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[ CAS No. 1192-62-7 ] {[proInfo.proName]}

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Chemical Structure| 1192-62-7
Chemical Structure| 1192-62-7
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Product Details of [ 1192-62-7 ]

CAS No. :1192-62-7 MDL No. :MFCD00003242
Formula : C6H6O2 Boiling Point : -
Linear Structure Formula :C4H3O(COCH3) InChI Key :IEMMBWWQXVXBEU-UHFFFAOYSA-N
M.W : 110.11 Pubchem ID :14505
Synonyms :
2-Furyl methyl ketone
Chemical Name :1-(Furan-2-yl)ethanone

Safety of [ 1192-62-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P280-P302+P352+P312-P304+P340+P310-P305+P351+P338 UN#:2811
Hazard Statements:H300+H330-H311-H319 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1192-62-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1192-62-7 ]

[ 1192-62-7 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 1192-62-7 ]
  • [ 14150-94-8 ]
  • [ 131941-30-5 ]
  • 2
  • [ 1192-62-7 ]
  • [ 403-42-9 ]
  • [ 154258-82-9 ]
  • 3
  • [ 1192-62-7 ]
  • [ 616-38-6 ]
  • [ 615-06-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In toluene; mineral oil; for 5h;Reflux; General procedure: To a solution of ketone (20 mmol) in toluene (80 mL) was added dimethyl carbonate (60 mmol) and NaH (40 mmol, 60%). The reaction mixture was refluxed for 5 h until TLC indicated the total consumption of the ketone. After cooling, the reaction mixture was poured into ice-water (100 mL), acidified with 3 M HCl to pH 2-3 and extracted with EtOAc (100 mL x3). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether /EtOAc = 10/1) to afford the desired compound.
  • 4
  • [ 1192-62-7 ]
  • [ 3199-50-6 ]
YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide; In DMF (N,N-dimethyl-formamide); To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold water. The product was extracted with ether (200 mL, 3* times). Yield 61%, mp 92-93 C. (hexanes/ether, Lit. mp 94-95 C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931). 1H NMR (CDCl3); delta 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H). 13C NMR; delta 8185.4, 154.4, 128.2, 118.9,114.3, 25.7.
50.4% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 24h; To a solution of 1 (10 g, 90 mmol) in DMF 40 mL, NBS (19g, 108 mmol) was added by keeping the temperature at 0 C. Thereaction mixture was stirred overnight at room temperature. Upon completion,the reaction mixture was poured into ice-cold water. The mixture was dilutedwith EtOAc, and the insoluble material was filtered off through Celite. Theorganic layer of the filtrate was washed with brine, dried anhydrous magnesiumsulfate, and concentrated. The residue was chromatographed (SiO2,EtOAc/n-hexane, 1/19, v/v) to afford compound 2 (8.7 g, 45.4mmol, 50.4%). 1H NMR (500 MHz, CDCl3,delta, ppm): 2.46 (3H. s),6.49 (1H, d, J = 3.4 Hz), 7.12 (1H,d, J = 3.4 Hz). MS m/z 188 (M + H)+.
44.5% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 0.5h; Synthesis of 2-acetyl-5-bromofuran (29) 2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol). The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL x 2). The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29. Yield 1.68 g (yield rate 44.5%).
44.5% With N-Bromosuccinimide; In hexane; water; ethyl acetate; N,N-dimethyl-formamide; Synthesis of 2-acetyl-5-bromofuran (29) 2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol). The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL*2). The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29. Yield 1.68 g (yield rate 44.5%).
28% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of compound 4 (5.0 g, 45.45 mmol) and DMF (50 mL), NBS (8.8 g, 50 mmol) was added portion-wise at room temperature under stirring. The reaction mixture was allowed to stir at room temperature overnight. 50% starting material remained by TLC and LCMS. Reaction mixture was poured into cold water and the compound was extracted with diethyl ether (150 mL X 3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 5% ethyl acetate in n-hexane as an eluent to afford compound 43 (2.4 g, 28%) as a white solid.
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 5h; 2-Acetylfuran is dissolved in N,N-dimethylformamide (5 g, 1.1 mol/L), and N-bromosuccinimide (1 eq.) is added.After stirring for 5 hours at room temperature, the reaction mixture is poured into ice water and the precipitate formed is drained.1H NMR (300 MHz, CDCl3, delta in ppm): 2.47 (s, 3H); 6.49 (d, 1H, J=3.6 Hz); 7.12 (d, 1H, J=3.6 Hz).
With N-Bromosuccinimide; 90 mmol of 2-acetylfuran was dissolved in 40 mL of dimethylformamide (DMF), then 108 mmol of N-bromosuccinimide (NBS) was added at 0 C. The mixture was stirred overnight at room temperature. The mixture contained 1-(5 -bromo-2-furyl)ethanone after reaction. The reaction mixture described in Step 1 was diluted with ethyl acetate and filtered. The organic phase in the filtrate was washed with saturated salt solution and dried over anhydrous sodium sulfate, concentrated, and separated by chromatography to yield 1-(5-bromo-2-furyl)ethanone. 1H NMR (500 MHz, CDCl3, ?, ppm): 2.46 (3H. s), 6.49 (1H, d, J=3.4 Hz), 7.12 (1H, d, J=3.4 Hz). MS m/z 188 (M+H)+.

  • 6
  • [ 1192-62-7 ]
  • isopentyl magnesium halide [ No CAS ]
  • [ 615-06-5 ]
  • 7
  • [ 1192-62-7 ]
  • [ 50-00-0 ]
  • [ 25150-61-2 ]
  • [ 91247-20-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; isopropyl alcohol; at 90 - 95℃; for 0.5h;pH 4; General procedure: To a stirred mixture of 1-(furan-2-yl)ethanone (1a) or 1-(thiophen-2-yl)ethanone (1b) (10 mmol), <strong>[25150-61-2]pyrrolidine hydrochloride</strong> (10 mmol) and 1/5th of paraformaldehyde (10 mmol) in isopropanol (10 mL) was added conc. HCl dropwise to adjust the pH of the solution to 4. The reaction mixture was then heated in an oil bath at 90-95 C for 30 min with stirring. Other four portion of the paraformaldehyde were added at 15 min interval. The reaction mixture was further refluxed for 6-8 h. The solvent was distilled off. The residue obtained was washed with hexane (2 × 5 mL). The Mannich base of pyrrolidine obtained as a HCl salt were used further without purification.A mixture of above Mannich salt (10 mmol) and imidazole/1H-1,2,4-triazole (12 mmol) in 10 mL ethanol : water (3:2) was heated for 5-9 h at 90 C. The organic solvent was distilled off and the compound was extracted with dichloromethane (2 × 5 mL). The combined organic layer was dried over sodium sulphate and concentrated to give the crude product which was purified by column chromatography using methanol: chloroform (1: 99) as an eluant to provide the required compounds (2a-2d).
  • 8
  • chitosan, Mw = 760000, degree of deacetylation DD = 85.5%, [ No CAS ]
  • [ 109-08-0 ]
  • [ 1122-62-9 ]
  • [ 1192-62-7 ]
  • [ 2214-53-1 ]
  • [ 85279-30-7 ]
  • [ 1072-83-9 ]
  • [ 1262900-24-2 ]
  • [ 99969-04-7 ]
  • [ 32736-95-1 ]
  • [ 74376-36-6 ]
  • 9
  • [ 1455-20-5 ]
  • [ 1192-62-7 ]
  • [ 1401352-35-9 ]
  • 10
  • [ 1192-62-7 ]
  • [ 17823-69-7 ]
  • [ 261761-63-1 ]
  • 11
  • [ 1192-62-7 ]
  • [ 541539-88-2 ]
  • 1-(5-(5-methoxy-2-methyl-2H-indazol-3-yl)furan-2-yl)ethan-1-one [ No CAS ]
  • 12
  • [ 1192-62-7 ]
  • [ 383-62-0 ]
  • [ 2250-39-7 ]
YieldReaction ConditionsOperation in experiment
With lithium hexamethyldisilazane; In tetrahydrofuran; at 0℃; for 1h;Inert atmosphere; Compounds 1 and 2 were dissolved in THF. Subsequently, LiHMDS was added dropwise. The reaction was carried out under Argon atmosphere at 0C for about 1 h after LiHMDS had been added. The solvent was evaporated and the reaction mixture was purified by adding a 1 :1 mixture of EtOAc/6M aq.HCI, separating the aqueous phase, and subsequent washes of the organic phase 1 :1 with H2O and brine. Final traces of H2O were removed with Na2SO4 and finally the organic solvent was removed by evaporation.
  • 13
  • [ 3375-31-3 ]
  • [ 81-07-2 ]
  • [ 607-01-2 ]
  • [ 1192-62-7 ]
YieldReaction ConditionsOperation in experiment
66% General procedure: Complexes 4, 6, 8 and 10-12 were prepared by the following method. SacH (0.5mmol, 91.6mg) in water (5mL) was added to a solution of Pd(OAc)2 (0.25mmol, 56.1mg) in MeCN (10mL) and the solution was stirred for 30min at rt. Then, the corresponding phosphine (0.5mmol) in MeOH (10mL) was added to this solution and the resulting solutions were refluxed over a day. Complexes 2, 5 and 9 were synthesized using the same procedure, but the SacH/phosphine ratio was 2:1. In the case of 9, DMSO (10mL) was added to the reaction medium to dissolve the solid particles. The powders of these complexes were obtained after removal of the solvents using a rotary evaporator.
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