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[ CAS No. 87-41-2 ]

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2D
Chemical Structure| 87-41-2
Chemical Structure| 87-41-2
Structure of 87-41-2 *Storage: {[proInfo.prStorage]}

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Product Details of [ 87-41-2 ]

CAS No. :87-41-2MDL No. :MFCD00005906
Formula : C8H6O2 Boiling Point : 290°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :134.13Pubchem ID :6885
Synonyms :

Computed Properties of [ 87-41-2 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 0

Safety of [ 87-41-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 87-41-2 ]

  • Upstream synthesis route of [ 87-41-2 ]
  • Downstream synthetic route of [ 87-41-2 ]

[ 87-41-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 87-41-2 ]
  • [ 102308-43-0 ]
Reference: [1] Bulletin de la Societe Scientifique de Bretagne, 1951, vol. 26, p. Sonderheft 5, S. 7, 96[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1952, vol. 235, p. 962
  • 2
  • [ 87-41-2 ]
  • [ 19477-73-7 ]
YieldReaction ConditionsOperation in experiment
66% at 20℃; for 69 h; NBS (53.4 g, 300 mmol, 1.5 eq) was added portion wise to a solution of phthalide (Sl-I) (26.83 g, 200 mmol. 1 O eq) in a mixture of TFA (100 mL) and sulfuric acid (45 mL) at rt over 9 h. The reaction mixture (an orange solution) was stirred at rt for about 60 h. (Crude NMR showed the reaction is complete.) Then the reaction mixture was poured onto ice, extracted with methylene chloride (3 x 300 mL). The combined organic phase was dried over MgSO4, filtered and concentrated to afford a yellow solid. The residue was purified by flash-column chromatography (5-10percent ethyl acetate-hexanes) to afford the desired product Sl-2 (white solid, 28.17g, 66percent) and the other regioisomer S3-1 (white solid, 12.7g, 30percent). 1H NMR (400 MHz, CDCl3) 8 8.04 (d, J= 1.8 Hz, 1 H), 7.78 (dd, J= 1.8, 7.9 Hz, 1 H), 7.37 (d, J= 7.9 Hz, 1 H), 5.26 (s, 2 H).
57% With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid In ethyl acetate for 95 h; 6-Bromoisobenzofuran-1(3H)-one (20a) In a 100 mL round bottom flask was dissolved isobenzofuran-1(3H)-one (4.01 g, 29.9 mmol) in trifluoroacetic acid (14 mL, 182 mmol) and sulfuric acid (6.5 mL, 122 mmol). N-Bromosuccinimide (7.95 g, 1.49 mmol) was added portionwise over 8 hours and the solution was stirred at room temperature for an additional 87 hours.
The solution was diluted with water (40 mL) and ethyl acetate (40 mL).
The pH of the aqueous layer was neutralized with 1M aq. NaOH and sat. aq. NaHCO3.
The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3*50 mL).
The combined organic layers were washed with brine (25 mL), dried over Na2SO4, and concentrated on to silica.
The crude product was then purified by flash column chromatography using 10-20percent ethyl acetate in hexanes to yield 20a as white solid in 57percent yield. 1H NMR (500 MHz, CDCl3) δ 7.98 (d, J=1.5 Hz, 1H), 7.77 (dd, J=8.3, 1.5 Hz, 1H), 7.40 (d, J=8.3 Hz, 1H), 5.27 (s, 2H). LCMS found 212.9 [M+H]+.
Reference: [1] Patent: WO2010/132670, 2010, A2, . Location in patent: Page/Page column 50-51
[2] Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9085 - 9088
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[4] Patent: US2015/259331, 2015, A1, . Location in patent: Paragraph 0195
[5] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[6] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
[7] Patent: US2011/98311, 2011, A1,
[8] Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751
[9] Tetrahedron, 2013, vol. 69, # 15, p. 3287 - 3292
[10] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[11] Patent: US2015/231142, 2015, A1,
[12] Patent: CN105153013, 2017, B,
  • 3
  • [ 87-41-2 ]
  • [ 64169-34-2 ]
  • [ 19477-73-7 ]
Reference: [1] Patent: CN105153013, 2017, B, . Location in patent: Paragraph 0045-0050
  • 4
  • [ 87-41-2 ]
  • [ 107558-48-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 12, p. 2310 - 2323
[2] Chinese Chemical Letters, 2010, vol. 21, # 9, p. 1071 - 1074
[3] Archiv der Pharmazie, 2012, vol. 345, # 4, p. 287 - 293
  • 5
  • [ 87-41-2 ]
  • [ 1229-29-4 ]
Reference: [1] Patent: CN105418577, 2016, A,
[2] Patent: CN105418577, 2016, A,
[3] Patent: CN105418577, 2016, A,
  • 6
  • [ 87-41-2 ]
  • [ 152265-57-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Patent: US2015/259331, 2015, A1,
  • 7
  • [ 87-41-2 ]
  • [ 1016163-89-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751
[2] Tetrahedron, 2013, vol. 69, # 15, p. 3287 - 3292
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