Isopropenylboronic acid pinacol ester
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Isopropenylboronic acid pinacol ester
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CAS No:
126726-62-3
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Formula:
C9H17BO2
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Chemical Name:
Isopropenylboronic acid pinacol ester
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Synonyms:
2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Isopropenylboronic acid pinacol ester;2-(1-Methylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropenyl boronic acid pinacol ester;4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane;2-Isopropenyl-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(Isopropenylboronic acid pinacol ester)
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CAS No:
Description
Isopropenylboronic acid pinacol ester is a versatile ester reagent used for palladium-catalyzed Suzuki-Miyaura cross-coupling processes, inverse-electron-demand Diels-Alder reaction, Simmons-Smith cyclopropanation reaction, polyene cyclization, stereoselective aldol reactions, Grubbs cross-metathesis reaction, intramolecular Suzuki-Miyaura reaction, Stereoselective cross-metathesis, dipolar cycloaddition, iodosulfonylation, asymmetric conjugate addition and intramolecular hydroacylation and pre
Characteristics
18.5
Clear, colorless to brown Liquid
0.894
157-161 °C
47-49 °C (9 mbar)
42 °C
1.432
2-8°C
Safety Information
Ⅲ
IRRITANT
UN 1993
3
10-36/37/38-43
16-26-36/37
Xi
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
H226
|Warning|H226 (97.73%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 44 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Isopropenylboronic acid pinacol ester Use and Manufacturing
Dissolve isopropenyl bromide (89.58, 0.7411101) in 75011 ^ tetrahydrofuran, dropwise add bis (diisopropylAmine) boron chloride (183 g, 0.74 mol), lithium metal (10.4 g, 1.5 ml), and 110 mL of tetrahydrofuran were added dropwise a process controlThe reaction temperature was -10 ° C to 0 ° C. After completion of the dropwise addition, the temperature was maintained for 1 hour, The reaction was then continued for 5 hours at 25 ° C.After the completion of the reaction, pinacol (988, 0.83111 01), 2, 6-di-tert-butyl-4-methylphenol (4.58) and 1201 tetrahydrofuran were added and the temperature was raised to reflux.Distillation under reduced pressure afforded the colorless transparent liquid isopropenylboronic acid pinacol ester 82.lg, yield 66percent, GC: 99.7percent2, 6-di-tert-butyl-4-methylphenol (0.45 g) was added for long-term storage.
suzuki reaction
Computed Properties
Molecular Weight:168.04
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:168.1321599
Monoisotopic Mass:168.1321599
Topological Polar Surface Area:18.5
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Isopropenylboronic acid pinacol ester
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