4-(Methoxycarbonyl)phenylboronic acid
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4-(Methoxycarbonyl)phenylboronic acid
structure -
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CAS No:
99768-12-4
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Formula:
C8H9BO4
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Chemical Name:
4-(Methoxycarbonyl)phenylboronic acid
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Synonyms:
Benzoic acid,4-borono-,1-methyl ester;Benzoic acid,p-borono-,methyl ester;4-Carbomethoxybenzeneboronic acid;4-Methoxycarbonylbenzeneboronic acid;(4-Carbomethoxyphenyl)boronic acid;p-(Methoxycarbonyl)boronic acid;Methyl p-boronobenzoate;p-(Methoxycarbonyl)phenylboronic acid;4-(Methoxycarbonyl)phenylboronic acid;Methyl 4-boronobenzoate;Methyl 4-carboxyphenylboronic acid;4-Dihydroxyborylbenzoic acid methyl ester;4-Methoxycarbonylphenylboric acid;1373752-82-9
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CAS No:
4-(Methoxycarbonyl)phenylboronic acid Basic Attributes
179.97
179.97
1806241-263-5
DTXSID40370259
2931900090
Characteristics
66.8
1.3±0.1 g/cm3
230-233 °C @ Solvent: Water
345.8°C at 760 mmHg
162.9±28.4 °C
1.533
soluble in methanol.
0-6°C
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
37/39-26
Xi
|Warning|H302 (21.43%): 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, P403+P233, P405, and P501|Aggregated GHS information provided by 14 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-(Methoxycarbonyl)phenylboronic acid Use and Manufacturing
In 500mL three-necked flask, Methyl 4-bromobenzoate (20.2 g, 77.2 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.9 g, 100.3 mmol) was added, Cool to -78 ° C, N-Butyllithium (6.8 g, 96.5 mmol) was added dropwise, Maintain the reaction temperature 0.5h.The reaction is completed, Saturated aqueous ammonium chloride solution was quenched, 1mol / L hydrochloric acid to adjust the pH to 1, Ethyl acetate (100.0 mL × 3), the organic phases were combined, Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane, The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.3g, a yield of 95.5percent.In 500mL three-necked flask, Methyl 4-iodobenzoate (20.1 g, 76.7 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.0 g, 95.9 mmol) was added, Cool to -78 ° C, N-Butyllithium (6.1 g, 95.9 mmol) was added dropwise, Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution, 1mol / L hydrochloric acid to adjust the pH to 1, Ethyl acetate (100.0 mL x 3)The combined organic phase, Saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, The residue was beaten with n-hexane, and filtered to obtain 13.1 g of 4-methoxycarbonylphenylboronic acid, Yield 94.8percent.In 500mL three-necked flask, Methyl 4-iodobenzoate (20.4 g, 77.8 mmol) was dissolved in dry THF (200.0 mL)Tri-n-butyl borate (21.5 g, 93.4 mmol) was added, Cool to -78 ° C, N-Butyllithium (5.5 g, 85.6 mmol) was added dropwise, Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution, 1mol / L hydrochloric acid to adjust the pH to 1, Ethyl acetate (100.0 mL x 3)The combined organic phases were washed with saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, The residue was beaten with n-hexane, Filtered to give 4-methoxycarbonyl phenylboronic acid 12.7g, the yield was 91.0percent.In 500mL three-necked flask, Methyl 4-iodobenzoate (20.3 g, 77.4 mmol) was dissolved in dry THF (200.0 mL)Trimethyl borate (16.1 g, 154.8 mmol) was added, The temperature was lowered to -78 ° C and n-butyllithium (7.4 g, 116.1 mmol) was added dropwise.Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution, 1mol / L hydrochloric acid to adjust the pH to 1, Ethyl acetate (100.0 mL × 3), the organic phases were combined, Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane, The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.2g, a yield of 94.5percent.
suzuki reaction
Computed Properties
Molecular Weight:179.97
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:180.0593889
Monoisotopic Mass:180.0593889
Topological Polar Surface Area:66.8
Heavy Atom Count:13
Complexity:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-(Methoxycarbonyl)phenylboronic acid
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