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[ CAS No. 55076-32-9 ]

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2D
Chemical Structure| 55076-32-9
Chemical Structure| 55076-32-9
Structure of 55076-32-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 55076-32-9 ]

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Product Details of [ 55076-32-9 ]

CAS No. :55076-32-9MDL No. :MFCD00463877
Formula : C8H7NO5 Boiling Point : 377.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :197.15Pubchem ID :239344
Synonyms :

Computed Properties of [ 55076-32-9 ]

TPSA : 92.4 H-Bond Acceptor Count : 5
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 2

Safety of [ 55076-32-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55076-32-9 ]

  • Upstream synthesis route of [ 55076-32-9 ]

[ 55076-32-9 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
87% at 80℃; for 18.00 h; Large scale In 3-hydroxy-5-nitrobenzoic acid (5.9 kg, 32.2 mol), methanol (60 L) was added, and sulfuric acid (375 ml, catalytic amount) was slowly added thereto, followed by refluxing and stirring at 80° C. for 18 hours.
After completing the reaction, the reactant was cooled to room temperature.
Purified water (50 L) was added thereto, and methanol was distilled off under a reduced pressure.
The solid thus produced was stirred at 10° C. for 1 hour and filtered.
The filtrant was washed with purified water, and dried at 60° C. to obtain the title compound (5.52 kg, yield: 87percent, yellow solid).
1H-NMR (400 MHz, DMSO-d6) δ 10.91 (s, 1H), 8.04 (s, 1H), 7.74 (s, 1H), 7.66 (s, 1H), 3.88 (s, 3H)
3.9 g at 0 - 6℃; for 3.00 h; o a solution of 3-hydroxy-5-nitrobenzoic acid (3.7 g, 20.00 mmol) in MeOH (70.0 mL), SOCl2(12.0 mL) was added at 0°C. The reaction mixture was stirred at 6°C for 3 hours, and concentrated under reduced pressure. Water was added to the residue, followed by extracting with EtOAc. The organic extract was washed with brine, dried over anhydrous Na2S04, concentrated under reduced pressure to obtain methyl 3-hydroxy- 5-nitrobenzoate (3.9 g) as an off-white solid without purification.1H-NMR (300MHz, DMSO-d6) δ 10.96 (s, 1H), 8.08 (m, 1H), 7.78 (m, 1H), 7.70 (m, 1H), 3.90 (s, 3H)
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4812 - 4830
[2] Patent: US2014/350007, 2014, A1. Location in patent: Paragraph 0076; 0077; 0078
[3] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1549 - 1559
[4] Patent: US2010/69431, 2010, A1. Location in patent: Page/Page column 110-111
[5] Patent: WO2014/196793, 2014, A1. Location in patent: Page/Page column 74
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7821 - 7825[7] Angew. Chem., 2016, vol. 128, p. 7952 - 7956,5
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YieldReaction ConditionsOperation in experiment
100% With Oxone; sodium hydrogencarbonate; sodium hydroxide In water; acetone at 8℃; for 0.08 h; 3-Nitro-5-methoxycarbonylphenylboronic acid (225 mg, 1.0 mmol) was added to a vigorously stirred solution of sodium hydroxide (59 mg, 1.5 mmol) in water (15 mL), followed by sodium bicarbonate (681 mg, 8.1 mmol) and acetone (1 mL). Oxone.(R). (543 mg, 0.88 mmol) was added slowly, keeping the temperature below 8° C. The reaction mixture was stirred 5 min and quenched with sodium bisulfite (600 mg). The reaction mixture was diluted with ethyl acetate and carefully acidified with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate (3.x.) and the combined organic layers were washed with water and brine and concentrated in vacuo to give 93A (258 mg, 100percent) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm 3.95 (s, 3H) 7.74-7.78 (m, 1H) 7.78-7.83 (m, 1H) 8.23-8.28 (m, 1H); LC/MS 198 (M+H).
Reference: [1] Patent: US2010/227894, 2010, A1. Location in patent: Page/Page column 73
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  • [ 78238-14-9 ]
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Reference: [1] Patent: US2002/165275, 2002, A1
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  • [ 618-84-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1549 - 1559
  • 5
  • [ 99-34-3 ]
  • [ 55076-32-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1549 - 1559
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