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[ CAS No. 52914-23-5 ]

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Chemical Structure| 52914-23-5
Chemical Structure| 52914-23-5
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Product Details of [ 52914-23-5 ]

CAS No. :52914-23-5 MDL No. :MFCD00173705
Formula : C8H9IO Boiling Point : 275.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :248.06 g/mol Pubchem ID :3040770
Synonyms :

Safety of [ 52914-23-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52914-23-5 ]

  • Upstream synthesis route of [ 52914-23-5 ]
  • Downstream synthetic route of [ 52914-23-5 ]

[ 52914-23-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 1798-06-7 ]
  • [ 52914-23-5 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With borane-THF In tetrahydrofuran at 20℃; for 6 h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
To a stirred solution of 2-(4-iodophenyl)acetic acid (2.00 g, 7.63 mmol) in tetrahydrofuran (150 ml_) at room temperature was added borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 7.63 ml_, 7.63 mmol). The resulting solution was stirred for 6 hours prior to dilution with brine, adjustment to pH = 13 with NaOH, and extraction with ethyl εicetate. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford 192a (620 mg, 33percent) as a light orange solid which was used in the subsequent reaction without further purification. LRMS (ESI): (calc) 248.1 ; (found) 271.1 (M+Na)+
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 34, p. 7865 - 7869
[2] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 1828 - 1833
[3] Liebigs Annalen der Chemie, 1994, # 11, p. 1075 - 1092
[4] Patent: WO2006/102760, 2006, A1, . Location in patent: Page/Page column 121
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 5, p. 647 - 652
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 11, p. 2319 - 2324
[7] Angewandte Chemie - International Edition, 2015, vol. 54, # 43, p. 12777 - 12781[8] Angew. Chem., 2015, vol. 127, # 43, p. 12968 - 12972,5
  • 2
  • [ 104-10-9 ]
  • [ 52914-23-5 ]
YieldReaction ConditionsOperation in experiment
82.5% With potassium iodide; sulfuric acid; nitrogen; sodium nitrite In hexane; water; ethyl acetate C.
2-(4-Iodophenyl)ethanol)
To a 500 mL 3-neck round-bottomed flask equipped with dropping funnel and nitrogen inlet were added 20.5 g (150 mmol) 2-(4-aminophenyl)ethanol and 100 mL hot water to give a solution A solution of 3.5 mL concentrated sulfuric acid in 10 mL water was added dropwise, and the solution cooled to 4° C.
A solution of 13.5 mL concentrated sulfuric acid in 50 mL water was added dropwise while maintaining the temperature between 0° C. and 5° C., then a solution of 13 g (188 mmol) sodium nitrite in 50 mL water was added dropwise at the same temperature.
After stirring 30 min at 0-5° C., a solution of 85 g (512 mmol) potassium iodide in 100 mL water was added dropwise, and the reaction was allowed to warm to room temperature and stirred for 2 hour.
The reaction was then heated to 60° C. for 30 min, cooled to room temperature, and extracted into ethyl acetate (2*250 mL).
The ethyl acetate layer was washed with aqueous sodium thiosulfate solution and brine, dried over sodium sulfate, and evaporated.
The residue was chromatographed on silica gel using 20percent and 50percent ethyl acetate in hexane as eluant to afford 30.7 g (82.5percent) of the product as a light yellow solid.
1H-NMR (CDCl, δ): 2.74 (m, 2H), 3.79 (m, 2H), 6.93 (m, 2H), 7.57 (m, 2H).
13C-NMR (CDCl3, δ): 38.6, 63.3, 91.7, 131.1, 137.6, 138.3. MS(percent): 247 (parent, 23).
Reference: [1] Journal of the Chemical Society, 1941, p. 652,657
[2] Journal of the Chemical Society, 1935, p. 1819
[3] Patent: US6235747, 2001, B1,
  • 3
  • [ 4654-39-1 ]
  • [ 52914-23-5 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 7, p. 2711 - 2714
[2] Patent: WO2005/63239, 2005, A1, . Location in patent: Page/Page column 134
  • 4
  • [ 60-12-8 ]
  • [ 18282-51-4 ]
  • [ 52914-23-5 ]
  • [ 100-52-7 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 1004 - 1005
  • 5
  • [ 103-45-7 ]
  • [ 52914-23-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1976, vol. 19, p. 1362 - 1366
[2] Patent: US4022814, 1977, A,
[3] Patent: US4175544, 1979, A,
  • 6
  • [ 101251-45-0 ]
  • [ 52914-23-5 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 657,659[2] Chem.Abstr., 1957, p. 280
  • 7
  • [ 60-12-8 ]
  • [ 52914-23-5 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 657,659[2] Chem.Abstr., 1957, p. 280
  • 8
  • [ 100-27-6 ]
  • [ 52914-23-5 ]
Reference: [1] Journal of the Chemical Society, 1941, p. 652,657
  • 9
  • [ 52914-23-5 ]
  • [ 162358-07-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4605 - 4616
  • 10
  • [ 52914-23-5 ]
  • [ 162358-05-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4605 - 4616
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