9,9-Dimethyl-9H-fluoren-2-yl-boronic acid
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9,9-Dimethyl-9H-fluoren-2-yl-boronic acid
structure -
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CAS No:
333432-28-3
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Formula:
C15H15BO2
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Chemical Name:
9,9-Dimethyl-9H-fluoren-2-yl-boronic acid
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Synonyms:
9,9-dimethyl-9h-fluoren-2-yl-boronic acid;BORONIC ACID,(9,9-DIMETHYL-9H-FLUOREN-2YL)-;Boronic acid, (9,9-dimethyl-9H-Fluoren-2-ylbutyl);9,9-DIMETHYL-9H-FLUOROEN-2-YL BORONIC ACID;9,9-DIMETHYL-2-FLUORENEBORONIC ACID;2-Bromo-9,9-dimethyl-9H-fluorene;9,9-dimethyl-9H-fluorene-2yl boronic acid;9,9-Dimethyl-9H-fluoren-2-yl-2-boronic acid
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CAS No:
9,9-Dimethyl-9H-fluoren-2-yl-boronic acid Basic Attributes
238.09
238.116516
1533716-785-6
DTXSID30625104
2931900090
Safety Information
36
26
Xi
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P501
H302
|Warning|H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
9,9-Dimethyl-9H-fluoren-2-yl-boronic acid Use and Manufacturing
2-bromo-9, 9-dimethyl--9H-Fluorene 100 g(366 mmol) under a stream of nitrogen and dissolved in 1000 ml oftetrahydrofuran and stirred at -78 with 1.6 Mn-butyllithium 275 ml (439 mmol) was added dropwise and when the addition wascomplete while maintaining the -78 the mixture wasstirred for one hour. Then trimethylborate 49.5 g (476 mmol) was added dropwiseslowly by raising the mixture to room temperature and stirred for one hour. After the reaction was terminated 1 M hydrochloricacid of aqueous solution was added dropwise and the mixture was stirred for 30minutes at room temperature. The organic layer was extracted and concentratedunder reduced pressure and recrystallized from methylene chloride and hexane toobtain a compound 70g represented by. (Yield 80percent)These compounds were obtained following an essentially similar procedure. An illustrative example is provided for 11: Compound 8: (13.66 g, 0.05 mol) was dissolved in anhydrous THF (60 mL) in a three-necked round-bottom flask fitted with a magnetic stirrer, a condenser, a NAt -78°C in a nitrogen atmosphere, 9, 9-dimethyl-2-bromofluorene (30g, 109.8mmol) was dissolved in THF 500mL, and 2.5M n-BuLi(2.5M in hexane, 20.7mL, 142.7mmol) was added. This mixture was stirred for 1 hour. B(OMe)Preparation of Structural Formula 14D; 2-bromo-9, 9-dimethylfluorene (15 g, 54.9 mmol) was dissolved in 150 ml of tetrahydrofurane anhydride, and cooled to -78C, and 2.5 M n-butyl lithium (24.2 ml, 60.4 mmol) was slowly added thereto, and agitated for 1 hour. Trimethyl borate (9.2 ml, 82.4 mmol) was added to the reaction solution, and agitated for 30 min, 6N HCl 50 ml was added thereto, the temperature was increased to normal temperature, and it was agitated for 1 hour. The organic layer was extracted, concentrated, and recrystallized with n-hexane to obtain the Structural Formula 14D (10 g, yield 77percent). MS: [M+ H]Synthesis Example: Synthesis of Compound 29 [Show Image] Synthesis of Intermediate 14 27.3 g (100.0 mmol) of 2-bromo-9, 9-dimethylfluorene was dissolved in 200 mL of THF, the solution was cooled to -78°C, and 44 mL (2.5 M in hexane, 110 mmol) of butyl lithium was slowly dropwise added to the solution in a nitrogen atmosphere. The reaction temperature was maintained at -78°C for 30 minutes, raised to -30°C and cooled again to - 78°C. Then, 16.8 mL (150 mmol) of trimethylborate was slowly dropwise added to the reaction product, and the temperature was raised to room temperature and maintained for 2 hours. 50 mL of 1 N HCl solution was slowly dropwise added to the reaction mixture and maintained for 30 minutes. 100 mL of water was further added to the reaction mixture, and the reaction mixture was subjected to extraction twice with 200 ml of ethylacetate. An organic layer was collected and dried, followed by filtration and concentration. The residue was separated by column chromatography to obtain 16.4 g (yield: 69percent) of white solid Intermediate 14.In nitrogen gas, clean and dry 1000ml three-neck bottle, add 6a, triisopropyl borate and THF in proportion, cool down to-100°C, add butyllithium dropwise, add complete, keep warm for 2 hours, acidify with hydrochloric acid, wash with water, and remove the solvent , toluene beating, got 6b;HPLC: 99.9percent, yield: 70percent;
Computed Properties
Molecular Weight:238.09
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:238.1165099
Monoisotopic Mass:238.1165099
Topological Polar Surface Area:40.5
Heavy Atom Count:18
Complexity:316
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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9,9-Dimethyl-9H-fluoren-2-yl-boronic acid
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