[ CAS No. 1914-60-9 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1914-60-9
Chemical Structure| 1914-60-9
Structure of 1914-60-9

Quality Control of [ 1914-60-9 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 1914-60-9 ]

SDS

Product Details of [ 1914-60-9 ]

CAS No. :1914-60-9MDL No. :MFCD03086168
Formula :C9H8O3Boiling Point :340.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :WEVFUSSJCGAVOH-UHFFFAOYSA-N
M.W :164.16Pubchem ID :2776555
Synonyms :

Computed Properties of [ 1914-60-9 ]

TPSA : 46.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.22 Rotatable Bond Count : 1

Safety of [ 1914-60-9 ]

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 of [ 1914-60-9 ]

  • Upstream synthesis route of [ 1914-60-9 ]
  • Downstream synthetic route of [ 1914-60-9 ]

[ 1914-60-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 496-41-3 ]
  • [ 1914-60-9 ]
YieldReaction ConditionsOperation in experiment
74% With hydrogen In ethyl acetate for 48.00 h; a)
(R,S)-2,3-Dihydro-benzofuran-2-carboxylic acid (54a)
Commercially available benzofuran-2-carboxylic acid (Aldrich Chemical Company) (27 g, 167.7 mmol) was dissolved in ethyl acetate (300 mL) and hydrogenated in the presence of 10percent Pd/C (20 g) at 65-70 psi for 2 days.
After filtration of the solution and evaporation of the solvent, a mixture of solvent (ethyl acetate-hexane, 1:6) was added to the residue.
The title compound was obtained as a crystalline solid by filtration (20.23 g, 74percent).
m.p: 116-117° C.; 1H NMR (300 MHz, CDCl3) δ: 11.05 (brs, 1H), 7.17 (m, 2H), 6.91 (m, 2H), 5.24 (dd, 1H), 3.63 (dd, 1H), 3.42 (dd, 1H).
Reference: [1] Patent: US2005/54630, 2005, A1. Location in patent: Page/Page column 42
[2] Justus Liebigs Annalen der Chemie, 1883, vol. 216, p. 169
[3] Chemische Berichte, 1906, vol. 39, p. 496
[4] Farmaco, 1998, vol. 53, # 12, p. 764 - 772
[5] Patent: US2008/200540, 2008, A1. Location in patent: Page/Page column 18
  • 2
  • [ 66158-96-1 ]
  • [ 1914-60-9 ]
YieldReaction ConditionsOperation in experiment
77% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In tetrahydrofuran; water for 3.00 h; To a stirred solution of 6 (119 mg, 0.792 mmol) in tetrahydrofuran (THF) and saturated NaHCO3 solution (1:1) (12 mL) was added TEMPO (2,2,6,6,-tetramethylpiperidine-1-oxyl) (24.0 mg, 0.154 mmol), ΚBr (24.0 mg, 0.202 mmol), and NaOCl aq (2.38 mL). After stirring for 3h, the reaction mixture was diluted by diethyl ether (20 mL) and acidified with 1N HCl to pH 2. The mixture was extracted with EtOAc (3 × 20 mL) and the combined extracts were dried over anhydrous Na2SO4. After evaporation, the product was dried in vacuo to afford the desired 2,3-dihydrobenzofuran-2-carboxylic acid (7) (100 mg, 77percent) as a yellow solid. m.p. 116 – 118 ; 1HNMR (CDCl3, 300 MHz) δ 7.15 (m, 2H), 6.89 (d, 1H, J = 7.7 Hz),6.88 (t, 1H, J = 7.7 Hz), 5.19 (dd,1H, J = 10.5, 7.0 Hz), 3.55 (dd, 1H, J = 15.8, 10.5 Hz), 3.37 (dd, 1H, J = 15.8, 7.0 Hz); FTIR (neat) 3391, 3049, 1047cm-1
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2545 - 2549
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260
  • 3
  • [ 1745-81-9 ]
  • [ 1914-60-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2545 - 2549
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260
  • 4
  • [ 41873-61-4 ]
  • [ 1914-60-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 495 - 496
  • 5
  • [ 111080-48-9 ]
  • [ 1914-60-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 495 - 496
  • 6
  • [ 111080-49-0 ]
  • [ 1914-60-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 495 - 496
  • 7
  • [ 1746-13-0 ]
  • [ 1914-60-9 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260
  • 8
  • [ 108-95-2 ]
  • [ 1914-60-9 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260
  • 9
  • [ 43119-53-5 ]
  • [ 1914-60-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 495 - 496
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