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14597-58-1

14597-58-1 Structure

14597-58-1 Structure
IdentificationBack Directory
[Name]

5-Amino-thiophene-2-carboxylic acid methyl ester
[CAS]

14597-58-1
[Synonyms]

5-aminothiophene-2-carboxylic methyl ester
5-Amino-thiophene-2-carboxylic acid methyl ester
2-Thiophenecarboxylicacid, 5-aMino-, Methyl ester
[EINECS(EC#)]

200-110-4
[Molecular Formula]

C6H7NO2S
[MDL Number]

MFCD07687259
[MOL File]

14597-58-1.mol
[Molecular Weight]

157.19
Chemical PropertiesBack Directory
[Melting point ]

81 °C
[Boiling point ]

304.8±22.0 °C(Predicted)
[density ]

1.319±0.06 g/cm3(Predicted)
[storage temp. ]

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

0.38±0.10(Predicted)
[Appearance]

Light brown to brown Solid
[InChI]

InChI=1S/C6H7NO2S/c1-9-6(8)4-2-3-5(7)10-4/h2-3H,7H2,1H3
[InChIKey]

NNQTUMGJWXJMIR-UHFFFAOYSA-N
[SMILES]

C1(C(OC)=O)SC(N)=CC=1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Health Hazard (GHS08)
GHS07,GHS08
[Signal word ]

Danger
[Hazard statements ]

H302-H312-H315-H319-H332-H334-H335
[Precautionary statements ]

P261-P280-P305+P351+P338-P342+P311
Spectrum DetailBack Directory
[Spectrum Detail]

5-Amino-thiophene-2-carboxylic acid methyl ester(14597-58-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

5-NITROTHIOPHENE-2-CARBOXYLICMETHYLESTER

5832-01-9

5-Amino-thiophene-2-carboxylic acid methyl ester

14597-58-1

General procedure for the synthesis of methyl 5-amino-2-thiophenecarboxylate from methyl 5-nitro-2-thiophenecarboxylate: Methyl 5-nitro-2-thiophenecarboxylate (11.55 mmol) was dissolved in ethanol (20 mL), and 10% palladium carbon catalyst (1 g) was added. The reaction mixture was hydrogenated overnight with stirring under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was subsequently concentrated to afford the target product methyl 5-amino-2-thiophenecarboxylate (1.67 g, 92% yield). The product was detected by LCMS (ESI) and showed a molecular ion peak of 157 [M+H]+.

[References]

[1] Patent: WO2006/65788, 2006, A2. Location in patent: Page/Page column 10
[2] Patent: US2007/43045, 2007, A1. Location in patent: Page/Page column 59
[3] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382
[4] Patent: WO2004/108683, 2004, A1. Location in patent: Page 564-565
[5] Patent: WO2004/18480, 2004, A1. Location in patent: Page 156
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