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Chemical Structure| 454464-38-1 Chemical Structure| 454464-38-1

Structure of 454464-38-1

Chemical Structure| 454464-38-1

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Product Details of [ 454464-38-1 ]

CAS No. :454464-38-1
Formula : C14H10ClF3
M.W : 270.68
SMILES Code : FC(C1=CC=C(C2=CC=C(CCl)C=C2)C=C1)(F)F
MDL No. :MFCD16251113

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Application In Synthesis of [ 454464-38-1 ]

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

  • Downstream synthetic route of [ 454464-38-1 ]

[ 454464-38-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 457889-46-2 ]
  • [ 454464-38-1 ]
YieldReaction ConditionsOperation in experiment
98% With thionyl chloride; In chloroform; at 20℃; for 12h; Example 23A 4-Chloromethyl-4'-trifluoromethylbiphenyl A solution of 5.0 g (19.82 mmol) of (4'-trifluoromethylbiphenyl-4-yl)methanol from Example 22A in 40 ml of chloroform is mixed with 2.89 ml (39.65 mmol) of thionyl chloride dissolved in 10 ml of chloroform, and the mixture is stirred at room temperature for 12 hours. After reaction is complete, the reaction mixture is concentrated to dryness, and the residue is taken up ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is subsequently separated off, dried over sodium sulfate and concentrated after filtration. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.43 mmol, 98% yield) of a colorless solid are obtained. 1H-NMR (300 MHz, DMSO-d6, delta/ppm): 7.91 (2H, d), 7.82 (2H, d), 7.78 (2H, d), 7.58 (2H, d), 4.83 (2H, s). MS (EI): 270 (M+).
98% With thionyl chloride; In chloroform; at 20℃; for 12h; Example 11A 4-Chloromethyl-4'-trifluoromethylbiphenyl A solution of 5.00 g (19.8 mmol) of (4'-trifluoromethylbiphenyl-4-yl)methanol in 40 ml of chloroform is mixed with 2.89 ml (39.7 mmol) of thionyl chloride dissolved in 10 ml of chloroform, and the mixture is stirred at room temperature over 12 hours. After reaction is complete, the reaction mixture is concentrated to dryness, and the residue is taken up ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is subsequently separated off, dried over sodium sulfate and concentrated after filtration. The resulting crude product is purified by flash chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.4 mmol, 98% of theory) of the title compound are obtained. 1H-NMR (300 MHz, DMSO-d6, delta/ppm): 4.83 (s, 2H), 7.58 (d, 2H), 7.78 (d, 2H), 7.91 (d, 2H), 7.82 (d, 2H). MS (E1): 270 (M+).
98% With thionyl chloride; In chloroform; at 20℃; for 12h; Example 16A; 4-Chloromethyl-4'-trifluoromethylbiphenyl 2.89 ml (39.65 mmol) of thionyl chloride dissolved in 10 ml of chloroform are added to a solution of 5.0 g (19.82 mmol) of (4'-trifluoromethylbiphenyl-4-yl)methanol in 40 ml of chloroform, and the mixture is stirred at room temperature for 12 hours. After reaction is complete, the reaction mixture is evaporated to dryness, and the residue is taken up in ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is separated off, dried over sodium sulphate and evaporated after filtration. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.43 mmol, 98% yield) of a colourless solid are obtained.1H-NMR (300 MHz, DMSO-d6, delta/ppm): 7.91 (2H, d), 7.82 (2H, d), 7.78 (2H, d), 7.58 (2H, d), 4.83 (2H, s).MS (EI): m/z=270 (M+).
98% With thionyl chloride; In chloroform; at 20℃; A solution of 5.0 g (19.82 mmol) of (4'-trifluoromethylbiphenyl-4-yl)methanol in 40 ml of chloroform is mixed with 2.89 ml (39.65 mmol) of thionyl chloride dissolved in 10 ml of chloroform, and the mixture is stirred at room temperature for 12 hours. After reaction is complete, the reaction mixture is concentrated to dryness, and the residue is taken up ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is subsequently separated off, dried over sodium sulfate and concentrated after filtration. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.43 mmol, 98% of theory) of a colorless solid are obtained.1H-NMR (300 MHz, DMSO-d6, delta/ppm): 7.91 (2H, d), 7.82 (2H, d), 7.78 (2H, d), 7.58 (2H, d), 4.83 (2H, s).MS (EI): 270 (M+).
93% With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 12h;Inert atmosphere; To a solution of [(4?-(trifluoromethyl)-[1,1?-biphenyl]-4-yl)methanol (4a, 553 mg, 2.19 mmol) in anhydrous CH2Cl2 (20 mL) were added SOCl2 (391 mg, 3.29 mmol) and DMF (32.1 mg, 0.44 mmol) at 0 C. The reaction mixture was then allowed to warm to room tempreature. After stirring the reaction mixture at room temperature for 12 h, the reaction mixture was diluted with water and extracted with ethyl acetate for 3 times. The combined organic layer was dired over MgSO4, filtered, and concentrated. The obtained residue was purified by MPLC using hexane/ethyl acetate as the eluant to give the desired product 5 as a white solid (553 mg, 93%). 1H NMR (400 MHz, CDCl3) delta7.71-7.66 (m, 4H), 7.58 (d, 2H, J=8.2 Hz), 7.50 (d, 2H, J=8.2 Hz),4.55 (s, 2H).
91% With thionyl chloride; In chloroform; at 20℃; for 12h; Compound 20' (1 eq, 9.51 mmol) was dissolved in 20 mL of CHC13. SOCl2 (2 eq, 19.0 mmol) was then added and the reaction was stirred at rt during 12h.The reaction mixture was evaporated to dryness and diluted with water (30 mL) and EtOAc (40 mL). The mixture was then extracted three times (3 x 20 mL). The combined organic phases were washed with saturated Na2C03, dried and filtered. After removal of the solvent under reduced pressure, the remaining oil was purified using column chromatography (silica gel, 98/2 Hex/EtOAc) to obtain the desired compound (Rf = 0.2) as an off white solid (2.35 g, 91%) 1H-NMR (CDC13, 600 MHz) delta 7.69 (s, 4H), 7.59 (d, J = 8.1Hz, 2H), 7.49 (d, J = 8.1Hz, 2H), 4.64 (s, 2H); 13C-NMR (CDCI3, 150 MHz) delta: 144.2, 140.0, 137.6, 129.8, 129.4, 127.8, 127.6, 125.9, 120.3, 45.9; ESI-MS m/z for Ci4HnF30 [M + H]+, [M + Na]+;
With methanesulfonyl chloride; triethylamine; In dichloromethane; for 18h; The product from Example 3A was dissolved in 10 ml methylene chloride. Triethylamine (468 mg, 4.62 mol) and methanesulfonyl chloride (422 mg, 3.68 mmol) were then added and stirred for 18 h. The reaction was poured into water and extracted with methylene chloride. The organic solution was dried over anhydrous sodium sulfate, decanted and concentrated to provide the title compound that was used without further purification. MS m/z 235 (M-Cl+1).

 

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