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CAS No. : | 59447-06-2 | MDL No. : | MFCD00142586 |
Formula : | C6H2BrClF2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OKGLKEDYKFGKOW-UHFFFAOYSA-N |
M.W : | 227.43 | Pubchem ID : | 2773255 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.07 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
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) : | -5.24 cm/s |
Log Po/w (iLOGP) : | 2.22 |
Log Po/w (XLOGP3) : | 3.44 |
Log Po/w (WLOGP) : | 4.22 |
Log Po/w (MLOGP) : | 4.48 |
Log Po/w (SILICOS-IT) : | 4.02 |
Consensus Log Po/w : | 3.68 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.86 |
Solubility : | 0.0313 mg/ml ; 0.000138 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.12 |
Solubility : | 0.172 mg/ml ; 0.000757 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.43 |
Solubility : | 0.00843 mg/ml ; 0.0000371 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.82 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P302+P352 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
73.7% | With potassium carbonate;palladium(0)bis(tricyclohexylphosphine); In 1,4-dioxane; water; at 85℃; for 4h; | 2'-Chloro-4',5'-difluoro-biphenyl-4-ol; 4-Chloro-1,2-difluoro-benzene (12 g, 80.79 mmol) and iron (4.524 g, 80.79 mmol) were mixed with bromine (4.57 mL, 88.87 mmol) and the flask was wrapped with aluminum foil. After stirring at room temperature for 30 min, the mixture was heated on an oil bath at 72 C. overnight. The mixture was cooled to room temperature and aqueous HCl solution (1.0N, 45 ml) was added. The reaction mixture was extracted with methylene chloride and the organic phase was washed with brine, dried and concentrated. The resulting oil was purified using an ISCO (220 g) column chromatography, eluting with hexanes to obtain 1-bromo-2-chloro-4,5-difluoro-benzene as an oil. (8.1 g, 44.1%). 1H NMR (300 MHz, CDCl3) δ ppm 7.47 (t, J=8.6 Hz, 1H), 7.33 (dd, J=9.5, 7.4 Hz, 1H).Bromo-2-chloro-4,5-difluoro-benzene (5.9 g, 25.95 mmol) and 4-hydroxyphenyl-boronic acid (4.29 g, 31.13 mmol) were suspended in 138 ml of dioxane. Potassium carbonate (4.483 g, 32.43 mmol) in 40 ml water solution was added and after stirring for 10 minutes, bis(tricyclohexylphosphine)palladium(0) (530 mg, 0.779 mmol) was added. The reaction was stirred at 85 C. for 4 hrs and concentrated. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried and solvents were evaporated. The crude product was purified using an ISCO (120 g) column chromatography, eluting with 5-20% ethyl acetate in hexanes to obtain the crude product which was further recrystallized from hexane to afford 2'-chloro-4',5'-difluoro-biphenyl-4-ol as a white solid (4.6 g, 73.7%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.71 (s, 1H), 7.99 (dd, J=10.6, 7.5 Hz, 1H), 7.51 (dd, J=11.5, 8.8 Hz, 1H), 7.25 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H). LR-MS (ES) calculated for C12H7ClF2O, 240.64. found m/z 239 [M-H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; acetic acid; In water; at 12 - 50℃; for 3.7h; | First, 14.86 g (100 mmol) of <strong>[696-02-6]4-chloro-1,2-difluorobenzene</strong>, 15.73 g (55 mmol) of 1,3-dibromo-5,5-dimethylhydantoin and 70 mL of acetic acid were mixed, and the mixture was cooled to 12C. Subsequently, 30 mL of concentrated sulfuric acid was added to the mixture, and a reaction was performed at 50C for 1.7 hours. An additional 1.46 g (5.1 mmol) of 1,3-dibromo-5,5-dimethylhydantoin was then added, and the reaction was continued for 2 hours. Subsequently, the reaction mixture was extracted into 100 mL of hexane. The target compound was extracted from the waste acid layer using two 100 mL samples of hexane and then a further 30 mL of hexane. The organic layers were combined and washed twice with 50 mL samples of water, once with 50 mL of a saturated aqueous solution of sodium thiosulfate, twice with 20 mL samples of a 1 mol/L aqueous solution of sodium hydroxide, once with 30 mL of water, and then once with a saturated saline solution. Subsequently, the organic layer was concentrated under reduced pressure, yielding 17.36 g (yield: 76%) of 1-bromo-2-chloro-4,5-difluorobenzene as yellow crystals. |
44.1% | With bromine; iron; at 20 - 72℃; | 2'-Chloro-4',5'-difluoro-biphenyl-4-ol; 4-Chloro-1,2-difluoro-benzene (12 g, 80.79 mmol) and iron (4.524 g, 80.79 mmol) were mixed with bromine (4.57 mL, 88.87 mmol) and the flask was wrapped with aluminum foil. After stirring at room temperature for 30 min, the mixture was heated on an oil bath at 72 C. overnight. The mixture was cooled to room temperature and aqueous HCl solution (1.0N, 45 ml) was added. The reaction mixture was extracted with methylene chloride and the organic phase was washed with brine, dried and concentrated. The resulting oil was purified using an ISCO (220 g) column chromatography, eluting with hexanes to obtain 1-bromo-2-chloro-4,5-difluoro-benzene as an oil. (8.1 g, 44.1%). 1H NMR (300 MHz, CDCl3) delta ppm 7.47 (t, J=8.6 Hz, 1H), 7.33 (dd, J=9.5, 7.4 Hz, 1H).Bromo-2-chloro-4,5-difluoro-benzene (5.9 g, 25.95 mmol) and 4-hydroxyphenyl-boronic acid (4.29 g, 31.13 mmol) were suspended in 138 ml of dioxane. Potassium carbonate (4.483 g, 32.43 mmol) in 40 ml water solution was added and after stirring for 10 minutes, bis(tricyclohexylphosphine)palladium(0) (530 mg, 0.779 mmol) was added. The reaction was stirred at 85 C. for 4 hrs and concentrated. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried and solvents were evaporated. The crude product was purified using an ISCO (120 g) column chromatography, eluting with 5-20% ethyl acetate in hexanes to obtain the crude product which was further recrystallized from hexane to afford 2'-chloro-4',5'-difluoro-biphenyl-4-ol as a white solid (4.6 g, 73.7%). 1H NMR (300 MHz, DMSO-d6) delta ppm 9.71 (s, 1H), 7.99 (dd, J=10.6, 7.5 Hz, 1H), 7.51 (dd, J=11.5, 8.8 Hz, 1H), 7.25 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H). LR-MS (ES) calculated for C12H7ClF2O, 240.64. found m/z 239 [M-H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | To a solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (22 mL, 11 mmol, 0.5 M) at 25 C under argon was added tert-butyl 4-methylenepiperidine-1-carboxylate (2.17 g, 11 mmol). The mixture was stirred at 65 C for 2 h. The mixture was cooled down to 25 C and added to a solution of 1-bromo-2- chloro-4,5-difluorobenzene (2.5 g, 11 mmol), potassium carbonate (1.97 g, 14.3 mmol) and 1,1’- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (449 mg, 0.55 mmol) in N,N-dimethylformamide/water (17.6 mL/1.76 mL) at 25 C. The resulting mixture was heated at 60 C for 20 h. The reaction was quenched with 1 N aqueous sodium hydroxide solution and the aqueous layer was stirred at 25 C for 1 h. The solution was diluted with ethyl acetate (200 mL) and washed with brine (150 mL x 3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, petroleum ether / ethyl acetate = 33/1) to give tert-butyl 4-(2-chloro-4,5-difluorobenzyl)piperidine-1-carboxylate (430 mg, 1.25 mmol, 11%) as a colorless oil. LCMS (ESI) m/z: 290.0 [M-56+H]+. |
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