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CAS No. : | 352535-97-8 | MDL No. : | MFCD05664228 |
Formula : | C6H5BBrFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QCLOSORNRRMFIA-UHFFFAOYSA-N |
M.W : | 218.82 | Pubchem ID : | 16217170 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.93 |
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) : | -6.48 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.62 |
Log Po/w (WLOGP) : | 0.69 |
Log Po/w (MLOGP) : | 1.48 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 0.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.55 |
Solubility : | 0.61 mg/ml ; 0.00279 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.81 mg/ml ; 0.00828 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.43 |
Solubility : | 0.819 mg/ml ; 0.00374 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.1 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
EXAMPLE 3 2-Hexyloxy-1,6,7,8-tetrafluorophenanthrene 290 ml of a 1.6 molar solution of butyllithium in hexane are added dropwise at -70 C. to a solution of 112 g of 2,6-dibromofluorobenzene [1435-54-7] in 1000 ml of diethyl ether. After the mixture has been kept at the same temperature for 2 hours, 60 ml of trimethyl borate are added, and the mixture is stirred at this temperature for 12 hours. After the mixture has been slowly warmed to room temperature, 300 ml of water are added, and the pH is adjusted to 1 by addition of hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted twice with 100 ml of ether each time, and the combined organic phases are dried under reduced pressure, giving 91 g of 3-bromo-2-fluorophenylboronic acid (mixed with its cyclic anhydride) as a brown solid; 1H-NMR (DMSO-d6): 7.1-7.7 (m) ppm, 19F-NMR (DMSO-d6): -99 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 85.0℃; for 3h; | To <strong>[659731-48-3]5-chloro-2-fluoro-4-iodopyridine</strong> (400 mg, 1.554 mmol) was added 3-bromo-2- fluorophenylboromc acid (340 mg, 1.554 mmol), PdCl2(dppf).CH2C12 adduct (127 mg, 0.155 mmol), DME (6.8 ml) and last 2M sodium carbonate (2.331 ml, 4.66 mmol). The reaction was stirred at 85 C for 3 hr. The reaction was followed by LCMS. The reaction was cooled, 15 ml of ethyl acetate and 5 ml of methanol was added, filtered and concentrated to crude product. The crude was purified by silica gel chromatography using 40g column eluting with 0%-10% ethyl acetate with heptane. The desired fractions were concentrated to constant mass, giving 250 mg of the titled compound as free base used without further purification. LCMS (m/z): 304.0/306.0 (MH+), rt = 1.07 mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride; In ethanol; water; at 100.0℃;Microwave irradiation; | Similar to as described in General Procedure X, 2-chloropyrimidine-4-carboxamide was reactedwith <strong>[352535-97-8](3-bromo-2-fluorophenyl)boronic acid</strong> to afford the title compound (450 mg, 48%) as ayellow solid. LC-MS (ES, m/z): 296 [M+H]. Aryl halide, palladium (II) bis(triphenylphosphine) dichloride or tetrakis (triphenylphosphine) palladium (0.OSeq), boronic acid or pinacol ester (1. leq) and cesium fluoride (2eq) were weighed out into a microwave vessel or sealed tube. Ethanol (3 mL/mmol) and water (0.6 mL/mmol) were added. The vessel was capped and heated thermally or in a microwave vessel at 70-400 C for 1 hour. The reaction mixture was concentrated under vacuum and the residue was purified by silicagel column chromatography to afford the Suzuki coupling product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100.0℃; for 1h;Inert atmosphere; | To a schlenck flask was added <strong>[352535-97-8](3-bromo-2-fluorophenyl)boronic acid</strong> (0.5 g, 2.28 mmol), 2-bromopyridine (0.32 mL, 3.43 mmol), tetrakis(triphenylphosphine)palladium(0) (0.26 g, 0.23 mmol), iN Na2CO3 (6.9 mL, 6.86 mmol), followed by 1,4-dioxane (10 mL) and was degassed under an atmosphere of argon for 5 mm and was heated at 100C for 1 h. The reaction was cooled, filtered through a pad of celite, washed with iN Na2CO3, water and brine, dried over sodium sulfate, and concentrated. The product was purified via silica gel chromatography (10%ethyl acetate/hexanes) and concentrated to give 2-(3-bromo-2-fluoro-phenyl)-pyridine (0.54 g, 94%). Analysis: LCMS m/z = 253 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Inert atmosphere; Reflux; | (3?-Bromo-2-fluorophenyl)boronic acid (30.0 g, 137 mmol) and 2,4-dichloro-6-iodophenol (43.6 g, 150 mmol) were added to 400 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (56.8 g, 411 mmol) was added by dissolving in 150 ml of water and thoroughly stirred. Tetrakistriphenyl-phosphinopalladium (4.8 g, 4 mmol) was then added thereto. After reaction for 12 hours, the temperature was lowered to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was dried, and then subjected to column chromatography with hexane and ethyl acetate to give Compound 4?A (36.9 g, 80%). |
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