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CAS No. : | 407-14-7 | MDL No. : | MFCD00040834 |
Formula : | C7H4BrF3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SEAOBYFQWJFORM-UHFFFAOYSA-N |
M.W : | 241.01 | Pubchem ID : | 521008 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.83 |
TPSA : | 9.23 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) : | -4.75 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 4.26 |
Log Po/w (WLOGP) : | 4.61 |
Log Po/w (MLOGP) : | 3.03 |
Log Po/w (SILICOS-IT) : | 3.06 |
Consensus Log Po/w : | 3.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.26 |
Solubility : | 0.0134 mg/ml ; 0.0000555 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.17 |
Solubility : | 0.0165 mg/ml ; 0.0000683 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.88 |
Solubility : | 0.0316 mg/ml ; 0.000131 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.55 |
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 |
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 |
---|---|---|
71 %Spectr. | With Et3NHF*5HF; iodine pentafluoride-pyridine-hydrogen fluoride In 1,2-dichloro-ethane at 60℃; for 24 h; | General procedure: To IF5-pyridine-HF (321 mg, 1.0 mmol) in dichloroethane (2 mL), were added Et3N-6HF (553 mg, 2.5 mmol) and 2a (113 mg, 0.5 mmol) successively at room temperature. The mixture was stirred at 60 °C for 9 h. The resulting dark red solution was poured into water (20 mL) and extracted with CH2Cl2 (20 mL * 3). The combined organic layer was washed with aq NaHCO3 and aq Na2S2O3, and dried over MgSO4. The yield of 4a was determined to be 74percent by 19F NMR using fluorobenzene as an internal standard. Pure 4a was obtained by column chromatography (silica gel/hexane); IR (neat) 2963, 1256, 1212 cm-1; 1H NMR δ 7.23 (d, J = 8.8 Hz, 2H), 7.13 (d, J = 8.4 Hz, 2H), 2.95-2.85 (m, 1H), 1.24 (d, J = 6.8 Hz, 6H); 19F NMR δ-58.53 (s, 3F); 13C NMR δ 147.7, 147.3, 127.8 (2C), 121.0 (2C), 120.7 (q, 1JC-F = 257.7 Hz), 33.7, 24.1 (2C); HRMS (EI) calcd for C10H11F3O 204.07620, found 204.07606. |
70 %Spectr. | With Et3NHF*5HF; iodine pentafluoride-pyridine-hydrogen fluoride In 1,2-dichloro-ethane at 60℃; for 24 h; | Products were synthesized in the same manner as in Example 1, except that the substrate (compound 1a), reaction temperature, time, and solvent used in Example 1-1 were changed to those shown in Table 2.Regarding the “yield/percent” in Table 2, the 19F-NMR yield is based on the substrate. The value in parenthesis is an isolation yield. In air, IF5-pyridine-HF (321 mg, 1.00 mmol) and Et3N-6HF (553 mg, 2.50 mmol) were added to methylene chloride (1 mL) in a Teflon (trade name) container, and compound 1a (O-(4-isopropyl phenyl)S-methyl dithiocarbonate) (0.5 mmol) was added thereto at room temperature, followed by stirring at 60° C. for nine hours. The reaction mixture was added to water (30 mL), and extraction was performed using methylene chloride three times (20 mL×3). The organic layer was washed with a saturated sodium bicarbonate aqueous solution (20 mL) and a saturated sodium thiosulfate aqueous solution (20 mL), and then dried with magnesium sulfate. After condensation, product 2a (trifluoromethyl 4-isopropyl phenyl ether) was obtained by silica gel column chromatography (hexane ether) with a yield of 74percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.8% | at 100℃; for 16 h; | Step 2 1-bromo-4-(trifluoromethoxy)benzene Trifluoromethoxybenzene 6c (11.35 g, 70 mmol) was dissolved in 3.57 mL liquid bromine, followed by addition of iron (0.24 g). The reaction mixture was stirred for 16 hours at 100° C. 450 mL of dichloromethane were added and the organic extract was washed with 6 M hydrochloric acid (140 mL), 10percent sodium hydrogen sulfite solution (140 mL) and saturated sodium chloride solution (140 mL), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound 1-bromo-4-(trifluoromethoxy)benzene 6d (14.1 g, yellow solid), yield: 83.8percent. 1H NMR (400 MHz, CDCl3): δ 7.54-7.50 (m, 2H), 7.11-7.09 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: With magnesium; ethylene dibromide In tetrahydrofuranInert atmosphere Stage #2: With C10H17NO In tetrahydrofuran; toluene at -20℃; for 2 h; Inert atmosphere |
General procedure: To a flame-dried 25 mL round bottom flask was charged activated Mg (7.5 mmol, 1.5 eq.) and 5 mL anhydrous THF. To this suspension was added 2 drops of 1,2-dibromoethane. After 5 min, a solution of Aryl bromide (5 mmol, 1.0 eq.) in 5 mL anhydrous THF was slowly added to the suspension of Mg at room temperature. The reaction was mildly exothermic. The Grignard reagent was titrated and 1 mmol of this reagent was added to a flame-dried reaction vial. The solution was diluted with 3 mL anhydrous toluene and after cooling to the target temperature T, a solution of oxaziridine (1.2 mmol, 1.2 eq.) in 1 mL anhydrous toluene was added. The reaction was maintained at the targeted temperature T for time t before being quenched with saturated aqueous NH4Cl. (The actual temperature/reaction time is listed for each substrate.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | Heating / reflux | 4-(Trifluoromethoxy)benzonitrile: To a solution of 1-bromo-4-(trifluoromethoxy)benzene (24 g, 99.6 mmol) in DMF (120 mL) was added CuCN (19.7 g, 200.0 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was quenched by adding H2O/ice (200 mL) and the resulting solution was extracted from EtOAc (3.x.200 mL). The combined organic solution was dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (1:20 EtOAc/hexanes) to give the title compound (4 g, 21percent) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | With hydrogenchloride; n-butyllithium; sodium chloride In tetrahydrofuran; n-heptane | EXAMPLE 1E 4-(trifluoromethoxy)phenylboronic Acid A solution of 1-bromo-4-(trifluoromethoxy)benzene (1.69 kg) and triisopropyl borate (1.46 kg) in THF (6.75 L) at -70° C. was treated with 2.25 M butyllithium in hexanes (3.27 L) over 2.3 hours, stirred for 10 minutes, treated with 6M HCl (1.52 L) over 50 minutes, stirred for 18 hours at room temperature, and poured into a mixture of heptane (8.43 L) and 20percent (w/w) sodium chloride (8.44 kg). This mixture was stirred for 10 minutes and separated into an aqueous fraction and an organic fraction. The organic fraction was concentrated to provide a white paste. The paste was dried under vacuum (100 mmHg) at ambient temperature with a nitrogen bleed for 2 days then at 40-50° C. for 18 hours to provide 1.306 kg (90.4percent) of the desired product as a solid. 1H NMR (CDCl3, 300 MHz) δ 7.24-7.19 (m, 2H), 8.14-8.10 (m, 2H) with additional absorptions at 7.19-7.15 (m, 2H) and 8.04-8.00 (m, 2H) corresponding to the cyclic boronic acid trimer. |