(4-Bromophenyl)boronic acid
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(4-Bromophenyl)boronic acid
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CAS No:
5467-74-3
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Formula:
C6H6BBrO2
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Chemical Name:
(4-Bromophenyl)boronic acid
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Synonyms:
Boronic acid,B-(4-bromophenyl)-;Benzeneboronic acid,p-bromo-;Boronic acid,(4-bromophenyl)-;B-(4-Bromophenyl)boronic acid;p-Bromobenzeneboronic acid;4-Bromophenylboric acid;p-Bromophenylboric acid;(p-Bromophenyl)boronic acid;4-Bromobenzeneboronic acid;(4-Bromophenyl)boronic acid;NSC 25407
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CAS No:
(4-Bromophenyl)boronic acid Basic Attributes
200.83
200.83
226-779-9
25407
DTXSID90203129
2931900090
Characteristics
40.5
1.7±0.1 g/cm3
191 °C
315°C at 760 mmHg
144.3±28.4 °C
1.598
Soluble in methanol. Insoluble in water.
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S36-S37/39
CY8650000
Xi:Irritant
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (98.18%): 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|Aggregated GHS information provided by 55 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(4-Bromophenyl)boronic acid Use and Manufacturing
General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv), followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg ofNaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0–5 °C, followed by HCl (135 mg, 1.5 mmol, 3.0 equivalents) in MeOH (1.0 mL). This mixture was stirred 60min. H2O (10 mL) was added to reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layer was dried over Na2SO4, followed by evaporation to give the products.Dissolve Sub 1-2-1 (1) (7g, 30mmol) in anhydrous Ether, lowering the temperature ofthe reaction to -78 ° C, was added dropwise n-BuLi (2.5M in hexane) (2.1g, 22mmol)slowly, and after I, the reaction is stirred for 30 min. After the dropwise additionTriisopropyl borate (8.5g, 30mmol) lowering the temperature of the reaction back to -78 ° C. Stirring at room temperature, diluted with water and it binds the 2N HCl. Aftercompletion of reaction, ethyl acetate and water, dried over MgSO4 and the organic layerwas extracted and concentrated and to the resulting organic silicagel column andrecrystallized to give 4.46g of Sub 1-2-2 (1). (Yield: 74percent)In a 500 ml round bottom flask charged with 1, 4-dibromobenzene 30 g (127 mmol) in anhydrous tetrahydrofuran (THF) and stirred. The reaction mixture is suspended in the temperature of the flask was cooled using liquid nitrogen to -78°C and was charged with n-BuLi 2.5M (115 mmol) in 45.8 mL slowly. After raising the temperature gradually to room temperature, it stirred for 1 hour. Re-cool the temperature of the flask using liquid nitrogen to -78°C and then, triisopropylborate 48 g (58.7 mL, 254 mmol) was added quickly. Then the reaction was conducted at room temperature for 6 hours, the reaction was terminated on ice and 2 N HCl aqueous solution. Extraction with methylene chloride (MC) and then the solvent was removed, by putting into hexane, After boiling the filter to dry it with a compound 13 g (Yield = 51percent) was obtained, without further purification it was used directly in the next reaction.General procedure: In a flask containing the appropriate potassiumorganotrifluoroborate (0.5 mmol) in distilled water(1 mL) was added montmorillonite K10 (150percent m/m). Themixture was stirred for the time indicated in Scheme 1at room temperature. After this period, the mixture wasextracted with EtOAc (3 × 10 mL) and the organic phasewas washed with water (2 × 15 mL). The organic phasewas dried over anhydrous MgSO4, filtered and the solventwas removed in vacuo to yield the corresponding boronicacids 2a-o.
suzuki reaction
Computed Properties
Molecular Weight:200.83
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:199.96442
Monoisotopic Mass:199.96442
Topological Polar Surface Area:40.5
Heavy Atom Count:10
Complexity:102
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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