Cyclohexylboronic acid pinacol ester
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Cyclohexylboronic acid pinacol ester
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CAS No:
87100-15-0
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Formula:
C12H23BO2
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Chemical Name:
Cyclohexylboronic acid pinacol ester
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Synonyms:
CYCLOHEXYLBORONIC ACID ACID PINACOL ESTER;2-Cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;REF DUPL: Cyclohexylboronic acid pinacol ester;Cyclohexylboronic acid pinacol este;(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane;1,3,2-Dioxaborolane, 2-cyclohexyl-4,4,5,5-tetraMethyl-;Cyclohexane acid pinacol ester;CYCLOHEXYLBORONIC ACID PINACOL ESTER
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CAS No:
Safety Information
IRRITANT
36/37/38
26-36/37/39
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Cyclohexylboronic acid pinacol ester Use and Manufacturing
General procedure: A mixture of boronic acid (1.0 equiv), pinacol (1.0 equiv) and anhydrous MgSO4 (4.0 equiv) in Et2O (0.5 M) was stirred at r.t. for 16 h. The reaction mixture was filtered and the solvent removed in vacuo. The crude material was purified by distillation or flash column chromatography to give the pure boronic ester.Magnesium chippings (3.8 g, 156 mmol, 1.0 eq.) were added to a dried flaskunder argon atmosphere and suspended with dry Et2O (20 mL). A small amount(10 mL) of a solution of cyclohexyl bromide (19.2 mL, 156 mmol, 1.0 eq.) in dryEt2O (200 mL) was added to the magnesium and the activation of the Grignardformation was accelerated by addition of an iodine crystal and heating.Afterwards, the rest of the solution of cyclohexyl bromide in (19.2 mL, 156 mmol, 1.0 eq.) in Et2O(200 mL) was added dropwise over 2 h. The reaction mixture was heated to reflux for 1 h and thenstirred for 17 h.[*a] The reaction mixture was transferred via decantation under a constant flow of argoninto a well dried addition funnel and added dropwise to a solution of trimethyl borate (17.7 mL, 159mmol, 1.02 eq) in Et2O (450 mL) at -78 °C for 2 h. The reaction mixture was then quenched bydropwise addition of HCl (10 wt.percent, 200 mL) and extracted with Et2O (2 x 100 mL), dried over MgSO4and the solvent was removed in vacuo to give c-hex-B(OH)2 as a white solid (Crude: 15.96 g, 125mmol, 80percent). The solid residue was used without further purification and dissolved in dry Et2O(150 mL). Pinacol (17.9 g, 151 mmol, 1.2 eq.) was added in portions at 0 °C and then the reactionmixture was stirred for 72 h.[*b] As a desiccant MgSO4 (5 g) was added to the reaction mixture andstirring was continued for 48 h.[*c] Then the residue was filtered over celite and washed with Et2O (2 x25 mL) and the solvent was removed in vacuo to give a colorless oil. The residue was purified bydistillation (b.p. 65-80 °C, at 4.7-5.0 mbar). The product, c-hex-B(pin) (6) was obtained as a colorlessoil (14.8 g, 70.4 mmol, 56percent).General procedure: Scheme 17 illustrates hydrogenation of a substituted (e.g., trifluoromethyl- or methoxycarbonyl-substituted) or unsubstituted spGeneral procedure: In air, [Rh(COD)Cl]Chlorocyclohexane 5 (3.0 mmol, 0.36 g), (CF
Computed Properties
Molecular Weight:210.12
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:210.1791101
Monoisotopic Mass:210.1791101
Topological Polar Surface Area:18.5
Heavy Atom Count:15
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Cyclohexylboronic acid pinacol ester
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