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CAS No. : | 1257213-52-7 | MDL No. : | MFCD18383419 |
Formula : | C18H25BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZYSWTQGHMDIKPH-UHFFFAOYSA-N |
M.W : | 316.20 | Pubchem ID : | 53217182 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.61 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 90.97 |
TPSA : | 44.76 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) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.41 |
Log Po/w (WLOGP) : | 2.52 |
Log Po/w (MLOGP) : | 2.26 |
Log Po/w (SILICOS-IT) : | 3.15 |
Consensus Log Po/w : | 2.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.81 |
Solubility : | 0.0488 mg/ml ; 0.000154 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.03 |
Solubility : | 0.0295 mg/ml ; 0.0000934 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.28 |
Solubility : | 0.00167 mg/ml ; 0.00000528 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.27 |
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 |
---|---|---|
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | l-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3.6g, 13.4mmol), bis(pinacolato)diboron (3.37g, 16. lmmol), and potassium acetate (2.8g, 29mmol) were combined in 1,4-dioxane (3OmL). The solution was purged with N2 for 10 minutes, and then (l,l'-bis(diphenylphosphino)ferrocene)- dichloropalladium(II) (0.5Og, 0.65mmol) was added and the reaction was heated to 8O0C for 2 hours. Aqueous work-up, followed by silica gel chromatography (0-30% EtOAc in hexanes), gave the title compound. | |
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | Step 9: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3.6 g, 13.4 mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2 atmosphere. The solution was purged with N2 (g) for 10 minutes, and then (1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound. | |
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | Step 4: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3 g, 13.mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2. The solution was purged with N2 for 10 minutes, then (1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound. |
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | l-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3 g, 13. mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2. The solution was purged with 2 for 10 minutes, then (l, l '-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound. | |
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | Step 4: l-[4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester: l-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3.6g, 13.4mmol), bis(pinacolato)diboron (3.37g, 16.1mmol), and potassium acetate (2.8g, 29mmol) were combined in 1,4- dioxane (30mL). The solution was purged with N2 for 10 minutes, and then (1,1'- bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50g, 0.65mmol) was added and the reaction was heated to 80C for 2 hours. Aqueous work-up, followed by silica gel chromatography (0-30% EtOAc in hexanes), gave the title compound. | |
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere; | Step 9: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3.6 g, 13.4 mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2 atmosphere. The solution was purged with N2 (g) for 10 minutes, and then (1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere; | Step 10: 1-[4'-(4-tert-Butoxycarbonylamino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid tert-butyl ester (2.0 g, 5.6 mmol), <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong> (1.78 g, 5.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol), and sodium bicarbonate (1.4 g, 16.8 mmol) were combined in DME (30 mL) and H2O (10 mL), and the mixture was purged with N2 (g). The reaction was stirred at 80 C. overnight, and after aqueous workup, the crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound. | |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; ethyl acetate; at 80℃;Inert atmosphere; | Step 5: 1-[4'-(4-tert-Butoxycarbonylamino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid tert-butyl ester (2.0 g, 5.6 mmol), <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong> (1.78 g, 5.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol), and sodium bicarbonate (1.4 g, 16.8 mmol) were combined in DME (30 mL) and H2O (10 mL) and the mixture was purged with N2. The reaction was stirred at 80 C. overnight, and after aqueous workup the crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound. | |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere; | Step 10 1-[4'-(4-tert-Butoxycarbonylamino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid tert-butyl ester (2.0 g, 5.6 mmol), <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong> (1.78 g, 5.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol), and sodium bicarbonate (1.4 g, 16.8 mmol) were combined in DME (30 mL) and H2O (10 mL), and the mixture was purged with N2 (g). The reaction was stirred at 80 C. overnight, and after aqueous workup, the crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 60 - 80℃;Inert atmosphere; | Step 1: 1-[4'-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester Prepared according to the procedure described in Example 4, using [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol and <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong>.Example 4 Suzuki Coupling RactionA 4-substituted-5-(4-bromo-phenyl)-3-methyl-isoxazole (1 equivalent), <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong> (1.2-2.0 equivalents), tetrakis(triphenylphosphine)palladium(0) (0.05-0.15 equivalents), and sodium bicarbonate (2.5 equivalents) were combined in 3:1 DME :H2O, and the mixture was purged with N2 (g). The reaction was stirred at 60-80 C. for at least 1 hour to overnight and then cooled and concentrated. The crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 85℃;Inert atmosphere; | Step 1: 5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.5 g, 1.88 mmol) was mixed with 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester (0.72 g, 2.07 mmol) and sodium bicarbonate (0.553 g, 6.58 mmol) in DME (5 mL) and H2O (2.5 mL). The reaction was purged with N2 (g) then bis(triphenylphosphine)palladium(II) dichloride (0.066 g, 0.094 mmol) was added and the reaction was heated to 85 C. overnight. After cooling to room temperature the reaction was submitted to standard aqueous workup the purified by silica gel chromatograph (0-20% EtOAc in hexanes) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Product distribution / selectivity; | Step 3: 1-{4'-[3-Methyl-4-(2-oxo-4-phenyl-butyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester Prepared according to the procedure described in Example 3, Step 5, using 1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-4-phenyl-butan-2-one and <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 80℃; for 4.0h;Inert atmosphere; | l-[4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]- cyclopropanecarboxylic acid ethyl ester (2 g, 6.33 mmol), l-bromo-4-iodo-benzene (1.97 g, 6.96 mmol), and sodium bicarbonate (1.59 g, 18.98 mmol) were dissolved inDME:H20 (2: 1). The solution was sparged with 2 (g) for ten minutes then (1, 1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.52 g, 0.063 mmol) was added and 2 (g) was introduced for an additional 5 minutes. The reaction was heated to 80 C for 4 hours then cooled and submitted to EtOAc/H20 workup. The crude material was purified on silica gel (0-70% EtOAc in hexanes) to provide the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 6.0h;Inert atmosphere; | To a stirred mixture of compound XL-5 (1 g, 3.4 mmol), compound XL-6 (1.06 g, 3.4 mmol) and Na2C03 (1.08 g, 10.2 mmol) in dimethoxyethane (15 mL) and H20 (5 mL) was added Pd(dppf)Cl2 (124mg, 0.17mmol). The reaction mixture was flushed with N2 and heated to 80 C for 6 hrs. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography (PE:EA = 10: 1) to give compound XL-7 (850 mg, yield 65%). MS (ESI) m/z (M+H)+ 405.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 1.5h;Inert atmosphere; | A solution of 1.2 g (3.8 mmol) of 4-bromo-1-iodo-2-methoxybenzene synthesized in analogy to Reference Example 5, 1.1 g (3.5 mmol) of <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester</strong> (synthesized according to a process described in WO 12/078593) and 1.1 g (10 mmol) of sodium carbonate in 1,4-dioxane (15 ml)-water (10 ml) was degassed and subject to nitrogen. Then, 0.10 g (0.12 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride methylene chloride adduct was added, and the mixture was heated and stirred under a nitrogen atmosphere at 80C for 1.5 hours. After completion of the reaction, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, subsequently dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 94:6 to 75:25 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.72 g (1.9 mmol, yield 55%) of the title compound as a white solid. Mass spectrum (EI, m/z): 374 [M]+. 1 H-NMR spectrum (400 MHz, CDCl3) delta : 7.45-7.41 (2H, m), 7.39-7.35 (2H, m), 7.19 (1H, d, J = 8.0 Hz), 7.15 (1H, dd, J = 8.0, 1.8 Hz), 7.10 (1H, d, J = 1.8 Hz), 4.12 (2H, q, J = 7.1 Hz), 3.81 (3H, s), 1.61 (2H, dd, J = 7.0, 4.0 Hz), 1.22 (2H, dd, J = 7.0, 4.0 Hz), 1.19 (3H, t, J = 7.1 Hz). |
55% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 1.5h;Inert atmosphere; | (Reference Example 4) 1-(4'-bromo-2'-methoxy-[1,1'-biphenyl]-4-yl)cyclopropanecarboxylic acid ethyl ester A 1,4-dioxane (15 ml)-water (10 ml) solution of 1.2 g (3.8 mmol) of 4-bromo-1-iodo-2-methoxybenzene synthesized in analogy to Reference Example 3, 1.1 g (3.5 mmol) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester (synthesized in accordance with the process described in ) and 1.1 g (10 mmol) of sodium carbonate was degassed and was purged with nitrogen. Next, 0.10 g (0.12 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride methylene chloride adduct was added. The mixture was stirred in a nitrogen atmosphere for 1.5 hours while performing heating at 80C. After the completion of the reaction, water was added to the reaction mixture liquid, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent: hexane:ethyl acetate = 94:6 to 75:25 (V/V)), and the fraction containing the target compound was concentrated under reduced pressure and was dried by vacuum heating to give the title compound weighing 0.72 g (1.9 mmol, yield 55%) as a white solid. Mass spectrum (EI, m/z): 374 [M]+. 1H-NMR spectrum (400MHz, CDCl3) delta: 7.45-7.41 (2H, m), 7.39-7.35 (2H, m), 7.19 (1H, d, J = 8.0 Hz), 7.15 (1H, dd, J = 8.0, 1.8 Hz), 7.10 (1H, d, J = 1.8 Hz), 4.12 (2H, q, J = 7.1 Hz), 3.81 (3H, s), 1.61 (2H, dd, J = 7.0, 4.0 Hz), 1.22 (2H, dd, J = 7.0, 4.0 Hz), 1.19 (3H, t, J = 7.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 2.0h;Inert atmosphere; | A solution of 1.5 g (2.9 mmol (purity 74% by weight)) of 5-bromo-2-iodobenzoic acid tert-butyl ester synthesized in Reference Example 6, 0.85 g (2.7 mmol) of <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester</strong> (synthesized according to a process described in WO 12/078593) and sodium carbonate (0.85 g, 8.0 mmol) in 1,4-dioxane (10 ml)-water (5 ml) was degassed and subjected to nitrogen replacement. Then, 0.050 g (0.061 mmol) of [,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride methylene chloride adduct was added, and the mixture was heated and stirred under a nitrogen atmosphere at 80C for 2 hours. After completion of the reaction, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, subsequently dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 94:6 to 75:25 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.89 g (2.0 mmol, yield 69%) of the title compound as a white solid. Mass spectrum (EI, m/z): 444 [M]+. 1 H-NMR spectrum (400 MHz, CDCl3) delta : 7.89 (1H, d, J = 2.1 Hz), 7.59 (1H, dd, J = 8.3, 2.1 Hz), 7.38-7.34 (2H, m), 7.24-7.18 (3H, m), 4.11 (2H, q, J = 7.1 Hz), 1.63 (2H, dd, J = 7.0, 4.0 Hz), 1.24 (9H, s), 1.19 (2H, dd, J = 7.0, 4.0 Hz), 1.18 (3H, t, J = 7.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; water; toluene; at 100℃; for 11.5h;Inert atmosphere; | A solution of 2.17 g (20.5 mmol) of sodium carbonate in toluene (20 ml)-water (20 ml)-ethanol (5 ml) was degassed by bubbling with argon gas, and then 4.28 g (15.1 mmol) of 5-bromo-2-iodopyridine (Aldrich), 4.33 g (13.7 mmol) of <strong>[1257213-52-7]1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester</strong> (synthesized according to a process described in WO 12/078593) and 0.56 g (0.69 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride methylene chloride adduct were added. The pressure was reduced once, the atmosphere was replaced with argon, and the mixture was heated and stirred at 100C for 11.5 hours. After completion of the reaction, the reaction mixture was cooled, and ethyl acetate and water were added to separate the layers. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 99:1 to 90:10 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 2.58 g (7.45 mmol, yield 54%) of the title compound as a white solid. Mass spectrum (EI, m/z): 345 [M]+. 1 H-NMR spectrum (400 MHz, DMSO-d6) delta : 8.78 (1H, dd, J = 2.4, 0.5 Hz), 8.12 (1H, dd, J = 8.5, 2.4 Hz), 8.04-7.98 (2H, m), 7.95 (1H, dd, J = 8.6, 0.6 Hz), 7.47-7.42 (2H, m), 4.04 (2H, q, J = 7.1 Hz), 1.52 (2H, dd, J = 6.9, 4.0 Hz), 1.24 (2H, dd, J = 7.1, 4.1 Hz), 1.10 (3H, t, J = 7.1 Hz). |
Tags: 1257213-52-7 synthesis path| 1257213-52-7 SDS| 1257213-52-7 COA| 1257213-52-7 purity| 1257213-52-7 application| 1257213-52-7 NMR| 1257213-52-7 COA| 1257213-52-7 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
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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