[ CAS No. 166599-84-4 ]

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2D
Chemical Structure| 166599-84-4
Chemical Structure| 166599-84-4
Structure of 166599-84-4

Quality Control of [ 166599-84-4 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 166599-84-4 ]

SDS

Product Details of [ 166599-84-4 ]

CAS No. :166599-84-4MDL No. :MFCD10000600
Formula :C9H6O3Boiling Point :325.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :162.14Pubchem ID :22324117
Synonyms :

Computed Properties of [ 166599-84-4 ]

TPSA : 50.4 H-Bond Acceptor Count : 3
XLogP3 : 1.9 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 166599-84-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 166599-84-4 ]

  • Upstream synthesis route of [ 166599-84-4 ]
  • Downstream synthetic route of [ 166599-84-4 ]

[ 166599-84-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 41019-56-1 ]
  • [ 166599-84-4 ]
YieldReaction ConditionsOperation in experiment
99% With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 16.00 h; A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a solution of 131 (2.02 g, 11.4 mmol) in THF (20mL) and MeOH (20 mL) and the solution was stirred at r.t. for 16 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HC1 and the precipitate was filtered and dried to give 132 (1.83 g, 99percent). 1H NMR (DMSO-d6) δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Found: [M-H] = 161.1.
99%
Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 16.00 h;
Stage #2: With hydrogenchloride In water
A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) wasadded to a solution of the above ester (2.02 g, 11.4 mmol) in THF(20 mL) and MeOH (20 mL) and the solution was stirred at 20 Cfor 16 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl and the precipitate was filteredand dried to give benzofuran-4-carboxylic acid (1.83 g,99percent). 1H NMR (DMSO d6) d 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H),7.85–7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz,1H). Found: [MH] = 161.1.
Reference: [1] Patent: WO2017/155909, 2017, A1. Location in patent: Paragraph 0190
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 2
  • [ 166599-85-5 ]
  • [ 166599-84-4 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: for 5.47 h; Heating / reflux
Stage #2: With sodium hydroxide; water In toluene at 60℃; for 9.00 h;
Stage #3: With hydrogenchloride In water at 2 - 14℃; for 14.50 h; Heating / reflux
A solution of Intermediate 10 in toluene (1 wt in 6.6 vol) was added to a refluxing mixture of p-toluenesulfonic acid (0.03 eq., 0.03 wt) in toluene (3.8 vol) over 43 minutes. The mixture was stirred under reflux for 33 minutes then solvent (1.1 vol) was withdrawn at 130 0C jacket temperature under slightly reduced pressure (1000- 880 mbar). The mixture was further stirred at reflux. 4.25 hours after the addition of Intermediate 10 the mixture was cooled to 25 0C. The mixture was filtered over silica gel (1.1 wt) that had been conditioned with toluene (4.1 vol). The silica plug was further washed with toluene (8.2 vol). The product containing fractions were combined (total volume 10.8 vol). Solvent (8.6 vol) was withdrawn at 80 0C jacket temperature under reduced pressure. Toluene (0.6 vol) and 1.0 M NaOH (1.5 eq., 7.7 vol) was added and the two-phase mixture was stirred at 60 0C for 9 hours. After cooling to 20 0C the phases were separated and 32percent HCI (1.7 vol) was added at 2- 14°C to the aqueous phase. After addition of 9.4 vol toluene the mixture was stirred under reflux for 14.5 hours. The suspension was cooled to 20 0C and THF (5.3 vol) was added. The phases were separated and the organic layer was washed two times with a mixture of 5.6 vol water and 0.6 vol THF. 10.3 vol of solvent was distilled off at 80 0C jacket temperature and reduced pressure before 3.2 vol toluene was added. The mixture was refluxed for 33 minutes (ambient pressure), cooled to 0 0C over 3 hours and stirred at that temperature for 2.5 days. The precipitate was filtered, dried for 2 hours in a stream of nitrogen and dried in a rotavap at 50 0C to give the title compound as an off-white solid. Yield (percent theory): 62percent
Reference: [1] Patent: WO2009/34133, 2009, A1. Location in patent: Page/Page column 18
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 3
  • [ 79250-46-7 ]
  • [ 166599-84-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 4
  • [ 79950-39-3 ]
  • [ 166599-84-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 5
  • [ 177734-79-1 ]
  • [ 166599-84-4 ]
Reference: [1] Patent: WO2017/155909, 2017, A1
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 6
  • [ 480-97-7 ]
  • [ 166599-84-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
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