2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No:
83622-42-8
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Formula:
C7H14BClO2
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Chemical Name:
2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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Synonyms:
(Chloromethyl)boronic acid pinacol ester (may contain 5% (Bromomethyl)boronic acid pinacol ester);2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;chloroMethylboronic acid, pinacol ester;Pinacol (Chloromethyl)boronate;2-(2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No:
2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Basic Attributes
176
176.07800
DTXSID60456125
2934999090
2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Use and Manufacturing
To the mixture of triisopropyl borate (15 ml, 65 mmol), chloroiodomethane (13 g, 72 mmol), and tetrahydrofuran (78 ml), n-butyllithium (a 1.6 M n-hexane solution, 41 ml, 65 mmol) was added dropwise at -78° C. (an outer temperature) for 20 min. and then the obtained mixture was stirred at room temperature for 2.5 hours. (Production Example 1) To a stirred solution of 2-isopropoxy-4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolane (1 1 .0 mL, 53.75 mmol) and chloroiodomethane (4.3 mL, 59.12 mmol) in anhydrous THF (100 mL), cooled to -78 °C, was added cold n-butyllithium solution (23.94 mL, 59.12 mmol) dropwise. After stirring for 30 min at this temperature, chlorotrimethylsilane (8.2 mL, 64.50 mmol) was added dropwise. After stiring for 10 min, the reaction mixture was allowed to return to room temperature and stirred for 24 h. Water (80 mL) was added and the mixture extracted with Ε∑0 (2 x 80 mL). The organic extracts were combined, washed with water (2 x 80 mL), dried over MgS04 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (Heptane/EtOAc 99:1 to 95:5).to yield 2-(chloromethyl)-4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolane (4.35 g, 24.65 mmol, 46percent yield) as a colourless oil. NMR (400 MHz, DMSO-cfe, δ): 2.99 (s, 2H), 1 .32 (s, 12H).To a mixture of triisopropyl borate (15 ml, 65 mmol), chloroiodomethane (13 g, 72 mmol) and tetrahydrofuran (78 ml) was added dropwise n-buthyllithium (1.6M n-hexane solution, 41 ml, 65 mmol) at -78°C (external temperature) over 20 minutes. Then, the mixture was stirred at room temperature for 2.5 hours. After the reaction mixture was cooled at 0°C (external temperature), to the mixture was added dropwise a 4N hydrochloric acid-ethyl acetate solution in order to neutralize at the same temperature. To the reaction mixture was added pinacol (7.7 g, 65 mmol) at the same temperature, and then, the reaction mixture was stirred at room temperature for 40 minutes. After the solvent was distilled off under reduced pressure, the resulting residue was distilled under reduced pressure (63-70°C, 11 mmHg) to obtain the title compound (9.2 g, 52 mmol, 81percent).
Computed Properties
Molecular Weight:176.45
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:176.0775375
Monoisotopic Mass:176.0775375
Topological Polar Surface Area:18.5
Heavy Atom Count:11
Complexity:143
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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