4-(Bromomethyl)benzeneboronic acid pinacol ester
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4-(Bromomethyl)benzeneboronic acid pinacol ester
structure -
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CAS No:
138500-85-3
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Formula:
C13H18BBrO2
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Chemical Name:
4-(Bromomethyl)benzeneboronic acid pinacol ester
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Synonyms:
138500-85-3;4-Bromomethylphenylboronic acid pinacol ester 95%;4-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER;4-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER;4-(Bromomethyl)benzeneboronic acid pinacol cyclic ester;4-(Bromomethyl)phenylboronic acid pinacol cyclic ester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Bromomethyl)phenylboronicacidpinacolcyclicester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(4-bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Categories:
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CAS No:
4-(Bromomethyl)benzeneboronic acid pinacol ester Basic Attributes
297
296.058319
7921808
-0
DTXSID00395701
29349990
Characteristics
18.5
2.88070
1.26±0.1 g/cm3(Predicted)
83-85°C
351.2±25.0 °C(Predicted)
166.2±23.2 °C
1.524
Keep Cold
8.44E-05mmHg at 25°C
Safety Information
III
8
3261
3
36/37/38-34
26-36/37/39-45
Xi
Harmful/Irritant/Keep Cold
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P405, P501
H314
|Danger|H314 (92.31%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 26 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-(Bromomethyl)benzeneboronic acid pinacol ester Use and Manufacturing
4-hydroxymethylphenylboronic acid, pinacol ester (1.08 g, 4.61 mmol) was dissolved in THF (20 ml) together with triphenylphosphine (2.42 g, 9.23mmol). The reaction mixture was cooled in an ice-water bath, and carbon tetrabromide (3.06 g, 9.23 mmol) was added portion wise. After stirring for 4 hours at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried by sodium sulfate. After filtration, the solvent was evaporated, and the residue was purified by flash chromatography to give the product as a white solid (1.72 g, 92percent). 1H NMR (300 MHz, CDScheme 1. Synthesis of 4-(4, 4, 5, 5-tetrarnethyl- 1, 3, 2 -dioxaboratophenyl)-methyl triphenylphosphonium bromide 4. [00120] Compound 6 (8) was prepared starting from 4, 4, 5, 5-tetramethyl-2-p-tolyl- 1 , 2>, 2- dioxaborolane 7, NBS and A1BN in carbon tetrachloride were refluxed for 12 hours. In an initial attempt 4-(4, 4, 5, 5-tetramethyl- 1 , 3, 2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 4 was isolated as a white solid in 92percent yield. The minor excess of PPh3 was removed from the product by trituration with ether 2-3 times and the product was found to be stable under normal atmospheric conditions. Subsequently, the Wittig reaction of the ylide derived from this salt using benzaldehyde (Scheme 2) was optimized.P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol), Bromosuccinimide (NBS, 9.91 g, 55.0 mmol), Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column, 4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1percent) was isolated.
Computed Properties
Molecular Weight:297.00
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:296.05832
Monoisotopic Mass:296.05832
Topological Polar Surface Area:18.5
Heavy Atom Count:17
Complexity:257
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-(Bromomethyl)benzeneboronic acid pinacol ester
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