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[ CAS No. 85-42-7 ]

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2D
Chemical Structure| 85-42-7
Chemical Structure| 85-42-7
Structure of 85-42-7 *Storage: {[proInfo.prStorage]}

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Product Details of [ 85-42-7 ]

CAS No. :85-42-7MDL No. :MFCD00064863
Formula : C8H10O3 Boiling Point : 158°C at 17 mmHg
Linear Structure Formula :-InChI Key :-
M.W :154.16Pubchem ID :85689
Synonyms :

Computed Properties of [ 85-42-7 ]

TPSA : 43.4 H-Bond Acceptor Count : 3
XLogP3 : 1.2 H-Bond Donor Count : 0
SP3 : 0.75 Rotatable Bond Count : 0

Safety of [ 85-42-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H315-H317-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85-42-7 ]

  • Upstream synthesis route of [ 85-42-7 ]
  • Downstream synthetic route of [ 85-42-7 ]

[ 85-42-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 85-42-7 ]
  • [ 7506-66-3 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 11, p. 2259 - 2267
  • 2
  • [ 85-44-9 ]
  • [ 85-42-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 13, p. 2021 - 2023
[2] Patent: US2012/116099, 2012, A1, . Location in patent: Page/Page column 10
  • 3
  • [ 2426-02-0 ]
  • [ 85-42-7 ]
Reference: [1] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 1999, vol. 38, # 12, p. 1259 - 1260
[2] Gazzetta Chimica Italiana, 1909, vol. 39 II, p. 153
  • 4
  • [ 85-43-8 ]
  • [ 85-42-7 ]
Reference: [1] Patent: US2005/38283, 2005, A1, . Location in patent: Page/Page column 31
  • 5
  • [ 635-08-5 ]
  • [ 85-42-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1890, vol. 258, p. 217
[2] Justus Liebigs Annalen der Chemie, 1890, vol. 258, p. 217
  • 6
  • [ 1687-30-5 ]
  • [ 85-42-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 1999, vol. 35, # 4, p. 519 - 521
  • 7
  • [ 38765-78-5 ]
  • [ 85-42-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1909, vol. 39 II, p. 153
  • 8
  • [ 610-09-3 ]
  • [ 85-42-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1890, vol. 258, p. 217
  • 9
  • [ 85-42-7 ]
  • [ 3971-29-7 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃;
Stage #2: With water In tetrahydrofuran
A solution of hexahydrophthalic anhydride (mixture of isomers, 5.00 g, 32.0 mmol) in anhydrous tetrahydrofuran (30 mL) was added dropwise to a 0 °C cooled suspension of lithium aluminium hydride (4.21 g, 110 mol) in anhydrous tetrahydrofuran (200 mL). The reaction mixture was heated to 60 °C for 2 h. The reaction mixture was cooled to 0 °C, and crushed ice was carefully added to neutralize the excess of lithium aluminium hydride. The precipitate was filtered, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated. The crude residue was triturated in diethyl ether to give 54. Yield 75percent. 1H NMR (400 MHz, CDCl3): δ 1.36-1.55 (m, 8H), 1.91-1.96 (m, 2H), 2.76 (br s, 2H, disappeared on treatment with D2O), 3.58 (dd, J = 11.0 and 4.1 Hz, 2H), 3.77 ppm (dd, J = 11.0 and 8.2 Hz, 2H). MS (ESI): m/z: 145 [M + H]+, 167 [M + Na]+. IR: ν 3389 cm-1. Anal. Calcd. for C8H16O2: C, 66.63percent; H, 11.18percent. Found: C, 66.57percent; H, 11.16percent.
Reference: [1] Journal of Chemical Research - Part S, 2003, # 8, p. 522 - 525
[2] Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8434 - 8451
[3] Tetrahedron Letters, 2007, vol. 48, # 43, p. 7595 - 7598
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5641 - 5653
[5] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 4, p. 237 - 246
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