6-BROMO-2,3-DIHYDRO-BENZOFURAN
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6-BROMO-2,3-DIHYDRO-BENZOFURAN
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CAS No:
189035-22-1
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Formula:
C8H7BrO
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Chemical Name:
6-BROMO-2,3-DIHYDRO-BENZOFURAN
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Synonyms:
6-bromo-2,3-dihydrobenzofuran;6-BROMO-2,3-DIHYDRO-1-BENZOFURAN;Benzofuran, 6-bromo-2,3-dihydro-;6-BROMO-2,3-DIHYDROBENZO[B]FURAN;MFCD08704305;6-BROMO-2,3-DIHYDRO-BENZOFURAN;6-BROMOCOUMARAN;SCHEMBL267355;CTK4E0002;DTXSID60460146
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CAS No:
Characteristics
9.2
2.8
1.582±0.06 g/cm3(Predicted)
239.8±29.0 °C(Predicted)
94.9ºC
1.601
H2O: Very slightly soluble (0.22 g/L) (25 ºC)
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, 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.
6-BROMO-2,3-DIHYDRO-BENZOFURAN Use and Manufacturing
nBuLi (2.5 M in hexane, 5.13 ml_, 12.84 mmol) was added to a -78°C cooled solution of 1 , 4-dibromo-2-(2-bronnoethoxy)benzene (3.84 g, 10.70 mmol) in THF (100 ml_). The reaction mixture was stirred at low temperature for 4 h. It was poured into HTo a solution of 1, 4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene / tetrahydrofuran (28 mL, 2:5) at -78°C under NTo a solution of 1, 4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene/ tetrahydrofuran (28 mL, 2:5) at −78° C. under N2 was added n-butyllithium (2.5 mL, 6.1 mmol). The mixture was stirred at −78° C. for 1 h, and quenched by acetic acid. Water was added, and the organic layer was seperated, dried, and concentrated under vacuum to give the title compound (1.00 g, 85percent). 1H NMR (CDCl3) δ7.03 (1H, d, J=8, 0 Hz), 6.91-6.93 (2H, m), 4.58 (2H, t, J=4.8 Hz), 3.15 (2H, t, J=4.8 Hz).1.6 M n-Butyllithium/hexane solution (21.84 mL, 34.94 mmol) was slowly added to a solution of 1, 4-dibromo-2-(2-bromoethoxy)benzene (10.45 g, 29.12 mmol) in THF (200 mL) at-78°C under argon gas atmosphere. The reaction mixture was stirred at -78°C for 30 min, and then at 0°C for 2 hr. The reaction mixture was added to ice water, and 2N hydrochloric acid was added thereto until the pH of the mixture became 3. Then, the mixture was extracted three times with a mixed solvent of ethyl acetate/hexane (3:1). The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 2→8percent ethyl acetate/hexane) to give 6-bromo-2, 3-dihydrobenzofuran (4.57 g, 22.96 mmol, 79percent) as a white solid.To a solution of 1, 4-dibromo-2-(2-bromoethoxy)benzene (22.3 g, 62.2 mmol) in THF (180 mL) was added 1.57 M n-BuLi in hexanes (40 mL, 62.8 mmol) under Ar at -76 °C. 2-(2, 5-dibromophenoxy)ethanol (4.65 g, 15.7 mmol) was dissolved in toluene (33 mL) with stirring under N
Computed Properties
Molecular Weight:199.04
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Exact Mass:197.96803
Monoisotopic Mass:197.96803
Topological Polar Surface Area:9.2
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
