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Product Details of [ 103889-37-8 ]

CAS No. :103889-37-8 MDL No. :MFCD03412198
Formula : C7H3ClF4 Boiling Point : -
Linear Structure Formula :- InChI Key :ILUCOEVDXAZECW-UHFFFAOYSA-N
M.W : 198.55 Pubchem ID :16743980
Synonyms :

Safety of [ 103889-37-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 103889-37-8 ]

* 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 [ 103889-37-8 ]

[ 103889-37-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 103889-37-8 ]
  • [ 6419-36-9 ]
  • <i>N</i>-(4-chloro-2-fluoro-3-trifluoromethyl-phenyl)-2-pyridin-3-yl-acetamide [ No CAS ]
  • [ 899431-57-3 ]
  • 2
  • [ 103889-37-8 ]
  • [ 870065-92-2 ]
  • 1-chloro-3-fluoro-4-nitro-2-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; at 0 - 20℃; for 2.5h; To a solution of conc. H2S04 (3 mL) and conc. HNO3 (3 mL) was added 1-chloro- 3-fluoro-2-(trifluoromethyl)benzene (1.00 g, 5.05 mmol) at 0C. The reaction mixture was stirred at 0C for 30 minutes and at room temperature for 2 h, then poured into icecold H20 (50 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was washed with H20 (100 mL) and brine (100 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford the title compounds (mixture of isomers; 1.00 g, 82%) as a yellow liquid. oH (400 MHz, CDC13 mixture of isomers) 7.21-7.40 (m, 1H), 7.51 (d, J 8.80 Hz, 1H), 7.95 (d, J 3.42 Hz, 1H), 8.17 (br s, 1H).
  • 3
  • [ 103889-37-8 ]
  • 4-chloro-2-fluoro-3-(trifluoromethyl)aniline [ No CAS ]
  • 2-chloro-4-fluoro-3-trifluoromethylphenylamine [ No CAS ]
  • 4
  • [ 103889-37-8 ]
  • [ 899431-61-9 ]
  • 5
  • [ 103889-37-8 ]
  • [ 870065-92-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 0.666667h; Concentrated nitric acid (12.6 mL) and concentrated sulfuric acid (12.6 niL) were combined at 0 C and treated with neat l-chloro-3-fluoro-2-(trifluoromethyl)benzene (5.36 g, 26.5 mmol) dropwise with stirring. The mixture was stirred at 0 0C for 10 minutes, allowed to warm to room temperature over 30 minutes, and poured into a beaker containing ice (50 g). The mixture was extracted with dichloromethane (3 x 30 mL). The organic extracts were combined, dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel/ 10% ethyl acetate in hexanes, product Rf = 0.5) to provide an inseparable mixture of the title compound and a regioisomer. 1H NMR (CDCl3) major regioisomer delta 7.97 (dd, IH), 7.33 (dd, IH); minor regioisomer delta 8.18 (dd, IH), 7.53 (d, IH).
YieldReaction ConditionsOperation in experiment
The following illustrative compounds are among those obtained according to the process of the invention: ... 4-nitrotrifluoromethylbenzene, 3,4-dichlorotrifluoromethylbenzene, 2-nitrotrifluoromethylbenzene, 2,6-difluorotrifluoromethylbenzene, 2-chloro-6-fluorotrifluoromethylbenzene, 4-chloropentafluoroethoxybenzene, pentafluoroethoxybenzene, alpha,alpha-difluoro-beta,beta,beta-trichloroethoxybenzene, ...
  • 7
  • [ 1262116-32-4 ]
  • [ 103889-37-8 ]
  • C20H27ClF3NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
(S)-3-((R)-2-Ethylsulfanyl-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (10 mg, 40 mumol) was dissolved in DMF (174 muL). NaH (1.3 mg, 54.5 mumol) was added and the mixture was stirred at room temperature for 15 minutes. 2-Chloro-6-fluorobenzotrifluoride (21.6 mg, 109 mumol) was added and the mixture was stirred at 100 C. for 1 hour. The mixture was cooled to room temperature, concentrated then dissolved in 1.2M HCl in EtOH (890 muL, 1.1 mmol) and stirred overnight at room temperature. The product was concentrated and the crude product was dissolved in 1:1 AcOH/H2O (1.5 mL) then purified by preparative HPLC to yield the title compound as a mono-TFA salt (3.4 mg, purity 97%). MS m/z: [M+H]+ calcd for C15H19ClF3NOS, 354.08; found 354.0.
  • 8
  • [ 1262116-33-5 ]
  • [ 103889-37-8 ]
  • C21H29ClF3NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
(S)-3-((R)-1-Hydroxy-2-isopropylsulfanylethyl)pyrrolidine-1-carboxylic acid t-butyl ester (10 mg, 0.030 mumol) was dissolved in DMF (166 muL). NaH (1.7 mg, 69.1 mumol) was added and the mixture was stirred at room temperature for 15 minutes. 2-Chloro-6-fluorobenzotrifluoride (20.6 mg, 104 mumol) was added and the mixture was stirred at 100 C. for 1 hour. The mixture was cooled to room temperature, concentrated then dissolved in 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) and stirred overnight at room temperature. The product was concentrated and the crude product was dissolved in 1:1 AcOH/H2O (1.5 mL) then purified by preparative HPLC to yield the title compound as a mono-TFA salt (9.2 mg, purity 94%). MS m/z: [M+H]+ calcd for C16H21ClF3NOS, 368.10; found 368.0.
  • 9
  • [ 103889-37-8 ]
  • [ 68-12-2 ]
  • (4-chloro-2-fluoro-3-(trifluoromethyl)phenyl)methanediol [ No CAS ]
  • 4-chloro-2-fluoro-3-(trifluoromethyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a mixture of l-chloro-3-fluoro-2-(trifluoromethyl)benzene (2 g, 10 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise 2 M lithium diisopropylamide (2.0 M in tetrahydrofuran/n-heptane, 7.6 mL, 15 mmol). The mixture was stirred for 1 hour, and then N, N-dimethylformamide (0.9 g, 12 mmol) was added dropwise at -70 C. The reaction was stirred at -70 C for another 1 hour, then quenched by addition of water (20 mL), acidified to pH 2 with concentrated hydrochloric acid at 0 C, and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated brine (3 x 10 mL), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give compound mixture B-185 (1.7 g, 11: 1 ratio of hydrate: aldehyde) as a yellow solid. -NMR (CD3OD, 400 MHz): delta 10.27 (s, 1H), 8.09-8.03 (m, 1H), 7.81 (t, J=8.0 Hz, 11H), 7.60 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.8 Hz, 11H), 5.75 (s, 11H).
  • 10
  • [ 103889-37-8 ]
  • [ 2365-48-2 ]
  • [ 68-12-2 ]
  • methyl 6-chloro-7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.4 g To a mixture of l-chloro-3-fluoro-2-(trifluoromethyl)benzene (2 g, 10 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise 2 M lithium diisopropylamide (2.0 M in tetrahydrofuran/n-heptane, 7.6 mL, 15 mmol). The mixture was stirred for 1 hour, and then N, N-dimethylformamide (0.9 g, 12 mmol) was added dropwise at -70 C. The reaction was stirred at -70 C for another 1 hour, then quenched by addition of water (20 mL), acidified to pH 2 with concentrated hydrochloric acid at 0 C, and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated brine (3 x 10 mL), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give compound mixture B-185 (1.7 g, 11: 1 ratio of hydrate: aldehyde) as a yellow solid. -NMR (CD3OD, 400 MHz): delta 10.27 (s, 1H), 8.09-8.03 (m, 1H), 7.81 (t, J=8.0 Hz, 11H), 7.60 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.8 Hz, 11H), 5.75 (s, 11H). To a solution of compound mixture B-185 (0.5 g, 2 mmol) in dichloromethane (5 mL) was added triethylamine (0.3 g, 3 mmol) and methyl 2-sulfanylacetate (0.3 g, 3 mmol). The mixture was stirred at 40 C for 20 hours, then diluted with water (40 mL) and extracted with ethyl acetate (3 chi 40 mL). The combined organic layers were washed with brine (3 x 10 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10: 1] to give compound B-186 (0.4 g, 70% yield) as a white solid. -NMR (CD3OD, 400 MHz): delta 8.14 (d, J=6.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 1H), 3.96 (s, 3H).
  • 11
  • [ 103889-37-8 ]
  • 6-chloro-7-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]
  • 12
  • [ 103889-37-8 ]
  • [ 68-12-2 ]
  • 4-chloro-2-fluoro-3-(trifluoromethyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% To a solution of l-chloro-3-fluoro-2-(tnfluoromethyl)benzene (0.50 g, 2.5 mmol) at -70 C was added dropwise lithium diisopropylamide (2 M in tetrahydrofuran, 3.8 mmol, 1.9 mL). The reaction was stirred at -70 C for 0.5 hour, then 1V N - dimethylformamide (0.55 g, 7.6 mmol) was added slowly, and stirring was continued at -70 C for another hour. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were concentrated in vacuo, and the residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10:11 to give B-34 (0.40 g, 70% yield) as a yellow solid. 1H-NMR (CDC13, 400 MHz): M0.28 (s, 1H), 7.95-7.90 (t, J=l0.0 Hz, 1H), 7.40-7.37 (d, J=l 1.2 Hz, 1H).
0.4 g To a solution of l-chloro-3-fluoro-2-(trifluoromethyl)benzene (0.50 g, 2.5 mmol) at - 70 C was added dropwise lithium diisopropylamide (2 M in tetrahydrofuran, 3.8 mmol, 1.9 mL). The reaction was stirred at -70 C for 0.5 hour, then N, N - dimethylformamide (0.55 g, 7.6 mmol) was added slowly, and stirring was continued at -70 C for another hour. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were concentrated in vacuo, and the residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10: 1] to give A-46 (0.40 g, 70% yield) as a yellow solid. 1H-NMR (CDCI3, 400 MHz): 510.28 (s, IH), 7.95-7.90 (t, J=10.0 Hz, IH), 7.40-7.37 (d, J=l 1.2 Hz, IH).
  • 13
  • [ 103889-37-8 ]
  • C8H4ClF4NO [ No CAS ]
  • 14
  • [ 103889-37-8 ]
  • 1-chloro-3-fluoro-4-nitro-2-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With sulfuric acid; nitric acid; at 0 - 20℃; for 2.5h; To a solution of cone. H2S04 (3 mL) and cone. HNO3 (3 mL) was added 1-chloro- 3-fluoro-2-(trifluoromethyl)benzene (1.00 g, 5.05 mmol) at 0C. The reaction mixture was stirred at 0C for 30 minutes, then at room temperature for 2 h. The reaction mixture was poured into ice-cold H20 (50 mL) and extracted with EtOAc (2 x 50 mL). Theorganic layer was washed with H20 (100 mL) and brine (100 mL), then separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford a mixture of the title compound and 2-chloro-4-fluoro- 1 -nitro-3 -(trifluoromethyl)benzene (1.00 g, 82%) as a yellow liquid. oH (400 MHz, CDC13, mixture of isomers) 7.21-7.40(m, 1H), 7.51 (d, J8.80 Hz, 1H), 7.95 (d, J3.42 Hz, 1H), 8.17 (br s, 1H).
  • 15
  • [ 103889-37-8 ]
  • tert-butyl (NE)-N-[(5R)-5-(3-amino-2-fluorophenyl)-2,5-dimethyl-1,1-dioxo-1,2,4-thiadiazinan-3-ylidene]carbamate [ No CAS ]
  • tert-butyl (NE)-N-[(5R)-5-{3-[3-chloro-6-nitro-2-(trifluoromethyl)anilino]-2-fluorophenyl}-2,5-dimethyl-1,1-dioxo-1,2,4-thiadiazinan-3-ylidene]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of conc. H2S04 (3 mL) and conc. HNO3 (3 mL) was added 1-chloro- 3-fluoro-2-(trifluoromethyl)benzene (1.00 g, 5.05 mmol) at 0C. The reaction mixture was stirred at 0C for 30 minutes and at room temperature for 2 h, then poured into icecold H20 (50 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was washed with H20 (100 mL) and brine (100 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford the title compounds (mixture of isomers; 1.00 g, 82%) as a yellow liquid. ; To a solution of Intermediate 6 (0.25 g, 0.64 mmol) and Intermediate JO (as a mixture of isomers) (0.78 g, 3.23 mmol) in THF (12 mL) was added 1.8M tert-butyl10 lithium solution (1.90 mL, 3.23 mmol) dropwise at -78C. The reaction mixture wasstirred at -78C for 30 minutes and at room temperature for 16 h, then quenched with brine (100 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was separated, and washed with H20 (100 mL) and brine (100 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography(silica, 100-200 mesh, 30% EtOAc in hexanes) to afford the title compound (80% purity by LCMS) (0.12 g, 30%) as a yellow solid. oH (400 MHz, CDC13) 1.58 (m, 9H), 1.92 (s, 3H), 3.25 (s, 3H), 3.72 (d, J 14.1 Hz, 1H), 4.22 (d, J 14.1 Hz, 1H), 6.81 (t, J7.9 Hz, 1H),6.94-7.08 (m, 2H), 7.36 (d, J8.9 Hz, 1H), 7.95 (s, 1H), 8.13 (d, J8.9 Hz, 1H), 10.62 (s, 1H). LCMS (Method 1, ES+) 594 [M+lf?, 3.81 minutes.
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