METHYL 5-AMINO-1-BENZOTHIOPHENE-2-CARBOXYLATE Chemical Properties

Melting point:

178-179 ºC

Boiling point:

382.8±22.0 °C(Predicted)

Density 

1.352±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

3.52±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

HS Code 

2934999090

METHYL 5-AMINO-1-BENZOTHIOPHENE-2-CARBOXYLATE Usage And Synthesis

Definition

ChEBI: Methyl 5-amino-1-benzothiophene-2-carboxylate is a member of 1-benzothiophenes.

Synthesis

General procedure for the synthesis of methyl 5-aminobenzothiophene-2-carboxylate from methyl 5-nitrobenzo[b]thiophene-2-carboxylate: to a reaction flask was added methyl 5-nitrobenzo[b]thiophene-2-carboxylate (1 g, 0.004 mol), concentrated nitric acid (20 mL, 0.24 mol) and SnCl2-2H2O (4.85 g, 0.017 mol). The reaction mixture was stirred at 80 °C for 1 h and subsequently cooled to room temperature. The pH of the reaction mixture was adjusted with 10% aqueous sodium hydroxide solution to 9~11. The resulting suspension was filtered and the solid residue was washed with water and methanol sequentially to afford the target product, methyl 5-aminobenzothiophene-2-carboxylate, as a yellow solid in quantitative yield.

References

[1] Patent: WO2006/101454, 2006, A1. Location in patent: Page/Page column 45
[2] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 5, p. 1611 - 1618
[3] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6382 - 6394
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 9, p. 963 - 967
[5] Patent: WO2005/42513, 2005, A1. Location in patent: Page/Page column 57-58

METHYL 5-AMINO-1-BENZOTHIOPHENE-2-CARBOXYLATE(20699-85-8)Related Product Information

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• METHYL 5-([3-(TRIFLUOROMETHYL)BENZOYL]AMINO)-1-BENZOTHIOPHENE-2-CARBOXYLATE
• METHYL 5-[(4-FLUOROBENZOYL)AMINO]-1-BENZOTHIOPHENE-2-CARBOXYLATE
• METHYL 3-((4,4-DIMETHYL-2,6-DIOXO(3,5-DIOXANYL))DIAZENYL)-5-NITROBENZO[B]THIOPHENE-2-CARBOXYLATE
• METHYL 5-([(2,4,5-TRICHLOROPHENYL)SULFONYL]AMINO)-1-BENZOTHIOPHENE-2-CARBOXYLATE
• METHYL 5-[(3-CHLOROBENZOYL)AMINO]-1-BENZOTHIOPHENE-2-CARBOXYLATE
• METHYL 5-[(PHENYLSULFONYL)AMINO]-1-BENZOTHIOPHENE-2-CARBOXYLATE