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CAS No. : | 1256355-30-2 | MDL No. : | MFCD09953731 |
Formula : | C7H6BFO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLYQNYPIYYNUCW-UHFFFAOYSA-N |
M.W : | 167.93 | Pubchem ID : | 46739727 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 41.61 |
TPSA : | 57.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.39 |
Log Po/w (WLOGP) : | -0.26 |
Log Po/w (MLOGP) : | 0.08 |
Log Po/w (SILICOS-IT) : | -0.16 |
Consensus Log Po/w : | 0.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.36 |
Solubility : | 7.25 mg/ml ; 0.0432 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.16 |
Solubility : | 11.5 mg/ml ; 0.0685 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.51 |
Solubility : | 5.2 mg/ml ; 0.031 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
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 |
---|---|---|
86% | General procedure: 4.2. General procedure for the synthesis of 3aA-3jA, 3aB-aE, 3bE as exemplified for 3aA: A suspension of 1a (0.20 g, 0.59 mmol), 2-formylphenylboronic acid 2A (0.09 g, 0.65 mmol), 2(M) aq Na2CO3 (0.13 g, 1.18 mmol) in dioxane (3 mL) was degassed under N2 for 15 min. Then a weighed amount of Pd(PPh3)4 (0.03 g, 0.03 mmol) was added to it and the reaction mixture was transferred to an oil bath and heated at 80 C until all the starting materials were consumed. The excess 2-propanol was evaporated under reduced pressure and the crude mixture was worked up with EtOAc (3*10 mL). Thereafter the combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and evaporated under reduced pressure to yield the crude product as brown oil, which after chromatographic purification [silica gel, hexane/EtOAc (80:20)] yielded the pure 3aA (0.18 g, 79%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.1% | A solution of ethyl 1 -(6-chloropyridin-2-yl)-5-(trifluoromethyl)- 1 H-pyrazole-4-carboxylate(10 g, 31.3 mmol), <strong>[1256355-30-2](5-fluoro-2-formylphenyl)boronic acid</strong> (7.88 g, 46.9 mmol, combiblocks) and Na2003 (6.63 g, 62.6 mmol) in 1 ,2-dimethoxyethane (25 mL) and water (5 mL) was purged with argon for 30 minutes at RT and then tetrakis(triphenylphosphine)palladium(0) (3.61 g, 3.13 mmol) was added. The reaction mixture was heated at 110 00 for 16 hours, then cooled and filtered on a celite pad. Thefiltrate was diluted with water (30 mL) and extracted with EtOAc (3x20 mL). The organic phase was washed with brine solution (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 10% of EtOAc - Hexane. Collected fractions were concentrated under reduced pressure to afford the title compound (7.5 g, 56.1 % yield) asbrown solid. LC/MS: rt=3.23min mlz= 408.4 [M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium tetrahydroborate; In methanol; at 20℃; for 7h; | To stirred solution of 5.05 g (30 mmol) of 4-fluoro-2-formylphenylboronic acid in 180 cm3 of methanol, 1.26 g of sodium borohydride (33.3 mmol) was added at room temperature in small portions (after addition of whole amount of NaBH4 the color of the solution turned from yellowish to almost colorless). The reaction mixture was stirred for 7 h at room temperature and additional 0.64 g of sodium borohydride (17 mmol) was added at room temperature. The resulting solution was stirred at room temperature overnight and was brought to pH ca. 3 by addition of 3 M aq. HCl at room temperature. Methanol was then removed under vacuum and yellowish suspension was obtained. The suspension was diluted with 25 ml of distilled water and 100 ml of saturated brine was added. Resulting mixture was extracted with 3 * 100 ml of ethyl acetate. The organic layers were combined and the solvent was removed under vacuum, giving 3.03 g of yellowish solid product (66% yield). 1H NMR (500 MHz, methanol-d4) 7.36 (m, 1H), 7.27 (m, 1H), 7.18 (m, 1H), 5.03 (s, 2H); 11B NMR (160.4 MHz, methanol-d4) 32.6; 13C NMR (125.7 MHz, methanol-d4) 164.8, 162.9, 150.7, 124.1 (d, J = 8 Hz), 119.2 (d, J = 23.5 Hz), 116.6 (d, J = 21 Hz), 72.0; single crystals of quality sufficient for X-ray investigation were obtained by two recrystallizations from, in sequence, water and tetrahydrofuran. Compounds 3 and 4 were obtained in similar way in 78% and 54% yield, respectively. It is noteworthy, that above synthetic method gives higher yields compared with those described for these compounds in literature [20] . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; | 2-Bromo-4,5,6,7-tetrahydrobenzo[d]thiazole (1.732 g, 7.94 mmol), (5-fluoro-2- formylphenyl)boronic acid (2.00 g, 11.91 mmol) and potassium carbonate (3.29 g, 23.82 mmol) were stirred in a solvent mixture of dioxane (20 mL) and water (25 mL) and purged with argon for 5 minutes. To the resulting reaction mixture was added palladium tetrakistriphenylphosphine (0.459 g, 0.397 mmol) and argon was purged for 5 minutes. The reaction mixture was heated overnight at 80 C then cooled to room temperature and filtered through celite. The filtrate was concentrated to give residue, which was dissolved in ethyl acetate, washed with water, brine solution, dried over sodium sulfate, concentrated and purified by flash chromatography to obtain the title compound, 4-fluoro-2-(4,5,6,7- tetrahydrobenzo[d]thiazol-2-yl)benzaldehyde as a solid. Yield: 1.6 g, 77 % yield; H NMR (300 MHz, CDC13): delta 10.49 (s, 1H), 8.09-8.04 (m, 1H), 7.41-7.37 (m, 1H), 7.24-7.18 (m, 1H), 2.88 (s, 4H), 1.94 (s, 4H); MS: 262 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.7% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 1.08333h;Inert atmosphere; | To a solution of 2-bromo-5-cyclopropylthiophene (2 g, 9.85 mmol) and (5-fluoro-2- formylphenyl)boronic acid (2.150 g, 12.80 mmol) in 10 mL dioxane: water (4: 1) mixture was added potassium carbonate (3.40 g, 24.62 mmol) and the mixture was purged with argon for 5 minutes. To the resulting solution palladiumtetrakistriphenylphosphine (0.683 g, 0.591 mmol) was added and argon was purged for 5 minutes. The reaction mixture was heated at 80 C for 1 h. After completion of reaction, the reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulfate, concentrated and purified by column chromatography on silica gel to obtain the title compound 2-(5-cyclopropylthiophen-2-yl)-4- fluorobenzaldehyde and colorless thick liquid. Yield: 1.74 g, 7.06 mmol, 71.7 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 2-Bromo-5-fluorobenzaldehyde (20.0 g, 98.5 mmol) was dissolved in 40 ml of methanol. 0.5 ml of concentrated H2SO4 was added and 13.6 g (128 mmol) of trimethyl orthoformate was added dropwise. The solution was refluxed for 1 h and left to cool down. Then the solution was brought to pH 11 with a concentrated solution of NaOMe in methanol. After distillation of the volatiles the product was distilled under vacuum to give 23.8 g of 1-bromo-2-(dimethoxymethyl)-4-fluorobenzene as a colorless liquid (yield 96.9%). 1H NMR (CDCl3, 500 MHz), delta/ppm: 7.51 (m, 1H), 7.35 (m, 1H), 6.93 (m, 1H), 5.50 (s, 1H), 3.38 (s, 6H). 23.8 g (95.0 mmol) of the above compound was dissolved in 200 ml of dry Et2O and 40 ml THF under argon flow. The solution was cooled down to -75 C using dry ice/acetone bath. 2.5 M n-butyllithium in hexanes (42.0 ml, 110.0 mmol) was added dropwise to keep the temperature under -70 C. The solution was stirred for 1 h, then 16.1 g (110.0 mmol) of triethyl borate was added slowly, keeping the temperature under -70 C. Cooling bath was removed and the solution was brought to pH 3 with 3 M aq. HCl, while the temperature rose to 5 C. The aqueous layer was separated and extracted with Et2O (2 × 50 ml). The organic layers were combined and the solvent was partially removed under vacuum. Distillation was continued after addition of water. The solid precipitated after cooling was filtered and dried on air, giving 14.3 g of 4-fluoro-2-formylphenylboronic acid (2) (yield 89.5%). 11B NMR (64 MHz, acetone-d6): delta = 30.9 ppm. Compounds 1, 3 and 4 were synthesized in similar way from the appropriate fluoro-substituted 2-bromobenzaldehydes. Overall (two-steps) yields are as follows: 1: 85.4%, 3: 78.3%, 4: 92.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium carbonate; In acetonitrile; at 23 - 24℃; for 0.5h; | General procedure: To a solution of the 2-formyl/acetyl-phenylboronic acid (3.00 mmol, 1.00 equiv.) in acetonitrile(5 ml) was added dimethyl phosphite (3.30 mmol, 1.10 equiv.) at 23-24 oC. To the above mixture was added potassium carbonate (9.00 mmol, 3.00 equiv.) in one lot at same temperature and allowed to stir for 30 min. The reaction mixture slowly turned into a white colored viscous paste which was acidified with acetic acid/hydrochloric acid. The mixture was extracted twice with diethyl ether (20 ml.) and the combined organic layer was concentrated to yield the crude product. Pure product was isolated by filtering the solids obtained from pouring water into the crude mixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate; In tetrahydrofuran; water; at 80℃; for 6h;Schlenk technique; Inert atmosphere; | In a 50 ml Schlenk reaction in the bottle, by adding single iodo BODIPY (50 mg, 0 . 11 mmol), 5 - fluoro -2 - formyl phenyl boronic acid (28 mg, 0 . 165 mmol), four-triphenylphosphine palladium (13 mg, 0 . 011 mmol), 20 ml tetrahydrofuran, TBAB (35 mg, 0 . 11 mmol), 3 ml 2 M Na2 CO3 Aqueous solution. The presence of nitrogen for 20 minutes, 80 C stirring reaction for 6 hours. For the chromatographic column (DCM: PE=35:65) to separate to get summer solid product 21 mg, yield 45%. The structural formula (I - 2) shown in the naphthalene ring is thick product does not symmetrical gathers the fluorine boron two-pyrrole-fluorescent dye. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; triphenylphosphine; palladium dichloride; In tetrahydrofuran; water; at 50℃; | General procedure: To a solution of the 2-formylphenylboronic acid and corresponding allyl halide (1.5 equiv.) in THF (0.2 M) in a round-bottom flask were added PdCl2/(PPh3)2 (2.5 mol %). The reaction mixture was heated to 50 C, then aq Na2CO3 (1 M, 2 equiv.) solution wasadded dropwise over a period of 1 h and the heating continued inreflux for 3-4 h. The reaction mixture was quenched with H2O and extracted with DCM (three times). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (EtOAc/PE 1:50) to afford the desired yellow product 4. |
Tags: 1256355-30-2 synthesis path| 1256355-30-2 SDS| 1256355-30-2 COA| 1256355-30-2 purity| 1256355-30-2 application| 1256355-30-2 NMR| 1256355-30-2 COA| 1256355-30-2 structure
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H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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