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[ CAS No. 849517-65-3 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 849517-65-3
Chemical Structure| 849517-65-3
Structure of 849517-65-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 849517-65-3 ]

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Product Details of [ 849517-65-3 ]

CAS No. :849517-65-3MDL No. :MFCD13152331
Formula : C7H5IO2 Boiling Point : 261.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :248.02Pubchem ID :18788521
Synonyms :

Computed Properties of [ 849517-65-3 ]

TPSA : 18.5 H-Bond Acceptor Count : 2
XLogP3 : 2.4 H-Bond Donor Count : 0
SP3 : 0.14 Rotatable Bond Count : 0

Safety of [ 849517-65-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 849517-65-3 ]

  • Upstream synthesis route of [ 849517-65-3 ]
  • Downstream synthetic route of [ 849517-65-3 ]

[ 849517-65-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 75-11-6 ]
  • [ 25245-33-4 ]
  • [ 849517-65-3 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere
Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 1.00 h; Inert atmosphere
To a solution of 34a (792 mg, 3.00 mmol) in CH2Cl2 (10.0 mL) was added BBr3 (1.0 M CH2Cl2 solution, 14.0 mL, 14.0 mmol) at -78 °C under Ar atmosphere, and the mixture was stirred at the room temperature. After 42 h, the reaction mixture was poured into ice, and volatile materials were removed under reduced pressure. The residue was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was dissolved in DMF (30 mL), and to this were added Cs2CO3 (1.00 g, 3.07 mmol) and CH2I2 (250 mL, 3.10 mmol) and the mixture was stirred at 120 °C for 1 h under Ar atmosphere. After the reaction mixture was cooled to room temperature, DMF was removed under reduced pressure. To the residue were added ethyl acetate and water, and the resulting insoluble material was removed by filtration and washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate = 50:1) to give 34b [563 mg, 2.27 mmol, 76percent (2 steps)] as a white solid. Mp 35.5-37.0 °C; 1H NMR (CDCl3, 500 MHz) δ 7.11 (dd, J = 1.2, 8.6 Hz, 1H), 6.75 (dd, J = 1.2, 7.9 Hz, 1H), 6.78 (dd, J = 7.9, 8.6 Hz, 1H), 5.99 (s, 2H); MS (FAB) m/z 248 (M)+.
76%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 18.00 h;
Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 1.00 h;
Anhydrous dichloromethane (10 ml) and boron tribromide (1.0 M dichloromethane solution, 14.0 ml, 14.0 mmol) were added to 3-iodo-1,2-dimethoxybenzene (i) (792 mg, 3.00 mmol) at -78° C., and the mixture was agitated at room temperature for 18 hours. The reaction solution was poured into iced water, dichloromethane was evaporated under a reduced pressure, and an organic phase was extracted with ethyl acetate. The organic phase was washed with an aqueous solution of saturated sodium chloride, and the resultant was dried over sodium sulfate, followed by concentration under a reduced pressure. Anhydrous N,N-dimethylformamide (30 ml), cesium carbonate (1.00 g, 3.07 mmol), and diiodomethane (0.250 ml, 3.10 mmol) were added to the residue, and the mixture was agitated at 120° C. for 1 hour. N,N-dimethylformamide was evaporated under a reduced pressure, water was added thereto, and an organic phase was extracted with ethyl acetate. The organic phase was washed with water and an aqueous solution of saturated sodium chloride, and the resultant was dried over sodium sulfate, followed by concentration under a reduced pressure. A crude product was purified via silica gel column chromatography using hexane:ethyl acetate (50:1) as an eluting solvent (yield: 563 mg, 76percent).
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2675 - 2687
[2] Patent: US2012/316342, 2012, A1. Location in patent: Page/Page column 24
  • 2
  • [ 91-16-7 ]
  • [ 849517-65-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2675 - 2687
[2] Patent: US2012/316342, 2012, A1
  • 3
  • [ 111726-43-3 ]
  • [ 849517-65-3 ]
Reference: [1] Helvetica Chimica Acta, 2012, vol. 95, # 11, p. 2194 - 2217
  • 4
  • [ 533-31-3 ]
  • [ 849517-65-3 ]
Reference: [1] Helvetica Chimica Acta, 2012, vol. 95, # 11, p. 2194 - 2217
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