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CAS No. : | 175711-83-8 | MDL No. : | MFCD04116328 |
Formula : | C8H6ClFO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OIGMDNONQJGUCF-UHFFFAOYSA-N |
M.W : | 172.58 | Pubchem ID : | 15030552 |
Synonyms : |
|
Chemical Name : | 4'-Chloro-2'-fluoroacetophenone |
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.6 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 1.76 |
Log Po/w (XLOGP3) : | 2.33 |
Log Po/w (WLOGP) : | 3.1 |
Log Po/w (MLOGP) : | 2.79 |
Log Po/w (SILICOS-IT) : | 3.21 |
Consensus Log Po/w : | 2.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.72 |
Solubility : | 0.332 mg/ml ; 0.00193 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.33 |
Solubility : | 0.812 mg/ml ; 0.0047 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.041 mg/ml ; 0.000238 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; dichloromethane; at 0 - 20℃; for 2h; | Reference Example 8 : 1- (4-chloro-2-fluorophenyl) ethanone To a solution 4-chloro-2-fluorobenzoic acid (leq) in CH2C12 (1.6 M) was added N, O-dimethylhydroxylamine hydrochloride (1. 5 eq), EDCI (1.5 eq) and triethylamine (4 eq). The reaction mixture was stirred at rt for 16 hrs, concentrated and 0. 5M aqueous citric acid was added. The mixture was extracted with 1: 1 EtOAc: Et20. The combined organic layers were washed with brine, dried over MgS04 and concentrated to give 4-chloro-2-fluoro-N-methoxy-N- methylbenzamide, which was used as such for the next step. To a solution of the above benzamide (leq) in CHsClz (0.5 M) at 0C was added 3M/EtzO MeMgBr (1.25 eq). The reaction mixture was slowly warmed to rt over a 2 hrs period, quenched with 0.5 M aqueous citric acid and extracted with Et20. The combined organic layers were washed with brine, dried over MgS04 and concentrated. The residue was purified by flash chromatography on silica gel eluted with 20% EtOAc/hexane to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(3) Anhydrous magnesium chloride (6.7g, 70mmol) and triethylamine (24.2g, 0.24mol) were added to toluene (120ml), and dimethyl malonate (15.8g, 0.12mmol) was added dropwise under cooling with water. After the reaction mixture was stirred at room temperature for 3 hours, a toluene solution of the compound prepared in reference example 6-(2) (about 20g) in toluene (20ml) was added dropwise at about 20 ØC. The resulting mixture was stirred for 14 hours at room temperature. After concentrated hydrochloric acid (20ml) was added to the reaction mixture under cooling with ice, the resulting mixture was added to ice water. The organic layer was separated, and the aqueous layer was further extracted with toluene. The toluene layer was combined with the former organic layer, washed with brine, dried, and then evaporated to give an oil. The oil was added to a mixture of DMSO (80ml) and water (4ml). The mixture was gradually heated, stirred at 140 ØC (the temperature of oil bath) for 2 hours, and further stirred at 180 ØC for 1 hour. After cooling, the reaction mixture was poured into ice water, and extracted with diethyl ether. The extract was washed with brine, dried, and then evaporated. The residue was distilled under reduced pressure to give 4-chloro-2-fluoroacetophenone (14.4g, oil). 1H-NMR(CDCl3) delta 2.63(3H, d, J=5.03Hz), 7.12-7.25(2H, m), 7.84(1H, t, J=9.02Hz). b.p.:100-104 ØC/20mmHg |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 4-(dimethylamino)pyridine tribromide; In acetic acid; at 20℃; for 24h; | A mixture of <strong>[175711-83-8]4'-chloro-2'-fluoroacetophenone</strong> (17.5 g, 100 mmol), 4-(dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mL) was stirred at room temperature for 24 h. Water (150 mL) was added and after stirring for 30 min the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%). |
95% | With 4-dimethylaminopyridine tribromide; acetic acid; at 20℃; for 24h; | A mixture of 4?-chloro-2?-fluoroacetophenone (17.5 g, 100 mmol), 4- (dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mL) was stirred room temperature for 24 h. Water (150 mL) was added and after stirring for 30 mm the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%). |
95% | With 4-(dimethylamino)pyridine tribromide; acetic acid; at 20℃; for 24h; | A mixture of 4?-chloro-2?-fluoroacetophenone (17.5 g, 100 mmol), 4-(dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mE) was stirred at room temperature for 24 h. Water (150 mE) was added and after stirring for 30 mm the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%). |
85.8% | With pyridinium hydrobromide perbromide; In tetrahydrofuran; at 25℃; for 2h;Green chemistry; | As shown in Figure 2, Tetrahydrofuran (400 mL) and <strong>[175711-83-8]2-fluoro-4-chloroacetophenone</strong> (74.2 g, 1.0 eq) were added to the reaction flask at room temperature, stirred and dissolved completely, and the temperature was controlled at 25 C. A solution of pyridinium tribromide (137.5 g, 1.0 eq) in tetrahydrofuran was added dropwise. The reaction system was stirred at 25 C for 2 hours. after filtration, the filter cake was rinsed with a small amount of tetrahydrofuran to give a yellow solid, dried.Recrystallization from n-hexane (900 ml) and ethyl acetate (100 ml). 92.8 g of yellow was obtained in a yield of 85.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sulfuryl dichloride; In methanol; n-heptane; at 0℃; for 3.5h;Inert atmosphere;Product distribution / selectivity; | PREPARATION 2 2-Chloro-<strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethanone</strong> In a 1 L round bottom flask combine <strong>[175711-83-8]4'-chloro-2'-fluoroacetophenone</strong> (40 g, 231.8 mmol), heptane (120 mL), and methanol (16 mL). Cool to 0 C. and place under nitrogen. Dissolve sulfuryl chloride (21.5 mL, 1.15 equiv.) in heptane (120 mL) and charge to an addition funnel Add drop-wise to the reaction over 60 min. Stir for 2.5 h at 0 C.; a white precipitate forms during this time. Charge the addition funnel with 1 M sodium bicarbonate (400 mL) then add to the reaction drop-wise. After all gas evolution stops, filter the biphasic suspension to collect the title compound (38.18 g, 80%) as white needles. 1H NMR (DMSO-d6) delta 5.00 (d, 2H, J=2.5 Hz), 7.43 (m, 1H), 7.63 (m, 1H), 7.89 (t, 1H, J=8.4 Hz). |
57% | With sulfuryl dichloride; In methanol; dichloromethane; at 0 - 20℃; for 24h;Inert atmosphere; | Intermediate P6: 2-Chloro- 1 -(4-chloro-2-fluorophenyl)ethanone To the mixture of 1 -(4-chloro-2-fluorophenyl)ethanone (4.00 g, 23.2 mmol), dichloromethane (12 mL) and methanol (1 .6 mL) cooled to 0 C under argon atmosphere sulfuryl chloride (2.35 mL, 29.0 mmol) solution in dichloromethane (5 mL) was added during 10 minutes. The reaction mixture was stirred for 24 hours at room temperature. Then, the reaction mixture was cooled to 0 C and 14% aqueous solution of sodium hydroxide (20 mL) was added. The mixture was extracted with dichloromethane (2 chi 20 mL). Organic layers were combined, washed with brine, dried (Na2S04) and evaporated under reduced pressure. Remaining solid was dissolved in boiling ethyl acetate and heptane was added to crystallize crystals. White crystals were filtered and washed with heptane to obtain title product with the yield of 57% (2.74 g, 13.2 mmol). 1 H NMR (500 MHz, CDCl3) delta 7.93 (t, J=8.1 Hz, 1 H), 7.29 (dd, J=9.0 Hz, 1 .2 Hz, 1 H), 7.23 (dd, J=10.8 Hz, 1 .9 Hz, 1 H), 4.70 (d, J=2.9 Hz, 2H ). 13C NMR ( 125 MHz, CDCl3) delta 188. 1 , 162.6, 141 ,5, 132.2 (d, J=3.7 Hz), 125.6 (d, J=3.2 Hz), 121 .1 , 1 17.3 (d, J=27.2 Hz), 49.8 (d, J=1 1 .5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; for 5h; | j00392j To a solution of 1-(4-chloro-2-fluoro-phenyl)ethanone (7.0 g, 4lmmol) and potassium carbonate (11 g, 81 mmol) in dimethyl formamide (50 mL) at 25 C was added methyl thioglycolate (7.3 g, 69 mmol). The mixture was stirred for 5 hours, then diluted with water (50 mL) and extracted with ethyl acetate (3 x 40 mL). The combined organic phases were concentrated in vauo to give compound B-60(8 g, crude) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20℃; for 18h; | a) To a solution of 4'-chloro-2'-fluoroacetopheiioiie (7.5 g, 43.6 mmol) and (?)-(-)- 1- butanesulfinamide (5.3 g, 44.0 mmol) in anhydrous tetrahydrofuran (THF, 125 mL) was added titanium(IV) ethoxide (Ti(OEt)4, 24.8 g, 109.0 mmol). The reaction mixture was stirred at room temperature for 18 h. The mixture was poured into a solution of brine, and the mixture was stirred at room temperature for 1 h. The solution was filtered, and the phases were separated. The organic layer was further washed with brine. The organic layer was then dried with anhydrous sodium sulfate (Na2S04), filtered, and concentrated in vacuo. The crude material was used without further purification (7.9 g, 28.7 mmol, 66%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.2.4 Synthesis of 4-(((5-(4-chloro-2-fluorophenyl)isoxazol-3-yl)methyl)amino)-A - hydroxytetrahydro-2H-thiopyran-4-carboxamide 1 ,1 -dioxide [1.2.4] Step 1. Synthesis of ethyl 4-(4-chloro-2-fluorophenyl)-2,4-dioxobutanoate. [1.2.4a] 1.2.4a To a solution of LHMDS (1 .0 M in THF, 37.7 mL, 37.7 mmol) in ether (45 mL) at -78 C was added a solution of 1 -(4-chloro-2-fluorophenyl)ethanone (5.0 g, 29 mmol, 1 equiv) in ether (15 mL). After stirring at -78 C for 30 min, diethyl oxalate was added, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated aqueous NH4CI solution. The precipitate was collected by filtration and azeotroped with toluene to afford ethyl 4-(4-chloro-2-fluorophenyl)-2,4-dioxobutanoate which was used in the next step without further purification. MS m/z 273.1 [M+H]+. | ||
General procedure: To a stirred solution of acetophenone (27b) (2.0 g, 16.5 mmol)inMTBE (30 mL) was added lithium hexamethyldisilazide (1.3M, 12.7 mL, 16.5 mmol) dropwise at 0 C;After addition, the reaction mixture was stirred at 0 C for 0.5 h and diethyl oxalate (3.0 g, 20.8 mmol) wasadded dropwise. Then, the mixture was stirred at room temperature overnight. TLC analysis showedreaction was complete and the reaction mixture was extracted with H2O (20 mL). The aqueous layerwas separated, acidified by hydrochloric acid (1M) to pH6 and extracted by ethyl acetate (10 mL 2).The combined organic layer was concentrated in vacuum to give 28b as yellow oil, which was used fornext step without further purification (3.4 g, 92.7% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74%; 3% | With 18-crown-6 ether; potassium carbonate; In toluene; at 70℃; for 20h; | The mixture of 4?-chloro-2?-fluoroacetophenone (3.97 mL, 29.0 mmol), diethyl cyanomethylphosphonate (5.16 mL, 31.9 mmol), 18-crown-6 (117 mg, 0.435 mmol), potassiumcarbonate (6.01 g, 43.5 mmol) and toluene (80 mL) was heated to 70 C for 20 hours. Reaction mixture was cooled and water (100 mL) was added. Phases were separated and aqueous phase was extracted with AcOEt (4 x 100 mL). Organic phases were combined, washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography (silicagel, eluent: heptane 100% toheptane:AcOEt = 98:2, v/v). (E)-3-(4-Chloro-2-fluorophenyl)but-2-enenitrile as white crystals and (Z)-3-(4-chloro-2-fluorophenyl)but-2-enenitrile as a light yellow oil were obtained with the yields of 74% (4.20 g, 21.5 mmol) and 3% (156 mg, 0,80 mmol), respectively. Also the mixture of isomers (E) and (Z) as a colorless oil was obtained with a yield of 22% (1.23 g, 6.28 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 80℃; for 41h; | [000408] To a mixture of Compound 43A (25 g, 0.145 mol) and K2C03 (26 g, 0.188 mol) in dry DMF (150 mL) at 0 C was added ethyl 2-mercaptoacetate (16 mL, 0.146 mmol) in small portions over 1 h. The mixture was slowly warmed to room temperature and stirred for 16 h. The reaction mixture was heated at 80 C for 24 h. After it was cooled, to it was added water (300 mL). The resulting mixture was stirred at room temperature for 30 mm. and filtered. The filtrate was diluted with ethyl acetate (200 mL), washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, concentrated, and offer the Compound 43B. LC-MS (ESI) mlz: 255 [M+H] 1H-NMR (CDC13, 400 MHz): c (ppm) 1.41 (t, J 7.6 Hz, 3H), 2.74 (s, 3H), 4.39 (q, J = 6.8 Hz, 2H), 7.35-7.38 (m, 1H), 7.72 (d, J 8.4 Hz, 1H), 7.78 (d, J- 1.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tert.-butylhydroperoxide; BOC-glycine; iodine; In toluene; at 20 - 60℃; for 15h;Schlenk technique; Inert atmosphere; | General procedure: To a Schlenk tube equipped with a stirred bar a solution of sulfonylhydrazines 1 (0.2 mmol), ketones 2 (0.3 mmol), indoles 3 (0.3 mmol) in toluene (1.0 mL) was added under argon atmosphere at room temperature, followed by adding I2 (20 mol%), TBHP (2.0 equiv) and N-Boc glycine (20 mol%). The reaction mixture was then stirred at 60 C for 15 h. The mixture was concentrated in vacuo to yield the crude product, which was purified by flash chromatography on silica gel (eluent:petroleum ether (PE)/EtOAc, 25:1) to provide the desired [2,3]-fused indolines 4 and 5 as white solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (+)-B-chlorodiisopinocamphenylborane; In tetrahydrofuran; hexane; at -78 - -25℃; for 7h;Inert atmosphere; | 107621 To a solution of <strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethan-1-one</strong> (10 g, 58 mmol) in tetrahydrofuran (100 mL) at -78 C under a nitrogen atmosphere was added (+)-B20 Chlorodiisopinocampheylborane (50 to 60% wt in hexanes, 9.2 mL, 64 mmol), slowly. The resultingmixture was slowly warmed to -25 C and stirred at this temperature for 2 h. 1-(4-Chloro-2- fluorophenyl)ethan-1-one was detected by LCMS (?liquid chromatography mass spectrometry?) and HPLC, and the mixture was cooled back to -78 C. Additional (+)-BChlorodiisopinocampheylborane (50 to 65% wt in hexanes, 5.4 mL, 38 mmol) was added to themixture at -78 C. The resulting mixture was slowly warmed to -25 C and stirred at this temperature for 5 h. Diethanolamine (18 mL, 191 mmol) was added to the reaction mixture, which was then stirred at room temperature for 3 d. The reaction was filtered, and the filtrate was concentrated and purified by silica gel chromatography (0 to 30% ethyl acetate in hexanes) to afford 18.8 g impure (R)- 1 -(chloro-2-fluorophenyl)ethan- 1 -ol. | |
18.8 g | To a solution of <strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethan-1-one</strong> (10 g, 58 mmol) in THF (100 mL) at -78 C. under a nitrogen atmosphere was added (+)-DIP-Cl (50 to 60% wt in hexanes, 9.2 mL, 64 mmol), slowly. The resulting mixture was slowly warmed to -25 C. and stirred at this temperature for 2 h. 1-(4-Chloro-2-fluorophenyl)ethan-1-one was detected by LCMS and HPLC, and the mixture was cooled back to -78 C. Additional (+)-DIP-Cl (50 to 65% wt in hexanes, 5.4 mL, 38 mmol) was added to the mixture at -78 C. The resulting mixture was slowly warmed to -25 C. and stirred at this temperature for 5 h. Diethanolamine (18 mL, 191 mmol) was added to the reaction mixture, which was then stirred at room temperature for 3 d. The reaction was filtered, and the filtrate was concentrated and purified by silica gel chromatography (0 to 30% ethyl acetate in hexanes) to afford 18.8 g impure (R)-1-(chloro-2-fluorophenyl)ethan-1-ol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.2 g | With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h; | To a solution of <strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethan-1-one</strong> (25 g, 145 mmol) in MeOH (300 mL) at 0 C. was added NaBH4 (8.0 g, 220 mmol) portion-wise. Then, the mixture was slowly warmed to room temperature and stirred for 1 h. The reaction was diluted with EtOAc and sat. sodium bicarbonate solution. The organic phase was separated, and the aqueous layer was extracted with EtOAc (2*). The combined organics were dried over sodium sulfate and concentrated to afford the crude product, which was purified by silica gel chromatography to afford 1-(4-chloro-2-fluorophenyl)ethan-1-ol (24.2 g). This material was dissolved in DCM (600 mL), and the solution was charged with triphenylphosphine (278 mmol, 72.9 g) and CCl4 (556 mmol). The mixture was stirred for 3 d at room temperature. The mixture was concentrated to about 50 mL, and the mixture was filtered through a silica gel plug. The solution was concentrated, and the residue was suspended in DCM:hexanes 1:2 and stirred for 20 min. The material was filtered, and the residue was suspended in hexanes and filtered. The residue was purified by silica gel chromatography, eluting with hexanes, to afford 4-chloro-1-(1-chloroethyl)-2-fluorobenzene (24 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 24h; | Into a 100-mL round-bottom flask, was placed <strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethan-1-one</strong> (10 g,57.94 mmol, 1.00 equiv) and 1,3-diethyl 2-oxopropanedioate (15 mL). The resulting solutionwas stirred for 24 hours at 130C. The resulting mixture was concentrated under vacuum. This resulted in 24 g (crude) of 1 ,3-diethyl 2-[2-(4-chloro-2-fluorophenyl)-2-oxoethyl]-2- hydroxypropanedioate as a black oil which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.7% | With diethylamine; zinc(II) chloride; In toluene; tert-butyl alcohol; at 35℃; for 24h;Green chemistry; | As shown in Figure 3, Zinc chloride (68.1 g, 2.5 eq) and toluene (180 ml) were added to the reaction flask at room temperature and stirring was started. the temperature control below 35 C, Diethylamine (19.3 g, 2 eq) was added dropwise, tert-butanol (30 ml) was added, and the reaction was stirred for 2 hours, and the temperature was controlled below 35 C. 2-Fluoro-4-chloroacetophenone (34.5 g, 1.0 eq) and 1-(4-chloro-2-fluorophenyl)-2-bromoethanone (60.4 g, 1.2 eq) in toluene (100 mL) The reaction was stirred for 24 hours. The reaction was quenched with 2M aqueous HCl (350 mL).Stir for 2 hours, filter, the solid was rinsed with toluene (100 ml) and dried under vacuum at 45 C. 63.6 g of an off-white solid product was obtained in a yield of 92.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper (II) nitrate tetrahydrate; oxygen; In acetonitrile; at 180℃; under 18751.9 Torr; for 1.5h;Green chemistry; | <strong>[175711-83-8]2-fluoro-4-chloroacetophenone</strong> 25g (144.9mmol, 1.0eq), Cu(NO3)2·4H2O 7.0g (29.0mmol, 0.2eq), acetonitrile 250mL (10V),The temperature of the outer bath of the reaction coil was raised to 180 C, and the coil pressure was adjusted to 2.5 MPa with oxygen to start the charging. The residence time of the system was 1.5 h and the oxygen was 3 to 5 eq.The system was directly pumped into 375 mL of purified water, and the pH of the system was adjusted to 12-14 with NaOH solids.The aqueous phase was extracted twice with 125 mL MTBE, and the aqueous phase was adjusted to pH 1 with concentrated HCl.A large amount of solid was precipitated, and 19.3 g of the target product was obtained by filtration, yield 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With toluene-4-sulfonic acid; In toluene; at 140℃; for 60h;Dean-Stark; | To a solution of 3-bromobenzene-1,2-diol (330 g, 1.75 mol) in toluene (1.5 L) were added <strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethanone</strong> (316 g, 1.83 mol) and p-toluenesulfonic acid (6.02 g, 35.0 mmol). The reaction apparatus was fitted with a Dean-Stark trap, and the reaction mixture was heated at 140 C. for 60 hours, whereupon the solution was concentrated in vacuo and purified using silica gel chromatography (Eluent: petroleum ether); C4 was obtained as a mixture of yellow oil and solid. Yield: 158 g, 460 mmol, 26%. 1H NMR (400 MHz, chloroform-d): delta 7.54 (dd, J=8.4, 8.4 Hz, 1H), 7.17-7.10 (m, 2H), 6.95 (dd, J=7.9, 1.4 Hz, 1H), 6.75 (dd, component of ABX pattern, J=7.8, 1.4 Hz, 1H), 6.70 (dd, component of ABX pattern, J=7.9, 7.9 Hz, 1H), 2.11 (d, J=1.1 Hz, 3H). |
Tags: 175711-83-8 synthesis path| 175711-83-8 SDS| 175711-83-8 COA| 175711-83-8 purity| 175711-83-8 application| 175711-83-8 NMR| 175711-83-8 COA| 175711-83-8 structure
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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. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
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. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
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 |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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