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[ CAS No. 34084-89-4 ]

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2D
Chemical Structure| 34084-89-4
Chemical Structure| 34084-89-4
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Product Details of [ 34084-89-4 ]

CAS No. :34084-89-4MDL No. :MFCD13180959
Formula : C10H7NO4S Boiling Point : 393.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :237.23Pubchem ID :57722418
Synonyms :

Computed Properties of [ 34084-89-4 ]

TPSA : 100 H-Bond Acceptor Count : 5
XLogP3 : 3 H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 2

Safety of [ 34084-89-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 34084-89-4 ]

  • Upstream synthesis route of [ 34084-89-4 ]
  • Downstream synthetic route of [ 34084-89-4 ]

[ 34084-89-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 58755-57-0 ]
  • [ 2365-48-2 ]
  • [ 34084-89-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 17, p. 4016 - 4026
[2] Patent: US2003/225053, 2003, A1, . Location in patent: Page 24
  • 2
  • [ 34084-89-4 ]
  • [ 616238-78-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogenchloride; acetic acid; tin(ll) chloride In water at 20℃; for 12 h;
Stage #2: With sodium hydrogencarbonate In water at 0℃;
To a mixture of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (100 mg) in acetic acid (4 mL) was added a solution of SnC2.2H2O (10 eq) in 1.5 mL of concentrated HCl.
The reaction was stirred at room temperature 12 h.
The excess acid was partially removed in vacuo, and the reaction mixture was then poured into a flask (250 mL) and was neutralized with saturated NaHCO3 solution at 0° C.
The pH was brought up to pH 9 by adding solid NaHCO3.
The resulting aqueous mixture was diluted with EtOAc, and the Tin-by product was removed by filtering through a pad of diatomaceous earth.
The pad was rinsed with EtOAc and the combined filtrates were partitioned in a separatory funnel.
The aqueous layer was extracted with EtOAc two times times.
The combined organics were dried over MgSO4, filtered and concentrated to give the desired 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (100percent).
To a mixture of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (100 mg) in acetic acid (4 mL) was added a solution of SnCl2.2H2O (10 eq) in 1.5 mL of concentrated HCl. The reaction was stirred at room temperature 12 h. The excess acid was partially removed in vacuo, and the reaction mixture was then poured into a flask (250 mL) and was neutralized with saturated NaHCO3 solution at 0° C. The pH was brought up to pH 9 by adding solid NaHCO3. The resulting aqueous mixture was diluted with EtOAc, and the Tin-by product was removed by filtering through a pad of diatomaceous earth. The pad was rinsed with EtOAc and the combined filtrates were partitioned in a separatory funnel. The aqueous layer was extracted with EtOAc two times times. The combined organics were dried over MgSO4, filtered and concentrated to give the desired 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (100percent).
100% With hydrogen In ethyl acetate at 20℃; for 12 h; 7-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1 g, 4.22 mmol) was suspended in EtOAc (40 mL) and a suspension of 10percent Pd/C (400 mg) in 20 mL EtOAc was added.
Hydrogen gas was introduced into the flask from an H2-filled balloon attached to a needle inserted through a septum.
The black suspension was stirred 12 h at room temperature.
After stirring 12 h, the black suspension was filtered through diatomaceous earth and the filter cake was washed several times with EtOAc.
The combined filtrates were dried (MgSO4), filtered and the solvent was removed to afford 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester as a yellow solid (860 mg, 100percent).
Reference: [1] Patent: US2003/225053, 2003, A1, . Location in patent: Page 27, 35, 36
[2] Patent: US2003/225053, 2003, A1, . Location in patent: Page 28
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 17, p. 4016 - 4026
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