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CAS No. : | 352525-97-4 | MDL No. : | N/A |
Formula : | C12H11BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KALBJZHUZHGTCI-CMDGGOBGSA-N |
M.W : | 198.03 | Pubchem ID : | 55255236 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
In toluene for 3h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis-triphenylphosphine-palladium(II) chloride; water; sodium hydrogencarbonate In 1,2-dimethoxyethane at 80℃; for 19h; Inert atmosphere; | (E)-3,5-bis(4-methoxyphenyl)-4-(2-(naphthalen-4-yl)vinyl)isoxazole (3o) According to the general procedure above, iodoisoxazole 1 (180 mg, 0.442 mmol), trans- 1-napthalene-2-vinylboronic acid (131.3 mg, 0.663 mmol), NaHCO3 (111.7 mg, 1.33 mmol), DME (4 mL), H2O (3 mL), and Pd(PPh3)Cl2 (9.1 mg, 0.013 mmol) were stirred at 80oC under argon atmosphere for 19 h. The resulting dark, brown mixture was allowed to cool to room temperature at which point EtOAc (50 mL) was added. The separated organic layer was washed with H2O (15 mL), 2M NaOH (3 x 15 mL), and H2O (15 mL). The combined aqueous phase was backwashed with EtOAc (3 x 15 mL). The combined organic phase was filtered through celite, dried (MgSO4), filtered, and concentrated in vacuo to yield a yellow/orange solid (259.2 mg). Purification by silica gel column chromatography (1:3 CH2Cl2/hexanes, fractions monitored by TLC 2:1 CH2Cl2/hexanes) followed by recrystallization (CH2Cl2/hexanes) afforded 177.6 mg of pure 3o as white/brown crystals and a white/yellow solid from the filtrate (93%). mp 157-160oC. Rf= 0.3 (2:1 CH2Cl2/hexanes). 1H NMR (CDCl3, 300 MHz): δ 3.88 (s, overlapping, 6H, -OCH3), 7.01 (d, J = 16.2 Hz, 1H, vinyl-H2), 7.04 (d, overlapping, 4H, ArH-o-to-OCH3), 7.40-7.50 (t,t,t,d, overlapping, 4H, naphthalene-H3,-H7-H8 + vinyl-H1), 7.66-7.70 (m, overlapping, 2H, naphthalene-H2, -H4), 7.71 (d, J = 8.7 Hz, 2H, Ar(A)H-o-to-isoxazole), 7.78-7.83 (d,d, overlapping, 2H, naphthalene-H6,-H9), 7.84 (d, J = 9 Hz, 2H, Ar(B)H-o-to-isoxazole). 13C NMR (CDCl3, 75.4 MHz): δ 166.30 (C5-isoxazole), 162.33 (C3-isoxazole), 161.18 (Ar(A)C-ipso-to-OCH3), 160.89 (Ar(B)C-ipso-to-OCH3), 135.02 (ethenyl-C2), 133.84 (C1-napthalene), 131.36 (C5-naphthalene), 131.34 (C10-naphthalene), 130.54 (Ar(A)C-o-to-isoxazole), 129.37 (Ar(B)C-o-to-isoxazole), 128.51 (C6-naphthalene), 128.51 (C4-naphthalene), 126.31 (C8-naphthalene), 126.16 (C7-naphthalene), 125.89 (C3-naphthalene), 123.92 (C9-naphthalene), 123.42 (C2-naphthalene), 122.19 (Ar(A)C-ipso-to-isoxazole), 121.11 (Ar(B)C-ipso-to-isoxazole), 119.43 (ethenyl-C1), 114.67 (Ar(A)C-o-to-OCH3), 114.53 (Ar(B)C-o-toOCH3), 111.92 (C4-isoxazole), 55.65 (OCH3), 55.61 (OCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With benzo[1,3,2]dioxaborole; at 70℃; for 1h;Inert atmosphere; | General Procedure for Generation of Vinylboronic acids (5n-p) from Hydroboration/Hydrolysis. To a dried (120oC, overnight) 10 mL round bottom flask charged with stir bar the appropriate aryl ethynyl starting material was added and degassed under Ar for 30 min. 3.0 equivalents of catecholborane neat was added and the resulting mixture was submerged in a heated oil bath (40oC). The mixture was heated to 70oC and stirred for 1 hr. The solution was allowed to cool to room temperature at which point H2O (10 mL) was added. The resulting solution was transferred to an Erlenmeyer flask, more H2O (~50 mL) was added and the solution was mixed for 1 hr at 25 oC. The resulting solid was vacuum filtered and recrystallized with boiling H2O <strong>[1127-76-0]1-ethynylnapthalene</strong> (Aldrich) (0.43 mL, 3.0 mmol) reacted with catecholborane neat (0.95 mL, 9.0 mmol) to afford 361.6 mg as white crystals 5o [3] after recrystallization (61%). mp 128-147 oC. 1H NMR (d6-acetone, 300 MHz): delta?6.34(d, J = 18.3 Hz, 1H, vinyl-H), 7.99-7.58 (m, 3H, H7, H8, H3), 7.78 (d, J= 7.2 Hz, H2), 7.87-7.94 (m, 2H, H4, H9), 8.29 (m, 1H, H6). 13C NMR (d6-acetone, 75.4 MHz): delta? 143.56 (ethenyl-C2), 135.91 (C1), 134.09 (C5), 131.09 (C10), 128.82 (C6), 128.76 (C4), 126.44 (C7), 126.05 (C8), 125.91 (C3), 123.80 (C9), 123.68 (C2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: (E)-(2-(naphthalen-1-yl)vinyl)boronic acid With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-hydroxy-1,2-benzodioxol-3-(1H)-one In dichloromethane Stage #3: With pyridine In dichloromethane at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 1.3: 0.17 h / 20 °C 2.1: 2,2'-(1-methylethylidiene)bis(5,5-dimethyl-4,5-dihydrooxazole); tetrakis(acetonitrile)copper(I)tetrafluoroborate / 1,2-dichloro-ethane / 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | at 0 - 70℃; for 3h; Inert atmosphere; |
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