[ CAS No. 25177-85-9 ]

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CAS No. 25177-85-9, is an aryls compound, with a molecular weight of 162.19, molecular formula C10H10O2, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Product Details

CAS No. :25177-85-9MDL No. :MFCD00085095
Formula :C10H10O2InChI Key :XUDCMQBOWOLYCF-UHFFFAOYSA-N
M.W :162.19Pubchem ID :575777
Boiling Point :-
Synonyms :

Computed Properties

TPSA : 37.3 H-Bond Acceptor Count : 2
XLogP3 : 1.7 H-Bond Donor Count : 1
SP3 : 0.30 Rotatable Bond Count : 1

Safety

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

Application In Synthesis

[ 25177-85-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 26453-01-0 ]
  • [ 25177-85-9 ]
YieldReaction ConditionsOperation in experiment
87% With hydrogenchloride In 1,4-dioxane; water at 60 - 70℃; for 41.00 h; 2-lndanecarboxylic Acid (129). A mixture of 2-indanecarbonitrile (128) (Ksander, G.M. et al., J. Med. Chem. 2001, 44, 4677) (55.1 g, 0.385 mol), cHCI (100 mL) and dioxane (500 mL) was stirred at 60-70 0C for 41 h. The mixture was cooled and dioxane evaporated to give a residue, which was suspended in 1 M HCI (300 mL) and stirred at 20 0C for 15 h. The solid was filtered, washed with water and dried to give acid 129 (54.1 g, 87percent) as a white solid: mp (EtOAc/pet. ether) 128 0C [lit. (Baeyer, A. Perkin W.H., Chem. Ber. 1884, 17, 122) mp 130.2 0C]; 1H NMR δ 10.50 (br s, 1 H, CO&2H), 7.14-7.25 (m, 4 H, H-4, H-5, H-6, H-7), 3.21-3.43 (m, 5 H, H-1 , H-2, H-3)
Reference: [1] Patent: WO2006/104406, 2006, A1. Location in patent: Page/Page column 112
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865
  • 2
  • [ 66014-45-7 ]
  • [ 25177-85-9 ]
YieldReaction ConditionsOperation in experiment
71% With lithium hydroxide In ethanol Dissolve 2,2-dicarbethoxy-indane (5.67 g, 21.7 mmol) in ethanol (150 mL).
Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature.
Reflux for 1 hour and concentrate the solution in vacuo.
Partition between ethyl acetate and 6N hydrochloric acid.
Separate the organic phase and wash with brine.
Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid.
Distill (120°-160° C.at;0.2-0.5 mmHg) to give 2-carboxy-indane (2.5 g, 71percent).
71% With lithium hydroxide In ethanol Dissolve 2,2-dicarboethoxy-indan (5.67 g, 21.7 mmol) in ethanol (150 mL).
Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature.
Reflux for 1 hour and concentrate the solution in vacuo.
Partition between ethyl acetate and 6N hydrochloric acid.
Separate the organic phase and wash with brine.
Dry (MgSO4) and evaporate the solvent i n vacuo to give an off-white solid.
Distill (120°-160° C. at;0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71percent).
71% With lithium hydroxide In ethanol Dissolve 2,2-dicarboethoxy-indan (5.67 g, 21.7 mmol) in ethanol (150 mL).
Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature.
Reflux for 1 hour and concentrate the solution in vacuo.
Partition between ethyl acetate and 6N hydrochloric acid.
Separate the organic phase and wash with brine.
Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid.
Distill (120°-160° C. at;0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71percent).
71% With lithium hydroxide In ethanol Dissolve 2,2-dicarboethoxy-indane (5.67 g, 21.7 mmol) in ethanol (150 mL).
Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature.
Reflux for 1 hour and concentrate the solution in vacuo.
Partition between ethyl acetate and 6N hydrochloric acid.
Separate the organic phase and wash with brine.
Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid.
Distill (120°-160° C. at;0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71percent).

Reference: [1] Patent: US5252601, 1993, A
[2] Patent: US5420271, 1995, A
[3] Patent: US5428158, 1995, A
[4] Patent: US5604221, 1997, A
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996
  • 3
  • [ 81290-34-8 ]
  • [ 25177-85-9 ]
YieldReaction ConditionsOperation in experiment
69% With potassium hydroxide In ethanol; dichloromethane; water Dissolve 2-(carboethoxy)indan (6.49 g, 34.1 mmol) in ethanol (95percent, 150 mL) and water (75 mL).
Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour.
Partition between water (150 mL) and ethyl ether (2*150 mL).
Acidify the aqueous phase with hydrochloric acid to pH 1.
Extract with methylene chloride (2*150 mL), dry (Na2 SO4) and evaporate the solvent in vacuo to give 2-indancarboxylic acid as a tan solid (3.82 g, 69percent).
69% With potassium hydroxide In ethanol; dichloromethane; water Dissolve 2-(carboethoxy)indan (6.49 g, 34.1mmol) in ethanol (95percent, 150 mL) and water (75 mL).
Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour.
Partition between water (150 mL) and ethyl ether (2*150 mL).
Acidify the aqueous phase with hydrochloric acid to pH 1.
Extract with methylene chloride (2*150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 2-indancarboxylic acid as a tan solid (3.82 g, 69percent).
69% With potassium hydroxide In ethanol; dichloromethane; water Dissolve 2-(carboethoxy)indane (6.49 g, 34.1 mmol) in ethanol (95percent, 150 mL) and water (75 mL).
Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for hour.
Partition between water (150 mL) and ethyl ether (2*150 mL).
Acidify the aqueous phase with hydrochloric acid to pH 1.
Extract with methylene chloride (2*150 mL), dry (Na2 SO4) and evaporate the solvent in vacuo to give 2-indancarboxylic acid as a tan solid (3.82 g, 69percent).
Reference: [1] Patent: US5420271, 1995, A
[2] Patent: US5428158, 1995, A
[3] Patent: US5604221, 1997, A
[4] Journal of the South African Chemical Institute, 1957, vol. 10, p. 5,10
  • 4
  • [ 2437-08-3 ]
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Reference: [1] Journal of the Chemical Society, 1888, vol. 53, p. 7
[2] Chemische Berichte, 1884, vol. 17, p. 124
[3] Chemische Berichte, 1893, vol. 26, p. 2251[4] Journal of the Chemical Society, 1894, vol. 65, p. 233
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996
[6] Patent: US5840729, 1998, A
[7] Patent: US6262087, 2001, B1
[8] Patent: US6352988, 2002, B2. Location in patent: Page column 22
[9] Journal of Materials Chemistry A, 2014, vol. 2, # 44, p. 18823 - 18830
[10] Patent: US5047534, 1991, A
  • 5
  • [ 141738-19-4 ]
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Reference: [1] Patent: EP885869, 1998, A1
  • 6
  • [ 124-38-9 ]
  • [ 95-13-6 ]
  • [ 25177-85-9 ]
  • [ 2437-09-4 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 13969 - 13972
  • 7
  • [ 91-13-4 ]
  • [ 25177-85-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996
[2] Journal of Materials Chemistry A, 2014, vol. 2, # 44, p. 18823 - 18830
[3] Patent: US5047534, 1991, A
  • 8
  • [ 88-99-3 ]
  • [ 105-53-3 ]
  • [ 25177-85-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4216 - 4220
  • 9
  • [ 13070-90-1 ]
  • [ 25177-85-9 ]
Reference: [1] Journal of the South African Chemical Institute, 1957, vol. 10, p. 5,10
  • 10
  • [ 55589-21-4 ]
  • [ 25177-85-9 ]
Reference: [1] Journal of the South African Chemical Institute, 1957, vol. 10, p. 5,10
  • 11
  • [ 106167-47-9 ]
  • [ 25177-85-9 ]
Reference: [1] Journal of the South African Chemical Institute, 1957, vol. 10, p. 5,10
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