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[ CAS No. 13196-11-7 ]

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2D
Chemical Structure| 13196-11-7
Chemical Structure| 13196-11-7
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Product Details of [ 13196-11-7 ]

CAS No. :13196-11-7MDL No. :MFCD08669481
Formula : C8H6O2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :134.13Pubchem ID :128844
Synonyms :

Computed Properties of [ 13196-11-7 ]

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

Safety of [ 13196-11-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13196-11-7 ]

  • Upstream synthesis route of [ 13196-11-7 ]
  • Downstream synthetic route of [ 13196-11-7 ]

[ 13196-11-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 13196-11-7 ]
  • [ 74-88-4 ]
  • [ 50551-63-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 10, p. 997 - 1001
  • 2
  • [ 13196-11-7 ]
  • [ 6272-26-0 ]
  • [ 1020947-92-5 ]
  • [ 23681-89-2 ]
YieldReaction ConditionsOperation in experiment
92% With ammonium chloride In tetrahydrofuran; hydrogenchloride; methanol; ethyl acetate Preparation 3
2,3-Dihydro-benzofuran-6-ol
6-Hydroxy-2H-benzofuran-3-one (3 g) was suspended in anhydrous tetrahydrofuran under an argon atmosphere and cooled to 0° C. Lithium aluminium hydride (20 ml of a 1M solution in tetrahydrofuran) was added dropwise over 10 min and the reaction allowed to reach room temperature over 2 hours.
The reaction was cooled to 0° C. and treated dropwise with saturated ammonium chloride solution.
Ethyl acetate (200 ml) was added and the mixture filtered through Celite. The ethyl acetate layer was separated, dried (MgSO4) and evaporated to dryness under reduced pressure.
The resulting mixture of 2,3-dihydro-benzofuran-3,6-diol and benzofuran-6-ol (approximately 1:1 by 250 MHz 1H NMR) was dissolved in a mixture of hydrochloric acid (200 ml, 5M aqueous solution) and methanol (300 ml) and palladium hydroxide (0.5 g) added.
The mixture was stirred under a hydrogen atmosphere for 3 hours then filtered through Celite.
The organics were removed by evaporation under reduced pressure and the resulting solution neutralised with concentrated anmmonia solution.
The product was extracted into dichloromethane.
The dichloromethane solution was dried (MgSO4) and evaporated to dryness under reduced pressure to yield the title compound (2.5 g, 92percent).
1H NMR (250 MHz, CDCl3) δ: 3.11 (2H, t, J=8.4 Hz), 4.57 (2H, t, J=8.4 Hz), 6.27-6.34 (2H, m), 6.92-7.02 (1H, m); m/z (API+): 139.1 (M+3H+).
Reference: [1] Patent: US6465493, 2002, B1,
  • 3
  • [ 1020947-92-5 ]
  • [ 13196-11-7 ]
  • [ 23681-89-2 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 9, p. 1307 - 1313
[2] Synthetic Communications, 2014, vol. 44, # 9, p. 1307 - 1313
  • 4
  • [ 13196-11-7 ]
  • [ 23681-89-2 ]
Reference: [1] Chemische Berichte, 1936, vol. 69, p. 1087,1089
[2] Bulletin of the Chemical Society of Japan, 1938, vol. 13, p. 653
  • 5
  • [ 6272-26-0 ]
  • [ 13196-11-7 ]
  • [ 23681-89-2 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 9, p. 1307 - 1313
  • 6
  • [ 13196-11-7 ]
  • [ 588703-29-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1,
[3] Patent: WO2008/141119, 2008, A2,
  • 7
  • [ 13196-11-7 ]
  • [ 1083168-69-7 ]
Reference: [1] Patent: WO2008/141119, 2008, A2,
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