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CAS No. : | 594823-67-3 | MDL No. : | MFCD12545926 |
Formula : | C12H16BBrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FHCWGLQDAMYXJS-UHFFFAOYSA-N |
M.W : | 282.97 | Pubchem ID : | 9993953 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 70.62 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.47 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.6 |
Log Po/w (WLOGP) : | 2.75 |
Log Po/w (MLOGP) : | 2.42 |
Log Po/w (SILICOS-IT) : | 2.51 |
Consensus Log Po/w : | 2.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.07 |
Solubility : | 0.0239 mg/ml ; 0.0000844 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.67 |
Solubility : | 0.0599 mg/ml ; 0.000212 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.84 |
Solubility : | 0.00404 mg/ml ; 0.0000143 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.95 |
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 |
---|---|---|
77% | at 20℃; for 2 h; | The title compound (77percent, oil) was prepared from 3-bromophenylboronic acid and pinacol. 1H NMR (300 MHz, CDCl3): δ 1.35 (s, 12H), 7.23 (t, 1H), 7.58 (dd, 1H), 7.70 (d, 1H), 7.93 (bs, 1H). |
56.8% | at 20℃; for 6 h; Inert atmosphere | Example 14:2-(3-Bromophenyl)-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolaneTo a stirred suspension of (3-bromophenyl) boronic acid (3.0 g, 14.94 mmol) and acetonitrile (10 mL) was added pinacol (1.765 g, 14.94 mmol) and the reaction mixture was purged using argon gas. The resulting mixture was thenstirred for 6 hours at RT. After completion of the reaction, the acetonitrile was evaporated to yield the title compound.Yield: 2.4 g (56.8 percent).1HNMR (DMSO, 300 MHz): 6 7.66 (m, 4H), 1.3 (5, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: With fluoroboric acid; sodium nitrite In water at 0℃; for 1 h; Inert atmosphere; Schlenk technique Stage #2: at 22 - 25℃; for 36 h; Inert atmosphere; Schlenk technique; Sealed tube |
General procedure: An arylamine (50 mmol) was dissolved in 50percent hydrofluoroboric acid(17 mL) and water (20 mL). After cooling the reaction mixture to 0 °C, a solution of sodium nitrite (3.4 g in 7.5 mL water) was added dropwise to the reaction system (over 5 min). The resulting mixture was stirred for 1h and the precipitate was collected by filtration. It was redissolved in the minimum amount of acetone and then diethyl ether was added to precipitate the aryl diazonium tetrafluoroborate. The product was filtered, washed with diethyl ether and dried under reduced pressure. Borylation of aryldiazonium salts; general procedure The aryldiazonium salt (0.5 mmol) and (Bpin)2 (0.75 mmol) were added to an oven-dried Schlenk tube. The tube was evacuated and backfilled with argon (three times). CH3OH (0.8 mL) was added to this Schlenk tube. The tube was sealed and the mixture was stirred at room temperature (22–25 °C) for 36 h. After evaporation of the solvent, the residue was purified by column chromatography to afford the product.The arylboronates were purified by chromatography on a silica column eluting with petroleum ether (boiling range 60–90 °C) or a petroleumether/ethyl acetate mixture (ca. 60:1) by volume giving Rf values for the boronates of ca. 0.2–0.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2 h; Inert atmosphere; Schlenk technique | General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 °C and stirred for 2 h under argon. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: With ferrocene In acetonitrile at 20℃; for 2.5 h; Stage #2: With methanol In acetonitrile at 0 - 20℃; for 1 h; Stage #3: at 20℃; for 4 h; |
Example 3: General procedure D for the synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane, catalysed by ferrocene (1percent), followed by methanolysis and transesterification In a dried tube reactor under argon as described in example 2, the arenediazonium salt (1 mmol) and the ferrocene (ΙΟμιηοΙ, 1.8mg) were dissolved in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol, 226mg) was then added to the solution and the mixture was stirred for 2h30 at room temperature. The reaction mixture was quenched by a slow addition of anhydrous MeOH at 0°C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol was added in Et20 (2mL), the mixture was stirred 4h at room temperature. The crude mixture was washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer were separated, dried over Na2S04, filtered and concentrated to dryness. The resulted oil was dissolved with CH2C12 and filtered of a pad of silica gel, eluting with CH2C12 to afford the corresponding boronate. Example 24: synthesis of 2-(3-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [CAS 594823-67-3], compound VIA21. 204 mg of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane were obtained following the general procedure D according to example 3, using 271 mg of 3-bromobenzenediazonium tetrafluoroborate as a pale yellow oil, with an isolated yield of 72percent. 1H NMR (300 MHz, CDC13) δ 7.75 (d, J = 7.3 Hz, 1H) 7.62 (ddd, J = 8.0, 2.0, 1.1 Hz, 1H) 7.27 (d, J = 7.7 Hz, 1H) 1.38 (s, 12H) nB NMR (100 MHz, CDC13) δ 30.65 13C NMR (75 MHz, CDC13) δ 137.63, 134.32, 133.23, 129.63, 122.60, 84.31, 25.01. MS (EI) tR= 9.03 min; m/z: 283 (Μ+', 100percent) |
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