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CAS No. : | 1186403-17-7 | MDL No. : | MFCD13189469 |
Formula : | C6H5BBrClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YLKZHZVQNASRAN-UHFFFAOYSA-N |
M.W : | 235.27 | Pubchem ID : | 53216753 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 48.98 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.21 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.15 |
Log Po/w (WLOGP) : | 0.78 |
Log Po/w (MLOGP) : | 1.64 |
Log Po/w (SILICOS-IT) : | 0.61 |
Consensus Log Po/w : | 1.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.99 |
Solubility : | 0.24 mg/ml ; 0.00102 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.63 |
Solubility : | 0.549 mg/ml ; 0.00233 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.76 |
Solubility : | 0.406 mg/ml ; 0.00173 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
64.5% | Example 24: Preparation 1-bromo-3-chloro-5-(2,2,2-trifluoroethyl)benzene (C146) (0729) (0730) 638 (3-Bromo-5-chlorophenyl)boronic acid (4 g, 17.00 mmol) was added to a flask with 639 <strong>[373-88-6]2,2,2-trifluoroethan-1-amine hydrochloride</strong> (9.22 g, 68.0 mmol), 640 sodium nitrite (5.87 g, 85 mmol), and 641 ammonium chloride (3.64 g, 68.0 mmol). The reaction was heated to 100 C. overnight. At this point, the solvent was removed, and the residue was dissolved in 632 dimethyl sulfoxide (20 mL). 642 Potassium fluoride (1.976 g, 34.0 mmol) was added, and the mixture was heated to 100 C. for 2 hours. After cooling, the mixture was diluted with water and extracted with dichloromethane. After extraction and solvent removal, the residue was purified by silica gel chromatography eluting with hexanes. The 643 title compound was recovered as a clear, colorless oil that crystallized upon standing (3.00 g, 64.5%): 1H NMR (300 MHz, CDCl3) delta 7.52 (t, J=1.8 Hz, 1H), 7.35 (s, 1H), 7.24 (s, 1H), 3.32 (q, 1=10.5 Hz, 2H). 19F NMR (471 MHz, CDCl3) delta -65.64. ESIMS m/z 274 ([M+H]+). | |
With ammonium chloride; potassium fluoride; sodium nitrite; | Example 39 Preparation 1-Bromo-3-chloro-5-(2,2,2-trifluoroethyl)benzene (C181) (3-Bromo-5-chlorophenyl)boronic acid (4 g, 17.00 mmol) was added to a flask with <strong>[373-88-6]2,2,2-trifluoroethan-1-amine hydrochloride</strong> (9.22 g, 68.0 mmol), sodium nitrite (5.87 g, 85 mmol), and ammonium chloride (3.64 g, 68.0 mmol). The reaction was heated to 100 C. overnight. At this point, the solvent was removed, and the residue was dissolved in dimethyl sulfoxide (20 mL). Potassium fluoride (1.976 g, 34.0 mmol) was added, and the mixture was heated to 100 C. for 2 hours. After cooling, the mixture was diluted with water and extracted with dichloromethane. After extraction and solvent removal, the residue was purified by silica gel chromatography eluting with hexanes. The title compound was recovered as a clear, colorless oil that crystallized upon standing (3.00 g, 64.5%): 1H NMR (400 MHz, CDCl3) delta 7.52 (t, J=1.8 Hz, 1H), 7.35 (s, 1H), 7.24 (s, 1H), 3.32 (q, J=10.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) 5-65.64; ESIMS m/z 274.0 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃;Inert atmosphere; | To a 3 L reaction flask was charged 96 g (279.22 mmol, 1.0 eq) of compound [6-2], 98.54 g (418.84 mmol, 1.5 eq) of (3-bromo-5-chlorophenyl)boronic acid, 770 ml. (8 ml/g) of 1,4-dioxane was stirred at 60 C under a nitrogen atmosphere. At a temperature of 60 C, 6.45 g (5.58 mmol, 0.02 eq) of tetrakis(triphenylphosphine)palladium was added.(0), 57.898 (418.84 mmol, 1.5 A) of potassium carbonate was dissolved in 150 ml of distilled water and added, and stirred under reflux overnight. The reaction solution was cooled to room temperature and filtered. The solid was washed with methanol and distilled water. Recrystallization was carried out using toluene to prepare 83 g (60%) of an intermediate compound [6-3] as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In diethyl ether; at 20℃; for 4.0h;Inert atmosphere; Molecular sieve; | General procedure: To a Et2O solution of anorganoboronic acid (1.00 equiv) and 2,2-dimethylpropane-1,3-diol (neopentyl glycol)(1.02 equiv), 4A molecular sieves was added and the reaction mixture was stirred atroom temperature. After the reaction finished, the reaction mixture was filtered andconcentrated in vacuo. The residue was subjected to flash column chromatography(eluent: petroleum ether/ethyl acetate) or recrystallization to obtain the desired product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.1% | With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate; In ethanol; water; toluene; at 76℃; for 8.0h;Inert atmosphere; | Combine 2-chloro-4,6-diphenyl-1,3,5-triazine (20g, 74.70mmol), <strong>[1186403-17-7]3-bromo-5-chlorophenylboronic acid</strong> (21.09g, 89.64mmol), and tetrakis (triphenyl Phosphine) palladium (4.32g, 3.73mmol), potassium carbonate (20.64g, 149.41mmol), tetrabutylammonium chloride (1.01g, 3.73mmol), toluene (24mL), ethanol (12mL) and deionized water (6mL ) Added to a three-necked flask, heated to 76 C under nitrogen protection, heated to reflux and stirred for 8h. After the reaction was completed, the solution was cooled to room temperature, the reaction solid was precipitated, filtered with suction, rinsed with water, and then stripped with ethanol to obtain a gray solid. The crude product was purified by silica gel column chromatography to obtain intermediate II-B-1 (25.88g , Yield 82.10%). |
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