| Identification | More | [Name]
Methyl 2-aminothiophene-3-carboxylate | [CAS]
4651-81-4 | [Synonyms]
2-AMINO-3-METHOXYCARBONYLTHIOPHENE
AKOS 90546
AKOS B014692
ART-CHEM-BB B014692
BUTTPARK 46\18-81
methyl 2-amino-3-thenoate
METHYL 2-AMINO-3-THIOPHENECARBOXYLATE
METHYL 2-AMINOTHIOPHENE-3-CARBOXYLATE
METHYL 2-AMINOTHIOPHENE-3-CARBOXYLAT&
2-Amino-3-thiophenecarboxylic acid methyl ester | [EINECS(EC#)]
225-084-8 | [Molecular Formula]
C6H7NO2S | [MDL Number]
MFCD00159547 | [Molecular Weight]
157.19 | [MOL File]
4651-81-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
76-81 °C (lit.) | [Boiling point ]
259.5±20.0 °C(Predicted) | [density ]
1.319±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
solid | [pka]
0.10±0.10(Predicted) | [color ]
Beige | [Detection Methods]
GC | [InChI]
InChI=1S/C6H7NO2S/c1-9-6(8)4-2-3-10-5(4)7/h2-3H,7H2,1H3 | [InChIKey]
DGGJQLCAYQCPDD-UHFFFAOYSA-N | [SMILES]
C1(N)SC=CC=1C(OC)=O | [CAS DataBase Reference]
4651-81-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
Methyl 2-aminothiophene-3-carboxylate may be used to prepare 3-thiaisatoic anhydride via hydrolysis, followed by the reaction with phosgene. | [Uses]
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. | [Definition]
ChEBI: Methyl 2-aminothiophene-3-carboxylate is a thiophenecarboxylic acid. | [Synthesis]
To two 20 mL microwave reaction tubes were added 1,4-dithio-2,5-diol (2.0 g, 13.1 mmol, 1.0 eq.) and methanol (10.5 mL), respectively, and the reaction tubes were sealed. Methyl cyanoacetate (2.32 mL, 26.3 mmol, 2.0 eq.), triethylamine (1.28 mL, 9.20 mmol, 0.7 eq.), and N,N-dimethylformamide (3 drops) were added sequentially through the septum to each reaction tube. The reaction mixture was placed in a microwave reactor and the reaction was heated at 50 °C for 3 min. Upon completion of the reaction, the reaction solutions in the two tubes were combined and left at room temperature to allow the product to precipitate. The precipitate was collected by filtration and washed with cold methanol to afford methyl 2-aminothiophene-3-carboxylate (16as) as a white solid (3.88 g, 24.7 mmol, 94% yield). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[2] Patent: WO2015/959, 2015, A1. Location in patent: Page/Page column 47
[3] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[4] Tetrahedron, 2012, vol. 68, # 45, p. 9226 - 9233
[5] Patent: WO2005/63734, 2005, A2. Location in patent: Page/Page column 60-61 |
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