[ CAS No. 908247-29-0 ]

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Product Details

CAS No. :908247-29-0MDL No. :MFCD17171061
Formula :C12H10O2InChI Key :QVHNCHIMHYMBHR-UHFFFAOYSA-N
M.W :186.21Pubchem ID :44541372
Boiling Point :-
Synonyms :

Computed Properties

TPSA : 37.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.25 Rotatable Bond Count : 2

Safety

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

[ 908247-29-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 908247-29-0 ]
  • [ 31938-11-1 ]
  • [ 1193365-09-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6790 - 6802

[ 908247-29-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1190044-80-4 ]
  • [ 908247-29-0 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 15 - 30℃; for 3.50 h; Reflux
Stage #2: With hydrogenchloride In water at 15 - 30℃; for 0.50 h;
Reference Example 88; 4-(cyclopropylethynyl)benzoic acid; [Show Image] Ethyl 4-(cyclopropylethynyl)benzoate (2.894 g) obtained in Reference Example 87 was dissolved in a mixed solvent of methanol (10 mL), water (10 mL) and THF (15 mL), lithium hydroxide monohydrate (0.70 g) was added thereto, and the mixture was stirred at room temperature for 30 min, and heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was suspended in water, and the suspension was acidified with 1N aqueous hydrochloric acid solution (20 mL), and stirred at room temperature for 30 min. The obtained suspension was filtered, and the solid was collected by filtration was washed with water, and dried to give the title compound (2.458 g, yield 79percent) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ: 0.71 - 0.82 (2 H, m) 0.86 - 0.99 (2 H, m) 1.46 - 1.66 (1 H, m) 7.46 (2 H, d, J=8.71 Hz) 7.87 (2 H, d, J=8.33 Hz) 13.08 (1 H, br. s.).
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6790 - 6802
[2] Patent: EP2261213, 2010, A1. Location in patent: Page/Page column 76
  • 2
  • [ 1190044-80-4 ]
  • [ 908247-29-0 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 15 - 30℃; for 3.50 h; Reflux
Stage #2: With hydrogenchloride In water at 15 - 30℃; for 0.50 h;
Reference Example 88; 4-(cyclopropylethynyl)benzoic acid; [Show Image] Ethyl 4-(cyclopropylethynyl)benzoate (2.894 g) obtained in Reference Example 87 was dissolved in a mixed solvent of methanol (10 mL), water (10 mL) and THF (15 mL), lithium hydroxide monohydrate (0.70 g) was added thereto, and the mixture was stirred at room temperature for 30 min, and heated under reflux for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was suspended in water, and the suspension was acidified with 1N aqueous hydrochloric acid solution (20 mL), and stirred at room temperature for 30 min. The obtained suspension was filtered, and the solid was collected by filtration was washed with water, and dried to give the title compound (2.458 g, yield 79percent) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ: 0.71 - 0.82 (2 H, m) 0.86 - 0.99 (2 H, m) 1.46 - 1.66 (1 H, m) 7.46 (2 H, d, J=8.71 Hz) 7.87 (2 H, d, J=8.33 Hz) 13.08 (1 H, br. s.).
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6790 - 6802
[2] Patent: EP2261213, 2010, A1. Location in patent: Page/Page column 76
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