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[ CAS No. 27550-59-0 ]

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2D
Chemical Structure| 27550-59-0
Chemical Structure| 27550-59-0
Structure of 27550-59-0 *Storage: {[proInfo.prStorage]}

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Product Details of [ 27550-59-0 ]

CAS No. :27550-59-0MDL No. :MFCD00997252
Formula : C8H4O4 Boiling Point : 407.8±28.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :164.12Pubchem ID :639747
Synonyms :

Computed Properties of [ 27550-59-0 ]

TPSA : 63.6 H-Bond Acceptor Count : 4
XLogP3 : 0.9 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 27550-59-0 ]

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 [ 27550-59-0 ]

  • Upstream synthesis route of [ 27550-59-0 ]
  • Downstream synthetic route of [ 27550-59-0 ]

[ 27550-59-0 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
97% at 210℃; Green chemistry (3) 12.3 g (67.5 mmol) of 4-hydroxyphthalic acid was placed in a sublimation tube and sublimed at 210 ° C to give 10.8 g of 4-hydroxyphthalic anhydride as a pale yellow solid in 97percent yield.
74.9% at 220℃; 4-Hydroxyphthalic acid (1 g, 5.49 mmol) was sublimated at 220° C. under vacuum (about 10 mbar). The obtained white solid 5-hydroxyisobenzofuran-1,3-dione (675 mg, 4.11 mmol, 74.9percent yield, MS/ESI164.9 [MH]+) was collected, stored under vacuum and used as such in the next step.
74.9% at 220℃; Example 45 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy) phenyl)-2-(2-(1 ,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetoxy)ethyl) pyridine 1 -oxide 2,2,2-trifluoroacetic acid salt (Compound 248) Scheme 45 Step 1 : Preparation of 5-hydroxyisobenzofuran-1 ,3-dione (244): 4-Hydroxyphthalic acid (1 g, 5.49 mmol) was sublimated at 220°C under vacuum (about 10 mbar). The obtained white solid 5-hydroxyisobenzofuran-1 ,3- dione (675 mg, 4.1 1 mmol, 74.9percent yield, MS/ESI+ 164.9 [MH] +) was collected, stored under vacuum and used as such in the next step.
74% at 200℃; for 1.00 h; 2nd Stage:
4-hydroxyphthalic anhydride
4-hydroxyphthalic acid (23.80 g, 0.131 mol) was heated for 1 h in an oil bath preheated to 200° C.
After cooling the brownish solid was recrystallized from ethyl acetate/n-hexane (1:1).
15.82 g (96.4 mmol; 74percent yield) of a white solid was obtained.
1H-NMR (DMSO-d6, 400 MHz): δ=7.25 (d, 1H; J=2.0 Hz), 7.28 (dd, 1H; J=2.0 Hz, 8.5 Hz), 7.89 (d, 2H, J=8.0 Hz), 11.44 (br s, 1H).
13C-NMR (DMSO-d6, 100 MHz): δ=111.0, 120.7, 123.0, 127.6, 133.9, 162.7, 163.2, 164.8.
74% at 200℃; for 1.00 h; 2nd Stage:
4-hydroxyphthalic anhydride
4-hydroxyphthalic acid (23.80 g, 0.131 mol) was heated for 1 h in an oil bath preheated to 200° C.
After cooling the brownish solid was recrystallized from ethyl acetate/n-hexane (1:1).
15.82 g (96.4 mmol; 74percent yield) of a white solid was obtained.
1H-NMR (DMSO-d6, 400 MHz): δ=7.25 (d, 1H; J=2.0 Hz), 7.28 (dd, 1H; J=2.0 Hz, 8.5 Hz), 7.89 (d, 2H, J=8.0 Hz), 11.44 (br s, 1H).
13C-NMR (DMSO-d6, 100 MHz): δ=111.0, 120.7, 123.0, 127.6, 133.9, 162.7, 163.2, 164.8.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4427 - 4431
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 342 - 353
[3] Patent: CN104910113, 2017, B. Location in patent: Page/Page column 0041; 0044-0046
[4] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[5] Patent: US2013/102576, 2013, A1. Location in patent: Paragraph 0607
[6] Patent: WO2013/57013, 2013, A2. Location in patent: Page/Page column 193
[7] Patent: US2013/90404, 2013, A1. Location in patent: Paragraph 0075; 0076; 0077; 0078
[8] Patent: US9393181, 2016, B2. Location in patent: Page/Page column 9
[9] Monatshefte fuer Chemie, 1902, vol. 23, p. 401
[10] Journal of the Chemical Society, 1907, vol. 91, p. 103
[11] Chemische Berichte, 1877, vol. 10, p. 1079
[12] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[13] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 5, p. 1249 - 1256
[14] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 283 - 287
[15] Patent: EP1681283, 2006, A1. Location in patent: Page/Page column 4-5
[16] Synthesis, 2008, # 21, p. 3415 - 3422
[17] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5323 - 5338
[18] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[19] Marine Drugs, 2016, vol. 14, # 6,
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Reference: [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[2] Patent: CN104910113, 2017, B
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Reference: [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
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Reference: [1] Patent: US2013/90404, 2013, A1
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Reference: [1] Chemische Berichte, 1877, vol. 10, p. 1079
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Reference: [1] Chemische Berichte, 1877, vol. 10, p. 1079
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  • [ 1337915-27-1 ]
  • [ 53266-48-1 ]
  • [ 88-99-3 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 2011, vol. 63, # 9, p. 1156 - 1160
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