| Identification | More | [Name]
TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID | [CAS]
154230-29-2 | [Synonyms]
RARECHEM AL BA 0169
(4-Chlorostyryl)boronic acid
(E)-(4-Chlorostyryl)boronic acid
TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACI
TRANS-2-(4-CHLORPHENYL)VINYLBORONIC ACID
TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID
trans-2-(4-Chlorophenyl)ethenylboronic acid
[(Z)-2-(4-chlorophenyl)ethenyl]boronic acid
Boronic acid, [(1E)-2-(4-chlorophenyl)ethenyl]-
Boronic acid, B-[(1E)-2-(4-chlorophenyl)ethenyl]- | [Molecular Formula]
C8H8BClO2 | [MDL Number]
MFCD02093767 | [Molecular Weight]
182.41 | [MOL File]
154230-29-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
165 °C (dec.)(lit.) | [Boiling point ]
356.7±44.0 °C(Predicted) | [density ]
1.277±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Crystalline Powder | [pka]
9.55±0.43(Predicted) | [color ]
White to off-white | [CAS DataBase Reference]
154230-29-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Reactant involved in:
- Synthesis of biarylketones and phthalides
- Trifluoromethylation
- Asymmetrical Michael addition for preparation of chromanes
- Cobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds
- 1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydes
- Petasis reactions
| [Uses]
Reactant involved in:• ;Synthesis of biarylketones and phthalides1• ;Trifluoromethylation2• ;Asymmetrical Michael addition for preparation of chromanes3• ;Cobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds4• ;1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydes5• ;Petasis reactions6 | [Synthesis]
General procedure for the synthesis of (E)-(4-chlorophenylvinyl)boronic acid from 4-chlorophenylacetylene and catecholborane: 1-chloro-4-ethynylbenzene (0.50 g, 3.66 mmol, 1.00 eq.) and catecholborane (0.47 mL, 4.39 mmol, 1.20 eq.) were dissolved in tetrahydrofuran (THF, 1.4 mL) and the mixture was refluxed for for 18 hours. After completion of the reaction, the solvent was removed by evaporation and water (1 mL) was added. The suspension was stirred vigorously for 4 h at room temperature. The solid was collected by filtration and recrystallized from water. It was filtered again to give (E)-(4-chlorophenylvinyl)boronic acid (652.9 mg, 3.62 mmol, 99% yield) and dried under vacuum. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (101 MHz, DMSO) with the following data: 1H NMR (DMSO-d6) δ 7.83 (s, 2H), 7.50 (d, J = 8.4 Hz, 2H), 7.45-7.39 (m, 2H), 7.24 (d, J = 18.4 Hz. 1H), 6.14 (d, J = 18.3 Hz, 1H); 13C NMR (DMSO) δ 145.7, 144.8, 137.0, 133.3, 129.2 (2C), 128.7 (2C). | [References]
[1] Patent: WO2016/198836, 2016, A1. Location in patent: Paragraph 00142 |
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