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CAS No. : | 1259285-61-4 | MDL No. : | MFCD16996236 |
Formula : | C13H17BF3NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RUAYESOEOHUYSN-UHFFFAOYSA-N |
M.W : | 287.09 | Pubchem ID : | 72221112 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.54 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 72.32 |
TPSA : | 44.48 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 : | Yes |
Log Kp (skin permeation) : | -5.84 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.11 |
Log Po/w (WLOGP) : | 3.75 |
Log Po/w (MLOGP) : | 2.06 |
Log Po/w (SILICOS-IT) : | 2.16 |
Consensus Log Po/w : | 2.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.67 |
Solubility : | 0.0615 mg/ml ; 0.000214 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.71 |
Solubility : | 0.0557 mg/ml ; 0.000194 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.52 |
Solubility : | 0.00869 mg/ml ; 0.0000303 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.91 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
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 |
---|---|---|
43.8% | With bis(η3-allyl-μ-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; potassium carbonate In N,N-dimethyl-formamide at 65℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 115℃; | Preparation method of compound 1a General procedure: Compound 1a-2 (3.0g, 12.5mmol), bis(pinacol)diboron (3.49 g, 13.75 mmol), potassium acetate (3.68g, 37.5mmol) and Pd(dppf)Cl2 (50 mg, 0.625 mmol) were added to the solution of 1,4-dioxane (50 ml) and the mixture was stirred at 115 °C overnight. The reaction was complete and the mixture was cooled to room temperature, filtered, extracted with water and ethyl acetate. The organic phase was separated and concentrated under reduced pressure to give the crude product which was purified by Combi-flash column chromatography to give compound 1a (1.5 g). Purity: 80%, spectrum data: MS m/z(ESI): 289[M+H]+. | |
With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 95℃; Inert atmosphere; | Sythesis of 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A- 2.1) General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+. | |
With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 95℃; Inert atmosphere; | Synthesis of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A- 2.1): General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2+ H]+. |
With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 95℃; for 16h; Inert atmosphere; | Synthesis of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A- 2.1): General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+. | |
With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 95℃; for 16h; Inert atmosphere; | Synthesis of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1):8 General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2+ H]+ | |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous potassium acetate; triethylamine at 90℃; for 16h; Inert atmosphere; | Synthesis of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1): General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under aigon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl fe/7-butyl ether (4 x 250 mL). The filtrate was washed with water (2 * 500 mL) and brine (2 * 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+. | |
Stage #1: With anhydrous potassium acetate; tricyclohexylphosphine In 1,4-dioxane for 0.166667h; Inert atmosphere; Stage #2: With palladium diacetate In 1,4-dioxane at 95℃; for 16h; Inert atmosphere; | Sythesis of 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1): General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+. | |
Stage #1: With anhydrous potassium acetate; tricyclohexylphosphine In 1,4-dioxane for 0.166667h; Inert atmosphere; Stage #2: With palladium diacetate In 1,4-dioxane at 95℃; for 16h; Inert atmosphere; | Sythesis of 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1): General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 °C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.11 g | With potassium phosphate; chloro‐(2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropyl‐1,1′‐biphenyl)‐2‐(2′‐amino‐1,1′‐biphenyl)palladium(II) In ethanol; water at 100℃; for 1.5h; | Intermediate 1.3: 4-(3-methoxvpyridin-4-vl)aniline General procedure: [00189] To a solution of (3-methoxy-4-pyridyl)boronic acid (0.7 g, 4.6 mmol, CAS: 1008506-24-8), 4-iodoaniline (1.0 g, 4.6 mmol, CAS: 540-37-4) and potassium phosphate (2.9 g, 13 mmol) in water (7 mL) and ethanol (7 mL) was added XPhos Pd G2 (1.8 g, 0.23 mmol) and the reaction heated to 80°C for 6 h. The reaction mixture was diluted with water and the crude product extracted into EtOAc. The combined organics were washed with water, brine, dried over Na2SO4 filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 50% EtOAc in heptanes) to provide the title compound (0.25 g). LCMS (Method 2): 0.54 min, 201.1 [M+H]+ |
0.11 g | With potassium phosphate; chloro‐(2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropyl‐1,1′‐biphenyl)‐2‐(2′‐amino‐1,1′‐biphenyl)palladium(II) In ethanol; water at 100℃; for 1.5h; | Intermediate 1.3: 4-(3-methoxvpyridin-4-vl)aniline General procedure: [00189] To a solution of (3-methoxy-4-pyridyl)boronic acid (0.7 g, 4.6 mmol, CAS: 1008506-24-8), 4-iodoaniline (1.0 g, 4.6 mmol, CAS: 540-37-4) and potassium phosphate (2.9 g, 13 mmol) in water (7 mL) and ethanol (7 mL) was added XPhos Pd G2 (1.8 g, 0.23 mmol) and the reaction heated to 80°C for 6 h. The reaction mixture was diluted with water and the crude product extracted into EtOAc. The combined organics were washed with water, brine, dried over Na2SO4 filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 50% EtOAc in heptanes) to provide the title compound (0.25 g). LCMS (Method 2): 0.54 min, 201.1 [M+H]+ |
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