylmethylether (230 mL) containing sodium methoxide (5.4 M, 39.6 mL, 214 mmol) was added 4-fluoroacetophenone (25 g, 181 mmol) and the resulting mixture stirred at room temperature for 3 h and then poured into ice-water. The mixture was then diluted with HCl (2 N, 200 mL) and then extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulfate and evaporated to afford the title compound (40.9 g, 97%) which was obtained as an orange oil. MS: m/e=232.9 [M-H]-.
95%	With sodium methylate; In ethanol; at 20℃; for 3h;	General procedure: 40-chloroacetophenone (0.50 mL, 3.86 mmol)was added to a solution of ethyl trifluoroacetate (0.5 mL,4.20 mmol) containing 5.4M sodium methoxide (0.8 mL,4.60 mmol) in ethanol (8.0 mL). The reaction mixture was stirred atroom temperature for 3 h, after which the mixturewas diluted withcold water and 2 N HCl (5.0 mL). The resulting mixture was left tostand overnight to obtain a precipitate. The precipitatewas filtered,washed with cold water and air dried to give the pure compound.

90%	With sodium; In methanol; for 24h;Reflux;	Add 4.5 g of metallic sodium to 70 ml of anhydrous methanol.After the reaction is completed, it is cooled to room temperature.14 g of p-fluoroacetophenone and 17 g (120 mmol) of ethyl trifluoroacetate were slowly added.After the dropwise addition was completed, the temperature was refluxed for 24 hours, and concentrated to a yellow viscous liquid.Add 2mol/L hydrochloric acid to adjust the pH to 2~3, extract with ethyl acetate.Drying with magnesium sulfate,After distilling off the solvent, a yellow oil was obtained.1-p-fluoro-4,4,4-trifluorobutan-1,3dione 21 g, yield 90%.
73%	With sodium; In ethanol; toluene; at 60℃; for 6h;	100 mL of toluene and absolute ethanol (16.56 g, 0.36 mol) were placed in a vessel to give a mixture B; the chopped sodium metal (8.288, 0.36 mmol) was placed in a vessel containing mixture 8 and stirred until the container (41.48, 0.3 mmol) and ethyl trifluoroacetate (51.128, 0.36 mmol) were placed in a vessel to give a mixture C; and the mixture was cooled to & lt; RTI ID = 0.0 & gt; The container is placed in an electric heating device and gradually heated to 60 C within 30 minutes. After 6 hours of reaction, distillation, extraction, washing, organic phase and drying are carried out to obtain mixture D; The extraction was repeated three times with ethyl acetate, and the washing was repeated twice; the drying was carried out using anhydrous sodium sulfate. The mixture D was subjected to distillation under reduced pressure and allowed to stand under cooling condition. A white solid was precipitated, filtered and dried to give intermediate 1-p-fluorophenyl-4,4,4-trifluorobutanedione; the product The mass of 1-p-fluorophenyl_4,4,4-trifluorobutanedione was 51.245g. Yield: 73.00%.
73%	In ethanol; toluene; at 60℃; for 6h;	100 ml of toluene and absolute ethanol (16.56 g, 0.36 mol)Placed in a container to give a mixture B; 2.2)The chopped metal will be sodium(8.28 g, 0.36 mol) was placed in a vessel containing mixture B,Stirring to the vesselA white powder appeared,And no sodium surplus,Placing the container under cooling conditions;2.3) A solution of p-fluoroacetophenone (41.48, 0.3andEthyl trifluoroacetate (51.128, 0.36111 O1)Placed in a containerTo obtain a mixture C;2.4) The container is placed in an electrothermal device,In the range of 30 minutesGradually heated to 60 C, 6 hours after the reactionExtracting, washing, combining organic phase and drying process to obtain mixture D;[0042] Said extraction is referred to as extraction with ethyl acetate, and the extraction process is repeated three times; the water washing process is repeated 2; And the drying process is drying using anhydrous sodium sulfate.2.5) The mixture D was subjected to distillation under reduced pressure and allowed to stand under cooling, whereupon a white solid precipitated and was filtered off, driedDried to give intermediate 1-p-fluorophenyl-4,4,4-tetrafluorobutanedione;The mass of the product 1-p-fluorophenyl-4,4,4-trifluorobutanedione was 51.245 g. Yield: 73.00
73%	With sodium; In ethanol; toluene; at 60℃; for 6.5h;	100 mL of toluene and anhydrous ethanol (16.56 g, 0.36 mol) was placed in a vessel to give a mixture B;The chopped metal sodium (8.288, 0.36 mol) was placed in a vessel containing the mixture 8, After stirring to a white powder in the container and leaving sodium free, place the container under cooling conditions; A mixture of p-fluoroacetophenone (41.48, 0.3 mol) and ethyl trifluoroacetate (51.128, 0.36 mol) was placed in a vessel to give a mixture C; The container was placed in an electric heating device and gradually heated to 60 C in the range of 30 minutes. After 6 hours of reaction, the mixture was subjected to distillation under reduced pressure, extracted, washed with water, and the organic phase was combined to dry the mixture. The extraction is referred to as using ethyl acetate and the extraction process is repeated three times; the washing process is repeated twice; the drying process is carried out using anhydrous sodium sulfate. The mixture D was distilled under reduced pressure and allowed to stand under cooling. The white solid was precipitated and filtered and dried to give intermediate 1-p-fluorophenyl-4,4,4-trifluorobutanedione; The mass of the product 1-p-fluorophenyl-4,4,4-trifluorobutanedione was 51.245 g. Yield: 73.00%.
73%	With sodium; In ethanol; toluene; at 60℃; for 6.5h;	2.1) 100 mL of toluene and absolute ethanol (16.56 g, 0.36 mol) were placed in a vessel to give mixture B;2.2) The chopped metal sodium (8.28 g, 0.36 mol)Placed in a container containing the mixture B,Stir to the container to appear white powder,And the sodium is left behind, the container is placed under cooling conditions;2.3) A solution of p-fluoroacetophenone (41.4 g, 0.3 mol)And ethyl trifluoroacetate (51.12 g, 0.36 mol) were placed in a vessel,To obtain a mixture C;2.4) Place the container in an electric heating device,In the 30-minute range gradually heated to 60C ,After 6 hours of reaction,Vacuum distillation, extraction, washing,The organic phase was combined and the drying was carried out to give the mixture D;The extraction is referred to as using ethyl acetate,And the extraction process was repeated 3 times;The washing process is repeated twiceThe drying process is carried out using anhydrous sodium sulfate.2.5) The mixture D was subjected to distillation under reduced pressure and allowed to stand under cooling conditions,Precipitate the white solid after filtration, dry,To give intermediate 1-(4-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione;The mass of the product 1-(4-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione was 51.245 g.Yield: 73.00%.
73%	With sodium; In toluene; at 60℃; for 6.5h;	2.1) 100 mL of toluene and absolute ethanol (16.56 g, 0.36 mol) were placed in a vessel to give mixture B;2.2) The chopped metal sodium (8.28 g, 0.36 mol) was placed in a vessel containing the mixture B, stirred to a white powder in the vessel and left without sodium. The vessel was placed under cooling conditions;2.3) A mixture of p-fluoroacetophenone (41.4 g, 0.3 mol) and ethyl trifluoroacetate (51.12 g, 0.36 mol) was placed in a vessel to give a mixture C;2.4) The container was placed in an electric heating device and gradually heated to 60 C over a period of 30 minutes,After 6 hours of reaction,Carrying out vacuum distillation, extracting, washing with water, combining the organic phase and drying to obtain the mixture D; the extraction is referred to as using ethyl acetate,And the extraction process was repeated 3 times;The washing process is repeated twiceThe drying process is carried out using anhydrous sodium sulfate.2.5) The mixture D was subjected to distillation under reduced pressure and allowed to stand under cooling. The white solid was precipitated and filtered, driedTo give the intermediate 1-p-fluorophenyl-4,4,4-trifluorobutanedione;The mass of the product 1-p-fluorophenyl-4,4,4-trifluorobutanedione was 51.245 g.Yield: 73.00%.
73%	With sodium; In ethanol; toluene; at 60℃; for 6.5h;	2.1) Place 100 mL of toluene and absolute ethanol (16.56 g, 0.36 mol) in a vessel to obtain a mixture B1;2.2) Chopped sodium metal (8.28 g, 0.36 mol) was placed in a vessel filled with mixture B1, stirred into a vesselIn the white powder appears, and no sodium surplus, the container is placed under cooling conditions;2.3) P-fluoroacetophenone (41.4 g, 0.3 mol) and ethyl trifluoroacetate (51.12 g, 0.36 mol) were placed in a vesselTo obtain a mixture C1;2.4) The container is placed in an electric heating device, gradually warmed to 60 C within 30 minutes, and after 6 hours of reactionVacuum distillation, extraction, washed with water, the combined organic phase, the drying process to obtain a mixture D1;The extraction was referred to as extraction with ethyl acetate, and the extraction process was repeated 3 times; the washing process was repeated 2Times; the drying process is drying with anhydrous sodium sulfate.2.5) After the mixture D1 was distilled under reduced pressure and allowed to stand under cooling, the white solid was precipitated, filtered, driedDrying to give the intermediate 1-p-fluorophenyl-4,4,4-trifluorobutane dione;The mass of 1-p-fluorophenyl-4,4,4-trifluorobuten dione was 51.245 g. Yield: 73.00%.
73%	With sodium; In ethanol; toluene; at 60℃; for 6.5h;	2.1) 100 mL of toluene and absolute ethanol (16.56 g, 0.36 mol) were placed in a vessel to obtain a mixture B;2.2) Chopped sodium metal (8.28 g, 0.36 mol) was placed in a vessel with mixture B and stirred into the vesselAfter a white powder appears and there is no sodium remaining, the container is placed under cooling conditions;2.3) P-fluoroacetophenone (41.4 g, 0.3 mol) and ethyl trifluoroacetate (51.12 g, 0.36 mol) were placed in a vesselTo obtain a mixture C;2.4) The container is placed in an electric heating device, gradually warmed to 60 C within 30 minutes, and after 6 hours of reactionLine vacuum distillation, extraction, washing, combined organic phase, the drying process, to obtain a mixture D;The extraction was referred to as extraction with ethyl acetate, and the extraction process was repeated 3 times; the washing process was repeated 2Times; the drying process is drying with anhydrous sodium sulfate.2.5) After the mixture D was distilled under reduced pressure and allowed to stand under cooling, the white solid precipitated, filtered and driedDrying to give the intermediate 1-p-fluorophenyl-4,4,4-trifluorobutane dione;The mass of 1-p-fluorophenyl-4,4,4-trifluorobuten dione was 51.245 g. Yield: 73.00%.
67%	With sodium methylate; In benzene; at 50℃; for 8.25h;	General procedure: 4-Methoxyacetophenone (3.0 g, 20 mmol) and sodium methoxide (2.16 g, 40 mmol) were added into 80 ml dry benzene, and the mixture was stirred for 15 min. To this mixture ethyl trifluoroacetate (5 ml, 42 mmol) was added dropwise, and then stirred at 50 C for 8 h. The resulting mixture was cooled to the room temperature and acidified with dilute hydrochloric acid. The organic layer was collected, washed with a saturated NaHCO3 solution and dried over anhydrous MgSO4. The organic solvent was removed by rotary evaporation. The residuewas recrystallized with ethanol to give the light yellow crystal TMPD in yield 70%.
		Ethyl trifluoroacetate (2.35 g, 1.66 mmol) was placed in a 50 mL round bottom flask, and dissolved in methyl tert-butyl ether (7.5 mL). To the stirred solution was added 25 weight % sodium methoxide (4.0 mL, 17.7 mmol) via an addition funnel over a 2 minute period. Next, 4'-fluoroacetophenone (2.1 g, 15 mmol) was dissolved in methyl tert-butyl ether (2 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (15.75 hours), 3N HCl (7.0 mL) was added. The organic layer was collected, washed with brine (7.5 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 3.2 g of pale-orange solid. The solid was recrystallized from iso-octane to give 2.05 g of the dione.
	With sodium methylate; In tetrahydrofuran; methanol; at 0 - 20℃;	General procedure: To a freshly prepared sodium methylate solution in methanol and THF ethyl trifluoroacetate (1.2 equiv) was added under stirring at 0 followed by addition of ketone 2 (1.0 equiv). The reaction mixture was allowed to stir for additional 3-24 h until the starting materials were consumed, as determined by thin-layer chromatography (TLC). Then the solvent was removed under reduced pressure and the residue was acidified with hydrochloric acid (1 N), followed by extracted with acetic ether. The combined organic layers were dried (MgSO4), Fitered and the filtrate was concentrated under reduced pressure. The crude product was puried by column chromatography. Yield: 40-90%. For some cases, the crude products can be straight used for step c without the column chromatography procedure.
	With sodium methylate; In methanol; for 2h;Reflux;	General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained.
	With ethanol; sodium;Inert atmosphere; Reflux;	General procedure: Sodium (1.5equiv) was dissolved under inert conditions in 3-5ml absolute ethanol, and ethyl trifluoroacetate (2equiv) (diluted in absolute ethanol) was added. Afterwards, a suitable acetophenone (1equiv), dissolved in absolute ethanol, was added. The reaction mixture was heated under reflux conditions overnight and cooled to room temperature. Quenching was performed using hydrochloride acid (1N), and the mixture was stirred for 15min. After extraction with ethyl acetate, the combined organic phases were washed with brine. The organic layer was dried over MgSO4, filtrated and the solvent was removed under reduced pressure. The greasy residue was used without any further purification.
2.10 g		To a stirred solution of 4-fluoroacetophenone (1.02 g, 7.38 mmol) in anhydrous THF (10 mL) was added sodium hydride (60% w/w, 886 mg, 22.15 mmol) portion wise at RT. The mixture was stirred for 30 min, to it was added ethyl acetate (3.0 mL, 29.5 mmol) and it was further stirred at 40 C for 3 h. The mixture was cooled to RT, quenched with IN HC1 and extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude compound obtained was purified by silica gel column chromatography to yield 813 mg of the desired product; 1H NMR (300 MHz, CDC13) delta 2.19 (s, 3H), 6.13 (s, 1H), 7.12 (t, = 8.4 Hz, 2H), 7.89 (t, = 5.4 Hz, 2H), 16.16 (br s, 1H).
	With sodium; In tetrahydrofuran;Cooling with ice;	General procedure: P-fluoroacetophenone (0.69 g, 5 mmol) or p-bromoacetophenone (0.99 g, 5 mmol) and ethyl trifluoroacetate (1.42 g, 10 mmol) were placed in a 50 mL round bottom flask and placed in an ice bath. 30 mL of anhydrous tetrahydrofuran was added, followed by taking (0.69 g, 30 mmol) of sodium, and cutting into fine sodium scraps, slowly adding them to a round bottom flask, and stirring, overnight. Check for residual sodium and, if any, pour the reaction into absolute ethanol to completely remove residual sodium. If there is no residual sodium beads, dilute all the solvent under reduced pressure, add 20mL of water, then add hydrochloric acid solution to acidify to pH = 2 ~ 3, then add 50mL CH2Cl2, wash with water (30mL × 3), saturated brine (30mL × 2) The organic layer was dried over anhydrous Na2SO4 . The CH2Cl 2 was distilled off, and column chromatography was carried out using petroleum ether: ethyl acetate = 10:1, 10:1 (Rf = 0.3) as eluent, respectively, to obtain red solid 4 and white solid 7 respectively, yield 80%.
		General procedure: To a tetrahydrofuran solution of acetophenones (100mmol) was added NaH (200mmol), and the mixture was stirred for 5min. Ethyl trifluoroacetate (250mmol) was then added. The reaction mixture was stirred at room temperature for 4h and neutralized with 2N HCl. The precipitate formed was collected, washed with methanol and dried, which was directly used for the next step without further purification.

Reference： [1]Patent: US2009/5370,2009,A1 .Location in patent: Page/Page column 16
[2]Patent: US2009/143371,2009,A1 .Location in patent: Page/Page column 39
[3]Journal of Molecular Structure,2020,vol. 1202
[4]Patent: CN108849912,2018,A .Location in patent: Paragraph 0016
[5]Organic Process Research and Development,2019,vol. 23,p. 1892 - 1899
[6]Synthesis,1997,p. 1321 - 1324
[7]Patent: CN105884783,2016,A .Location in patent: Paragraph 0054; 0055; 0056; 0057; 0058; 0059; 0060; 0061
[8]Patent: ,2016, .Location in patent: Paragraph 0037;0043
[9]Patent: CN105949202,2016,A .Location in patent: Paragraph 0054-0061
[10]Patent: CN106008517,2016,A .Location in patent: Paragraph 0054; 0055; 0056; 0057; 0058; 0059; 0060; 0061
[11]Patent: CN106008519,2016,A .Location in patent: Paragraph 0054; 0055; 0056; 0057; 0058; 0059; 0060; 0061
[12]Patent: CN105949200,2016,A .Location in patent: Page/Page column 7; 23
[13]Patent: CN105949201,2016,A .Location in patent: Paragraph 0054-0061
[14]Dyes and Pigments,2016,vol. 132,p. 398 - 404
[15]Tetrahedron,2009,vol. 65,p. 2124 - 2135
[16]Journal of the American Chemical Society,1950,vol. 72,p. 2948,2949
[17]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365
[18]Journal of Fluorine Chemistry,2002,vol. 118,p. 135 - 147
[19]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 499 - 504
[20]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 95 - 98
[21]Journal of Fluorine Chemistry,2006,vol. 127,p. 780 - 786
[22]Patent: US2005/222240,2005,A1 .Location in patent: Page/Page column 4
[23]Journal of Fluorine Chemistry,2010,vol. 131,p. 584 - 586
[24]Dalton Transactions,2010,vol. 39,p. 9000 - 9007
[25]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4653 - 4660
[26]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1581 - 1588
[27]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3076 - 3080
[28]Molecules,2016,vol. 21
[29]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5717 - 5729
[30]Patent: WO2017/21879,2017,A1 .Location in patent: Page/Page column 66
[31]European Journal of Medicinal Chemistry,2018,vol. 155,p. 545 - 551
[32]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3406 - 3413
[33]Patent: CN109438365,2019,A .Location in patent: Paragraph 0062-0065
[34]Bioorganic Chemistry,2020,vol. 97

2
[ 582-65-0 ]
[ 70862-56-5 ]

Reference： [1]Pharmazie,1979,vol. 34,p. 68 - 69

3
[ 582-65-0 ]
[ 73418-35-6 ]

Reference： [1]Pharmazie,1979,vol. 34,p. 568 - 568

4
[ 4930-98-7 ]
[ 582-65-0 ]
2-[5-(4-Fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

5
[ 15108-18-6 ]
[ 582-65-0 ]
[ 120513-35-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1641 - 1643

6
[ 28710-97-6 ]
[ 582-65-0 ]
7-(4-Fluoro-phenyl)-1-phenyl-5-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-2-one [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 1180 - 1181

7
[ 14889-08-8 ]
[ 582-65-0 ]
7-(4-Fluoro-phenyl)-9-trifluoromethyl-12-thia-6b,10,11-triaza-naphtho[2,1-a]azulene [ No CAS ]

Reference： [1]Heterocycles,1981,vol. 16,p. 1077 - 1080

8
[ 582-65-0 ]
[ 124-46-9 ]
2-amino-4(4'-fluorophenyl)-6-trifluoromethylpyrimidine [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1993,vol. 63,p. 265 - 270

9
[ 582-65-0 ]
[ 137-07-5 ]
[ 77086-78-3 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3795 - 3796

10
[ 582-65-0 ]
[ 828-73-9 ]
2-pentafluorophenyl-3-(4'-fluorophenyl)-5-trifluoromethylpyrazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1993,vol. 63,p. 265 - 270

11
[ 582-65-0 ]
[ 622-88-8 ]
[ 188817-22-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

12
[ 582-65-0 ]
[ 17852-52-7 ]
[ 170569-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 20h;Heating / reflux;	4-Sulphonamidophenyl hydrazine hydrochloride (982 mg, 4.4 mmol) was added to a stirred solution of 4,4,4-trifluoro-1-[4-(fluoro)phenyl]-butane-1,3-dione (0.936 g, 4.0 mmol) in ethanol (50 mL). The reaction was heated to reflux and stirred for 20 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The residue was taken up in ethyl acetate and washed with water and brine and dried over MgSO4, filtered, and concentrated in vacuo to give a brown solid which was recrystallized from ethyl acetate and iso-octane to give the 4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide, 0.8 g. 1H NMR (CDCl3): delta 7.92, 7.47, 7.22, 7.09, 6.76, 4.92. MS m/e ES-(M-H) 384 m.p. 167-171 C.

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 1892 - 1899
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365
[3]Patent: US2005/222240,2005,A1 .Location in patent: Page/Page column 4-5

13
[ 582-65-0 ]
[ 100-16-3 ]
[ 188817-07-4 ]

Yield	Reaction Conditions	Operation in experiment
613 mg	In 2,2,2-trifluoroethanol;	The titled compound was prepared by the reaction of Step 1 intermediate (1.02 g, 4.35 mmol) with 4-nitrophenylhydrazine (667 mg, 4.35 mmol) in 2,2,2-trifluoroethanol (10 mL) as per the procedure described in Step 2 of Intermediate 22 to yield 613 mg of the product; 1H NMR (300 MHz, CDCI3) delta 6.77 (s, 1H), 7.10 (t, / = 8.4 Hz, 2H), 7.23 (t, = 4.8 Hz, 2H), 7.50 (d, = 8.7 Hz, 2H), 8.24 (d, = 8.4 Hz, 2H).

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365
[2]Patent: WO2017/21879,2017,A1 .Location in patent: Page/Page column 66-67

14
[ 1118-61-2 ]
[ 582-65-0 ]
3-cyano-6-(4-fluorophenyl)-2-methyl-4-trifluoromethylpyridine [ No CAS ]

Reference： [1]Synthesis,1997,p. 1321 - 1324

15
[ 582-65-0 ]
[ 626-34-6 ]
6-(4-Fluoro-phenyl)-2-methyl-4-trifluoromethyl-nicotinic acid ethyl ester [ No CAS ]

Reference： [1]Synthesis,1997,p. 1321 - 1324

Yield	Reaction Conditions	Operation in experiment
		Step 2. Preparation of 1-(4-fluorophenyl)-4,4,4-trifluoro-1,3-butanedione. To a mixture of 1.15 g (5 mmol) of the intermediate of Step 1, 20 mL of ether and 6 mL of concentrated hydrochloric acid with 10 mL of water was stirred at room temperature for 20 hours. The ether layer was separated, dried over magnesium sulfate and concentrated to give Step 2 intermediate.

17
[ 63211-98-3 ]
[ 582-65-0 ]
(Z)-4-[(Z)-4-Amino-2-chloro-6-methyl-pyrimidin-5-ylimino]-1,1,1-trifluoro-4-(4-fluoro-phenyl)-but-2-en-2-ol [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 191 - 194

18
[ 582-65-0 ]
[ 100-63-0 ]
[ 515845-17-7 ]

Reference： [1]Journal of Fluorine Chemistry,2002,vol. 118,p. 135 - 147
[2]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1003 - 1014

19
[ 582-65-0 ]
2-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride [ No CAS ]
2-[3-(4-fluoro-phenyl)-5-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine [ No CAS ]
2-[5-(4-Fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 95 - 98

20
[ 582-65-0 ]
4-hydrazino-2-hydroxymethyl-1-benzenesulfonamide hydrochloride [ No CAS ]
4-[5-(4-fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 499 - 504

21
[ 582-65-0 ]
[ 59-88-1 ]
[ 515845-17-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5273 - 5280

22
[ 582-65-0 ]
[ 100-16-3 ]
1-(p-nitrophenyl)-3-(p-fluorophenyl)-5-hydroxy-5-trifluoromethyl-Δ²-pyrazoline [ No CAS ]
[ 188817-07-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1003 - 1014

23
[ 582-65-0 ]
[ 371-40-4 ]
1-(p-fluorophenyl)-2-(p-fluorophenyldiazo)-4,4,4-trifluorobutane-1,3-dione [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 880 - 888

24
[ 582-65-0 ]
3-(p-fluorophenyl)-5-hydroxy-5-trifluoromethylisoxazoline [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 880 - 888

25
[ 582-65-0 ]
3-(p-fluorophenyl)-4-(p-fluorophenyldiazo)-5-hydroxy-5-trifluoromethylisoxazoline [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 880 - 888

26
[ 582-65-0 ]
[ 187812-17-5 ]

Reference： [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 880 - 888

27
[ 582-65-0 ]
1-(p-nitrophenyl)-3-(p-fluorophenyl)-5-trifluoromethyl-pyrazole [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1003 - 1014

28
[ 582-65-0 ]
3-[5-(4-fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5273 - 5280

29
[ 582-65-0 ]
3-[5-(4-fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonyl azide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5273 - 5280

30
[ 582-65-0 ]
[ 188817-21-2 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

31
[ 582-65-0 ]
N-[4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]methanesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

32
[ 582-65-0 ]
2,2,2-trifluoro-1-[4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

33
[ 582-65-0 ]
2-[4-Bromo-5-(4-fluoro-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

34
[ 582-65-0 ]
(E)-3-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-propenal [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

35
[ 582-65-0 ]
(E)-3-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-prop-2-en-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

36
[ 582-65-0 ]
(E)-3-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

37
[ 582-65-0 ]
(E)-7-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-3,5-dihydroxy-hept-6-enoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

38
[ 582-65-0 ]
<4α,6β(E)>-6-<2-<1-(2-pyridinyl)-5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl>ethenyl>tetrahydro-4-hydroxy-2H-pyran-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

39
[ 582-65-0 ]
(E)-7-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

40
[ 582-65-0 ]
(E)-7-[5-(4-Fluoro-phenyl)-1-pyridin-2-yl-3-trifluoromethyl-1H-pyrazol-4-yl]-5-hydroxy-3-oxo-hept-6-enoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2095 - 2103

41
[ 582-65-0 ]
[ 100-63-0 ]
5-(4-fluorophenyl)-1-phenyl-3-trifluoromethylpyrazole [ No CAS ]

Reference： [1]International Journal of Chemical Kinetics,2008,vol. 40,p. 370 - 383

42
[ 110-89-4 ]
[ 582-65-0 ]
[ 10025-76-0 ]
C₅H₁₀NH₂⁽¹⁺⁾*Eu(C₁₀H₅F₄O₂)4^(1-)=C₅H₁₀NH₂{Eu(C₁₀H₅F₄O₂)4} [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1967,vol. 29,p. 715 - 723

43
{Fe(1,2-bis(salicylideneaminato)ethane)Cl} [ No CAS ]
[ 582-65-0 ]
(CF₃COCHCO(4-FC₆H₄))(N,N'-ethylenebis(salicylideneiminato))Fe(III) [ No CAS ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1986,vol. 16,p. 1197 - 1206

44
sodium tris(carbonato)cobaltate(III) trihydrate [ No CAS ]
[ 582-65-0 ]
{Co(CF₃C(O)CHC(O)C₆H₄F)3} [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1987,vol. 26,p. 877 - 879

45
[ 1094215-76-5 ]
[ 582-65-0 ]
Co⁽³⁺⁾*CF₃COCHCOC₆H₄F^(1-)*(C₆H₄(O)CHNCH₂)2^(2-)={Co(CF₃C(O)CHC(O)C₆H₄F)((C₆H₄(O)CHNCH₂)2)} [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1987,vol. 26,p. 877 - 879

46
gallium(III) oxide [ No CAS ]
[ 582-65-0 ]
Ga(FC₆H₄COCHCOCF₃)3 [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1981,vol. 43,p. 3412 - 3414

47
indium(III) oxide [ No CAS ]
[ 582-65-0 ]
In(FC₆H₄COCHCOCF₃)3 [ No CAS ]

Reference： [1]Journal of Inorganic and Nuclear Chemistry,1981,vol. 43,p. 3412 - 3414

48
sodium hexachlorodipalladate [ No CAS ]
[ 582-65-0 ]
[ 98292-89-8 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1985,vol. 24,p. 527 - 528

49
[ 7784-27-2 ]
[ 582-65-0 ]
[ 78407-61-1 ]

Reference： [1]Inorganica Chimica Acta,1981,vol. 49,p. 17 - 20

50
zirconium(IV) nitrate pentahydrate [ No CAS ]
[ 582-65-0 ]
Zr((FC₆H₄)COCHCO(CF₃))4 [ No CAS ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1982,vol. 12,p. 671 - 680

51
[ 582-65-0 ]
[ 996-82-7 ]
[ 1037590-07-0 ]

Yield	Reaction Conditions	Operation in experiment
39%		General procedure: A mixture of the corresponding 1-aryl-4,4,4-trifluorobutane-1,3-dione 8 (0.16mol), PCl5 (37.1g, 0.18mol)and CCl4 (10mL) was stirred at 25-35C for several hours. After complete conversion as indicated by 19F NMR, volatile components were removed under reduced pressure. The residue was diluted with dry CH2Cl2 (100mL), cooled to -50C and quenched with a cooled to -50C suspension of sodium diethyl malonate (0.72mol) in absolute ethanol (450mL). After achieving 0C, the reaction was left under stirring for 1h at this temperature. The dark red reaction mixture was quenched with 10% H2SO4 (1.5L) and the organic layer was washed once with water, distilled under reduced pressure and crystallized from ethanol (cooling to -30C) to afford pure 6.

Reference： [1]Organic Letters,2008,vol. 10,p. 2857 - 2859
[2]Tetrahedron,2014,vol. 70,p. 60 - 66
[3]Tetrahedron,2014,vol. 70,p. 8863 - 8871

52
[ 27607-77-8 ]
[ 582-65-0 ]
C₁₃H₁₄F₄O₂Si [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 2124 - 2135

53
[ 582-65-0 ]
[ 17356-08-0 ]
[ 1205603-31-1 ]

Yield	Reaction Conditions	Operation in experiment
		A. (2-Amino-4-trifluoromethyl-thiazol-5-yl)-(4-fluoro-phenyl)-methanoneA mixture of 4,4,4-Trifluoro-1-(4-fluoro-phenyl)-butane-1,3-dione (15 g, 64 mmol) and NBS (11.4 g, 64.1 mmol) was ground together at RT, which incited to give a homogeneous mixture and then solidified to give crude brominated product. Water was added to rinse the solid. The solid was taken up in ethanol (50 mL), and thiourea (4.9 g, 64 mmol) was added. The mixture was heated at 85 C. for 4 h, cooled to RT and partitioned between ethyl acetate and aq. K2CO3. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 291.0 (MH+).

Reference： [1]Patent: US2010/22513,2010,A1 .Location in patent: Page/Page column 39

54
[ 582-65-0 ]
5-(4-fluoridophenyl)-3-(trifluoridomethyl)-1H-pyrazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2010,vol. 131,p. 584 - 586

55
[ 3240-34-4 ]
[ 582-65-0 ]
[ 366-78-9 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 294 - 298

56
[ 582-65-0 ]
[ 62-53-3 ]
PhN=C(CF₃)CHC(p-FPh)OH [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 9000 - 9007

57
[ 582-65-0 ]
[ 310451-83-3 ]

Reference： [1]Journal of the Korean Chemical Society,2011,vol. 55,p. 719 - 722
[2]Journal of Chemical Research,2015,vol. 39,p. 4 - 6
[3]Journal of Chemical Research,2016,vol. 40,p. 107 - 109
[4]Patent: CN105884783,2016,A
[5]Patent: CN105949202,2016,A
[6]Patent: CN106008517,2016,A
[7]Patent: CN105949199,2016,A
[8]Patent: CN105949200,2016,A
[9]Patent: CN105949201,2016,A

58
[ 582-65-0 ]
[ 310451-82-2 ]

Reference： [1]Journal of the Korean Chemical Society,2011,vol. 55,p. 719 - 722

59
[ 582-65-0 ]
[ 6994-25-8 ]
[ 333761-24-3 ]

Reference： [1]Journal of the Korean Chemical Society,2011,vol. 55,p. 719 - 722

60
[ 582-65-0 ]
5-amino-2H-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
[ 333761-06-1 ]

Reference： [1]Journal of the Korean Chemical Society,2011,vol. 55,p. 719 - 722

61
[ 582-65-0 ]
[ 4392-54-5 ]
[ 170569-88-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4653 - 4660

62
1,1,1-trifluoro-4-(4-fluorophenyl)-4-methoxybut-3-en-2-one [ No CAS ]
[ 582-65-0 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 7112 - 7119

63
[ 582-65-0 ]
[ 1353056-08-2 ]
[ 1353056-02-6 ]
[ 1353056-10-6 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 3757 - 3766

64
[ 582-65-0 ]
[ 1430228-92-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 508 - 514

65
[ 582-65-0 ]
[ 1430228-93-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 508 - 514

66
[ 582-65-0 ]
[ 79-19-6 ]
[ 941866-18-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 508 - 514

67
[ 64-17-5 ]
[ 582-65-0 ]
cobalt acetate tetrahydrate [ No CAS ]
C₂₀H₁₀CoF₈O₄*2C₂H₆O [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2630 - 2637

68
[ 582-65-0 ]
[ 2863-98-1 ]
[ 1447577-78-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; for 7h;Reflux;	General procedure: To a warm ethanolic solution (10mL) of 4-hydrazinylbenzonitrile hydrochloride 4 (350mg, 2.0mmol) was added appropriate trifluoromethyl-beta-diketone 5a-5i (2.0mmol) while stirring and the contents were refluxed for 7h. The progress of the reaction was monitored by TLC. When the reaction was completed, excess solvent was evaporated to reduce the volume to one half whereupon reaction mixture was allowed to cool to 20-25C and the solid thus obtained was filtered to obtain 2a-2i (85-93%).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4581 - 4590

69
[ 582-65-0 ]
[ 371-40-4 ]
1-(p-fluorophenyl)-2-(p-fluorophenyldiazo)-4,4,4-trifluorobutane-1,3-dione [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 5890 - 5900

70
[ 23906-13-0 ]
[ 582-65-0 ]
1-(4,6-dimethylpyrimidin-2-yl)-5-(4-fluorophenyl)-3-trifluoromethylpyrazole [ No CAS ]
5-hydroxy-3-(4-fluorophenyl)-1-(4,6-dimethylpyrimidin-2-yl)-5-trifluoromethyl-Δ²-pyrazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%; 58%	In ethanol; for 7h;Reflux;	General procedure: An equimolar mixture of 2-hydrazino-4,6-dimethylpyrimidine 1(0.27 g, 2 mmol) and aryltrifluoromethyl-b-diketones 2d-h (2 mmol) was refluxed in ethanol (25 mL) for 7 h. The reaction wasmonitored by tlc. On completion of the reaction, solvent was evaporated in vacuo. The tlc and 1H NMR of the reaction mixture showed the formation of two products in the ratio given in Table 1. Column chromatography separation using silica gel (100-200 mesh) with petroleum ether : ethyl acetate (99:1) as an eluent afforded 3 and further elution of column with petroleum ether :ethyl acetate (99:2) furnished the second product 4.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 70,p. 350 - 357

71
[ 23906-13-0 ]
[ 582-65-0 ]
1-(4,6-dimethylpyrimidin-2-yl)-3-(4-fluorophenyl)-5-trifluoromethylpyrazole [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 70,p. 350 - 357

72
[ 582-65-0 ]
[ 1037590-14-9 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 60 - 66

73
[ 582-65-0 ]
7-fluoro-3-(trifluoromethyl)indeno[2,1-c]pyran-1,9-dione [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 60 - 66

74
[ 582-65-0 ]
8-Fluoro-2-(trifluoromethyl)-6H-pyrano[3,4-c]quinoline-4,5-dione [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 60 - 66
[2]Tetrahedron,2014,vol. 70,p. 60 - 66

75
4-(5-amino-3-phenyl-1H-pyrazol-1-yl)benzenesulfonamide [ No CAS ]
[ 582-65-0 ]
4-[6-(4-fluorophenyl)-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]benzenesulfonamide [ No CAS ]
N-{1-[4-(aminosulfonyl)phenyl]-3-phenyl-1H-pyrazol-5-yl}acetamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 5490 - 5503

76
[ 582-65-0 ]
[ 1427266-41-8 ]
N-[1-[4-(aminosulfonyl)phenyl]-3-(4-methylphenyl)-1H-pyrazol-5-yl]acetamide [ No CAS ]
4-[6-(4-fluorophenyl)-3-(4-methylphenyl)-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 5490 - 5503

77
[ 582-65-0 ]
[ 1427266-42-9 ]
N-[1-[4-(aminosulfonyl)phenyl]-3-(4-chlorophenyl)-1H-pyrazol-5-yl]acetamide [ No CAS ]
4-[3-(4-chlorophenyl)-6-(4-fluorophenyl)-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 5490 - 5503

78
[ 582-65-0 ]
[ 6147-53-1 ]
C₂₀H₁₀CoF₈O₄*2H₂O [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 1336 - 1347

79
[ 7357-70-2 ]
[ 582-65-0 ]
[ 625370-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 20℃;Reflux;	General procedure: Cyanothioacetamide (for X=S) (1.5 equiv) or cyanoacetamide (for X=O) (1.5 equiv) was added to a solution of the 1, 3-diones (for R4= -CF3 and -CH3) (1.0 equiv) or enaminones (for R4=H) (1.0 equiv) in ethanol in the presence of DABCO (1.0 equiv) at room temperature. The reaction mixture was stirred under reux for 3-6 h until complete conversion of the starting materials, as monitored by TLC. After cooled to room temperature, the solvent was evaporated under reduced pressure and the residue was neutralized with diluted hydrochloric acid (1 N) to precipitate the crude products. After filtrated and dried in vacuo, the product can be straight used for step d. Yield: 70-90%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1581 - 1588

80
[ 582-65-0 ]
[ 107-91-5 ]
6-(4-fluoro-phenyl)-2-oxo-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 20℃;Reflux;	General procedure: Cyanothioacetamide (for X=S) (1.5 equiv) or cyanoacetamide (for X=O) (1.5 equiv) was added to a solution of the 1, 3-diones (for R4= -CF3 and -CH3) (1.0 equiv) or enaminones (for R4=H) (1.0 equiv) in ethanol in the presence of DABCO (1.0 equiv) at room temperature. The reaction mixture was stirred under reux for 3-6 h until complete conversion of the starting materials, as monitored by TLC. After cooled to room temperature, the solvent was evaporated under reduced pressure and the residue was neutralized with diluted hydrochloric acid (1 N) to precipitate the crude products. After filtrated and dried in vacuo, the product can be straight used for step d. Yield: 70-90%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1581 - 1588

81
[ 582-65-0 ]
[ 1581726-12-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1581 - 1588

82
[ 582-65-0 ]
[ 1260243-04-6 ]
[ 333761-24-3 ]

Yield	Reaction Conditions	Operation in experiment
76.63%	With acetic acid; at 115℃; for 7h;	Amino-1H-pyrazole-4-carboxylate obtained in the step 1) (15.58, 0.1 mmol) and the 1-p-fluorophenyl-4,4,4-tris Fluorobutanedione (23.4 g, 0.1 mol) was placed in a vessel;The mixture E was dissolved in 50 mL of glacial acetic acid to give a mixture E which was heated to 115 C under heating. The mixture was heated to reflux for 7 hours, cooled and allowed to stand, precipitating a yellow-green needlepoint Solid; the solid is filtered, washed, dried,Ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5- a] pyrimidine-3-carboxylate;The mass of the obtained product ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05 g. Yield: 76.63%.
76.63%	With acetic acid; at 115℃; for 7h;	A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate obtained in the step 1) (15.5 g, 0.01 mol) and 1-p-fluorophenyl-4,4,4 , -trifluorobutanedione (23.4 g, 0.1 mol) was placed in a vessel; 3.2) Dissolve the mixture in a container with 50 ml of glacial acetic acid to give a mixture E, placing the container on an electric heating barHeating to 115 C;3.3) The mixture E was heated to reflux for 7 hours, cooled, allowed to stand, and precipitated as a yellow-green needle-like solid;Ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5-a] pyrimidine-3-carboxylate was obtained after filtration, washing and drying;The process used in the process is cold glacial acetic acid.The mass of the product ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5_a] pyrimidine-3-carboxylate obtained in 27.05 g. Yield: 76.63%.
76.63%	With acetic acid; for 7h;Reflux;	Ethyl 5-amino-1H-pyrazole-4-carboxylate (15.5 g, 0.1 mol) obtained in step 1) And 1-p-fluorophenyl-4,4,4-trifluorobutanedione (23.4 g, 0.1 mol) obtained in step 2) were placed in a vessel; The mixture in the container was dissolved using 50 mL of glacial acetic acid to give a mixture E, the vessel was placed under an electrothermal condition and heated to 115 C; The mixture E was heated to reflux, and after 7 hours, the mixture was allowed to stand for cooling to remove the yellow-green needle-like solid; the solid was filtered, washed and dried, To give ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate; and the article used for the washing process is cold glacial acetic acid. The resulting product The mass of ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05 g. Yield: 76.63%.

76.63%	With acetic acid; at 115℃; for 7h;	3.1) Ethyl 5-amino-1H-pyrazole-4-carboxylate (15.5 g, 0.1 mol) obtained in step 1)And p-fluorophenyl-4,4,4-trifluorobutanedione (23.4 g, 0.1 mol) obtained in step 2) were placed in a vessel;3.2) After dissolving the mixture in the vessel with 50 mL of glacial acetic acid,To obtain a mixture E,The container was placed under an electric heating condition,Heating up to 115C ;3.3) The mixture E was heated to reflux,After 7 hours,Cooling, standing, precipitation of yellow - green needle - like solid;The solid was filtered, washed, dried,To give ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate;The article used for the washing process is cold glacial acetic acid.The mass of the obtained product 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05 g.Yield: 76.63%.
76.63%	With acetic acid; at 115℃; for 7h;	3.1) To a solution of ethyl 5-amino-1H-pyrazole-4-carboxylate (15.5 g, 0.1 mol) obtained in step 1) and 1-p-fluorophenyl-4,4,4 , - trifluorobutanedione (23.4 g, 0.1 mol) was placed in a vessel;3.2) The mixture in the container was dissolved using 50 mL of glacial acetic acid to give the mixture E, the vessel was placed under an electrothermal condition and heated to 115 C;3.3) The mixture E was heated to reflux and after 7 hours,Cooling, standing,The solid was filtered, washed and dried to give 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylic acid B ester;The article used for the washing process is cold glacial acetic acid.The mass of the obtained product 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05 g. Yield: 76.63%.
76.63%	With acetic acid; at 115℃; for 7h;	3) Synthesis of ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3.1) The ethyl 5-amino-1H-pyrazole-4-carboxylate obtained in step 1) (15.5 g, 0.1 mol) and step 2)The obtained 1-p-fluorophenyl-4,4,4-trifluorobutanedione (23.4 g, 0.1 mol) was placed in a container;3.2) After dissolving the mixture in the vessel with 50 mL of glacial acetic acid, a mixture E1 is obtained,The container is placed under electric heating conditions, heated to 115 ;3.3) The mixture E1 was heated to reflux, after 7 hours, cooled and allowed to stand, yellow-green needle-like solid precipitated; the solidAfter filtration, washing and drying, ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was obtained; For cold glacial acetic acid.The product obtained5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-The quality of ethyl carboxylate is27.05g.Yield: 76.63%.
76.63%	With acetic acid; at 115℃; for 7h;	3.1) Ethyl 5-amino-1H-pyrazole-4-carboxylate obtained in step 1) (15.5 g, 0.1 mol) and 1-p-fluorophenyl-4,4,4 , Trifluorobuten dione (23.4 g, 0.1 mo 1) was placed in a container;3.2) using 50mL glacial acetic acid to dissolve the mixture in the container, to obtain a mixture E, the container is placed under electric heating conditions, warmed to 115 C; 3.3) The mixture E was heated to reflux, after 7 hours, cooled, allowed to stand, precipitated yellow-green needle-like solid; solid overAfter filtration, washing and drying, ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was obtained; For cold glacial acetic acid. The resulting product, ethyl 5- (4-fluorophenyl) -7_trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05g. Yield: 76.63%
	With acetic acid; for 6h;Reflux;	A solution of ethyl 5-amino-1H-pyrazole-4-carboxylate (15.5 g, 0.1 mol) and 4,4-trifluoro-1-(4-fluorophenyl)-butane-1,3-dione (23.4 g, 0.1 mol) in acetic acid (50 mL) was heated at reflux for 6 h. After cooling to room temperature, the formed precipitate was filtered off, washed with water, and dried. The resulting ethyl carboxylate was added to a mixture of NaOH (5.6 g, 0.14 mol) in EtOH/water (1 : 3) (120 mL), and the reaction mixture was kept at 65 C for 5 h. The mixture was cooled to room temperature and acidified with concentrated HCl until pH 1 was reached. The formed precipitate was filtered off, washed with water, and recrystallised from MeCN to give 20.6 g pure 5-(4-fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid in 63.4% yield
	With acetic acid; for 6h;Reflux;	A solution of ethyl 5-amino-1H-pyrazole-4-carboxylate (1) (15.5 g,0.1 mol) and 4,4,4-trifluoro-1-(4-fluorophenyl)butane-1,3-dione(23.4 g, 0.1 mol) in acetic acid (50 mL) was heated at reflux for 6 h.After cooling to room temperature, the formed precipitate 3 wasfiltered off, washed with water and dried: m.p. 167-169 C; IR (KBr,cm-1): 2965, 1697, 1634, 1594, 1570, 1466, 1397, 1327, 1198, 1171,1027, 848, 778; 1H NMR (600 MHz, DMSO-d6): delta 8.75(s, 1H, ArH),8.48 (m, 2H, ArH), 8.37 (s, 1H, ArH), 7.45 (m, 2H, ArH), 4.34 (q,J = 7.2 Hz, 2H, CH2), 1.36 (t, J = 7.2 Hz, 3H, CH3).The resulting ethyl carboxylate 3 was added to a mixture of NaOH(5.6 g, 0.14 mol) in EtOH/water (1:3) (120 mL) and the reactionmixture was kept at 65 C for 5 h. The mixture was cooled to roomtemperature and acidified with concentrated HCl until pH 1 wasreached. The formed precipitate was filtered off, washed with water, and recrystallised from MeCN to give: 20.6 g pure 5-(4-fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (4) in 63.4% yield (two steps);

Reference： [1]Patent: CN105884783,2016,A .Location in patent: Paragraph 0062; 0063; 0064; 0065; 0066
[2]Patent: ,2016, .Location in patent: Paragraph 0045;0048
[3]Patent: CN105949202,2016,A .Location in patent: Paragraph 0062-0066
[4]Patent: CN106008517,2016,A .Location in patent: Paragraph 0062; 0063; 0064; 0065
[5]Patent: CN106008519,2016,A .Location in patent: Paragraph 0062; 0063; 0064; 0065; 0066
[6]Patent: CN105949200,2016,A .Location in patent: Page/Page column 7; 23
[7]Patent: CN105949201,2016,A .Location in patent: Paragraph 0062-0066
[8]Journal of Chemical Research,2015,vol. 39,p. 4 - 6
[9]Journal of Chemical Research,2016,vol. 40,p. 107 - 109

83
[ 582-65-0 ]
diethyl-2-[5-(4-fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamido]pentanedioate [ No CAS ]

Reference： [1]Journal of Chemical Research,2015,vol. 39,p. 4 - 6

84
[ 582-65-0 ]
(Z)-2-ethoxycarbonyl-3-(4-fluorophenyl)-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)acrylic acid [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 8863 - 8871

85
[ 582-65-0 ]
[ 1348742-51-7 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 8863 - 8871
[2]Tetrahedron,2014,vol. 70,p. 8863 - 8871

86
[ 582-65-0 ]
sodium (E)-2-ethoxycarbonyl-3-(4-fluorophenyl)-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)acrylate [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 8863 - 8871

87
[ 582-65-0 ]
(4-fluorophenyl)(5-trifluoromethyl-1,2,3-triazol-4-yl)methylenemalonic acid [ No CAS ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 8863 - 8871
[2]Tetrahedron,2014,vol. 70,p. 8863 - 8871

88
[ 582-65-0 ]
2-fluoro-1-(4-fluorophenyl)-2-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1277 - 1282

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	582-65-0	MDL No. :	MFCD03419766
Formula :	C₁₀H₆F₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KEZLARPKXOHKJS-UHFFFAOYSA-N
M.W :	234.15	Pubchem ID :	2771476
Synonyms :

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	4
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.6
TPSA :	34.14 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.83 cm/s

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	2.68
Log Po/w (WLOGP) :	4.21
Log Po/w (MLOGP) :	2.23
Log Po/w (SILICOS-IT) :	3.42
Consensus Log Po/w :	2.78

[ CAS No. 582-65-0 ] {[proInfo.proName]}

Quality Control of [ 582-65-0 ]

Related Doc. of [ 582-65-0 ]

Product Details of [ 582-65-0 ]

Calculated chemistry of [ 582-65-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 582-65-0 ]

Application In Synthesis of [ 582-65-0 ]

[ 582-65-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.99
Solubility :	0.238 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-3.05
Solubility :	0.209 mg/ml ; 0.000893 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0314 mg/ml ; 0.000134 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed