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[ CAS No. 4790-81-2 ]

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2D
Chemical Structure| 4790-81-2
Chemical Structure| 4790-81-2
Structure of 4790-81-2 *Storage: {[proInfo.prStorage]}

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Product Details of [ 4790-81-2 ]

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

Computed Properties of [ 4790-81-2 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 4790-81-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing 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   1~1

  • 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)

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