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[ CAS No. 4790-81-2 ]

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Chemical Structure| 4790-81-2
Chemical Structure| 4790-81-2
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Product Details of [ 4790-81-2 ]

CAS No. :4790-81-2 MDL No. :MFCD03788248
Formula : C8H6O2 Boiling Point : 247.1±13.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :134.13 g/mol Pubchem ID :78515
Synonyms :

Safety of [ 4790-81-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4790-81-2 ]

  • Downstream synthetic route of [ 4790-81-2 ]

[ 4790-81-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 7168-85-6 ]
  • [ 4790-81-2 ]
YieldReaction ConditionsOperation in experiment
55% With boron tribromide; In dichloromethane; at 0 - 20℃; for 4h; To a round bottom flask containing <strong>[7168-85-6]7-methoxybenzofuran</strong> (2.45 g, 16.5 mmol) and anhydrous DCM (25 mL) was carefully added a solution of boron tribromide in DCM (1 M, 33 mL) at 0 C. The reaction was allowed to warm to rt and stir at rt for 4 h. The reaction was quenched with water (20 mL), extracted with Et^O, concentrated to dryness, and purified by flash column chromatography to yield the title compound (1.23 g, 55% yield) as a light-brown oil. MS (ESI): mass calcd. for C8H602, 134.0.1; m/z found, 135.1 [M+H]+.
55% With boron tribromide; In dichloromethane; at 0 - 20℃; for 4h; To a round bottom flask containing <strong>[7168-85-6]7-methoxybenzofuran</strong> (2.45 g, 16.5 mmol) and anhydrous DCM (25 mL) was carefully added a solution of boron tribromide in DCM (1 M, 33 mL) at 0 . The reaction was allowed to warm to rt and stir at rt for 4 h. The reaction was quenched with water (20 mL), extracted with Et 2O, concentrated to dryness, and purified by flash column chromatography to yield the title compound (1.23 g, 55% yield) as a light-brown oil. MS (ESI) : mass calcd. for C 8H 6O 2, 134.0.1 m/z found, 135.1 [M+H] +.
52% With boron tribromide; In dichloromethane; water; at -78 - 20℃; for 6h; Take 7-methoxy benzofuran (XVII) (2g, 13.4mmol) soluble inwater dichloromethane (40ml) in, and then the reaction bottle the reaction bottle placed in dry ice acetone bath cooled to 78 C. then dropping borontribromide of dichloromethane solution(1M, 20 ml). The reaction mixture at -78 C maintain under 6 hours, Thenslowly rise to room temperature under the stirringovernight. use water (20 ml) after quenching, Reactionmixture [compound] use methyl tert-butyl ether extraction, the solvent isremoved under vacuum. Through column chromatography (25% EtOAc-hexane, toobtain light brown color Oily things 0.94g, yield 52%.
50% With pyridine hydrochloride; EXAMPLE 1C 7-Hydroxybenzofuran A mixture of 7methoxybenzofuran (1.8 g.) and pyridine hydrochloride (4.6 g.) was heated at 220 C. for 21/2 hours. The reaction was cooled and diluted with methylene chloride. The solution was washed with 5% aqueous hydrochloric acid (six times); dried (MgSO4) and concentrated to an oil, 0.8 g. (50% yield).
42% With boron tribromide; In dichloromethane; at -78 - 20℃;Inert atmosphere; To a stirred solution of <strong>[7168-85-6]7-methoxybenzofuran</strong> (3.3 mmol)) in dry DCM (5.0 mL) at -78 C. under N2 atmosphere was added BBr3 (3.0 mmol) (1.0M solution in DCM) and then the reaction was allowed to stir overnight at room temperature. The crude reaction was quenched with ice water and extracted with DCM (3×5.0 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The product was purified by column chromatography to give 51. [0380] benzofuran-7-ol (51) (42) 1H NMR (500 MHz, CDCl3) delta 7.60 (d, J=2.0 Hz, 1H), 7.16 (d, J=7 Hz, 1H), 7.10 (t, J=7.5 Hz, 1H), 6.83 (d, J=7.5 Hz, 1H), 6.77 (d, J=2.0 Hz, 1H), 5.43 (s, 1H). GC-MS (ES) for C8H6O2 [M]+ 134.
With hydrogenchloride; lithium iodide; In 2,3,5-trimethyl-pyridine; Reference Example 214 To a solution of <strong>[7168-85-6]7-methoxybenzofuran</strong> (8.0 g) in collidine (80 ml) was added lithium iodide (14.5 g), and the mixture was refluxed under argon atmosphere for 1 day and cooled. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate (twice). The organic layer was washed with 1N hydrochloric acid (twice), water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give dark brown oil of 7-hydroxybenzofuran (7.0 g). 1H-NMR (200 MHz, CDCl3) delta 5.45 (br, 1H), 6.78 (d, 1H, J=2.2 Hz), 6.84 (dd, 1H, J=7.0, 1.4 Hz), 7.09 (d, 1H, J=7.4 Hz), 7.17 (dd, IH, J=7.8, 1.8 Hz), 7.61 (d, 1H, J=2.2 Hz).
With boron trichloride; tetra-(n-butyl)ammonium iodide; In dichloromethane; at -78℃; for 6h; Preparation 13 Benzofuran-7-ol To 7-methoxy benzofuran (6.3 g, 42.5 mmol) in a 0.5 M solution of CH2Cl2 at -78 C. is added tetrabutylammonium iodide (18.9 g, 51 mmol). To this stirred solution, BCl3 (100 mL of a 1.0 M solution in CH2Cl2, 100 mmol) was added dropwise via addition funnel. The reaction mixture was stirred at -78 C. for 6 h. Water is added dropwise very slowly to quench. The resulting mixture was stirred overnight at rt, basified with 6 N NaOH (pH=10), stirred for 1 h, neutralized with 2 N HCl (pH=7), and extracted with CH2Cl2 (5*). The combined extracts were dried (MgSO4), filtered, concentrated, and chromatographed (10% EtOAc in hexanes) to provide 5.3 grams of benzofuran-7-ol as an oil. 1H NMR (400 MHz, CDCl3): delta 7.61 (d, 1, J=2.1), 7.19 (d, 1, J=7.7), 7.13 (t, 1, J=7.7), 6.88 (d, 1, J=7.7), 6.79 (d, 1, J=2.1), 6.04 (bs, 1). Previously prepared but no data reported: Musser, J. H.; Chakraborty, U.; Bailey, K.; Sciortino, S.; Whyzmuzis, C.; Amin, D.; Sutherland, C. A. J. Med. Chem. 1987, 30, 62-67.
prepared from <strong>[7168-85-6]7-methoxybenzo[b]furan</strong> according to a similar demethylation method as described in WO 04/043904)

  • 2
  • [ 4790-79-8 ]
  • [ 4790-81-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / Cu; quinoline / 2 h / Heating 2: 52 percent / BBr3 / CH2Cl2 / -78 - 20 °C
Multi-step reaction with 2 steps 1: 90 percent / Cu / quinoline / Heating 2: 50 percent / pyridine hydrochloride / 2.5 h / 200 °C
Multi-step reaction with 2 steps 1: aqueous hydrobromic acid; acetic acid 2: copper-powder; quinoline
Multi-step reaction with 2 steps 1: copper; quinoline / 2 h / 240 °C 2: boron tribromide / dichloromethane / 2 h / -78 °C
Multi-step reaction with 2 steps 1: copper / 2 h / Reflux 2: boron tribromide / water; dichloromethane / 6 h / -78 - 20 °C
Multi-step reaction with 2 steps 1: copper; quinoline / 2 h / Reflux 2: boron tribromide / dichloromethane / 4 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: quinoline; copper / 2 h / Reflux 2: boron tribromide / dichloromethane / 4 h / 0 - 20 °C

  • 3
  • [ 4790-81-2 ]
  • [ 42149-74-6 ]
  • 7-propoxyethoxybenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; potassium carbonate In water; N,N-dimethyl-formamide R.217 Reference Example 217 Reference Example 217 To a solution of 7-hydroxybenzofuran (2.609) in DMF (70 ml) were added potassium carbonate (6.97 g) and sodium iodide (7.55 g) and then was added 2-chloroethylpropylether (4.76 g), and the mixture was stirred, under nitrogen atmosphere, at 95° C. for 3 days and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give brown oil of 7-propoxyethoxybenzofuran (3.76 g). 1H-NMR (200 MHz, CDCl3) δ 0.93 (t, 3H, J=7.6 Hz), 1.55-1.73 (m, 2H), 3.53 (t, 2H, J=6.6 Hz), 3.88 (t, 2H, J=4.8 Hz), 4.37 (t, 2H, J=5.2 Hz), 6.76 (d, 1H, J=2.0 Hz), 6.84 (dd, 1H, J=7.4, 1.4 Hz), 7.13 (t, 1H, J=6.6 Hz), 7.21 (dd, 1H, J=7.6, 1.6 Hz), 7.62 (d, 1H, J=2.2 Hz).
  • 4
  • [ 4790-81-2 ]
  • [ 33301-41-6 ]
  • [ 1309209-02-6 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; Step 1: l-Benzhydryl-3-(benzofuran-7-yloxy)-azetidinePotassium carbonate (348 mg, 2.52 mmol) and benzofuran-7-ol (169 mg, 1.26 mmol) were successively added to a solution of l-benzhydrylazetidin-3-yl methanesulfonate (400 mg, 1.26 mmol) in DMF (8 mL). The reaction mixture was stirred overnight at 90C and then diluted by addition of ethyl acetate (20 mL) and water (20 mL). The aqueous phase was separated and extracted with ethyl acetate (4 x 50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (5 x 50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/dichloromethane (1 : 0 to 2 : 8 to 0 : 1) as eluent. The title product was obtained as a yellow oil (350 mg, 69%).LCMS (ESI-APCI) m/z 356.2 (M + H)+
  • 5
  • [ 174913-09-8 ]
  • [ 4790-81-2 ]
  • 7-(4-chloro-2-methoxyphenoxy)benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 90℃; for 24h;Inert atmosphere; Sealed tube; Synthesis of 7-(4-chloro-2-methoxyphenoxy)Benzofuran (52). Following step A2 in the synthetic scheme 1.2 from 51 to give 52 (20) 1H NMR (500 MHz, CDCl3) delta 7.62 (d, J=2.0 Hz, 1H), 7.32 (dd, J=8.0, 1.0 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 7.00 (d, J=2.0 Hz, 1H), 6.88-6.85 (m, 2H), 6.80 (d, J=2.0 Hz, 1H), 6.74 (d, J=8.0 Hz, 1H), 3.85 (s, 3H). GC-MS (ES) for C15H11ClO3 [M]+=274.
  • 6
  • [ 24410-55-7 ]
  • [ 4790-81-2 ]
  • 7
  • [ 4790-81-2 ]
  • [ 63485-50-7 ]
  • (trans)-methyl 3-(benzofuran-7-yloxy)cyclobutanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 72h; Triphenylphosphine (892 mg, 3.40 mmol) was added to a solution of benzofuran-7-ol (380 mg, 2.83 mmol) in tetrahydrofuran (7 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (0.36 mL, 3.4 mmol) was added, followed by DIAD (0.66 mL, 3.4 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc-hexanes gradient to give the title compound (373 mg, 45%). 1H NMR (400 MHz, CD3SOCD3) delta 2.34-2.46 (m, 2 H), 2.65-2.73 (m, 2 H), 3.15-3.25 (m, 1 H), 3.63 (s, 3 H), 4.90-5.01 (m, 1 H), 6.69 (d, J = 8 Hz, 1 H), 6.87-6.91 (m, 1 H), 7.10 (t, J = 8 Hz, 1 H), 7.20 (d, J = 8 Hz, 1 H), 7.90-7.93 (m, 1 H); LC-MS (LC-ES) M+H = 247.
  • 8
  • [ 4790-81-2 ]
  • [ 110677-54-8 ]
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