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Sigma-Aldrich

Methyl 3-amino-2-thiophenecarboxylate

99%

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Empirical Formula (Hill Notation):
C6H7NO2S
CAS Number:
22288-78-4
Molecular Weight:
157.19
EC Number:
244-895-8
MDL number:
MFCD00009765
PubChem Substance ID:
24853938
NACRES:
NA.22

Assay

99%

form

solid

bp

100-102 °C/0.1 mmHg (lit.)

mp

62-64 °C (lit.)

SMILES string

COC(=O)c1sccc1N

InChI

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

InChI key

TWEQNZZOOFKOER-UHFFFAOYSA-N

Related Categories

General description

Methyl 3-amino-2-thiophenecarboxylate reacts with hydrazonoyl chlorides in the presence of triethylamine to yield corresponding N-arylamidrazones.

Application

Methyl 3-amino-2-thiophenecarboxylate was used in:
  • the synthesis of 4-nitro and 4-aminothienyl ureas
  • total synthesis of quinazolinocarboline alkaloids
  • preparation of thienopyrimidinone analogs

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1, 2, 3-dithiazol-5-ylidene) anthranilates.
Mohanta PK and Kim K.
Tetrahedron Letters, 43(22), 3993-3996 (2002)
Synthesis and Properties of Some New 1, 4-Dihydrothieno [3, 2-e][1, 2, 4] triazepin-5-ones.
Sabri SS, et al.
Zeitschrift fur Naturforschung, B: Chemical Sciences, 61(1), 65-65 (2006)
Donald L Hertzog et al.
Bioorganic & medicinal chemistry letters, 16(18), 4723-4727 (2006-07-28)
Optimization of a series of constrained melanin-concentrating hormone receptor 1 (MCH R1) antagonists has provided compounds with potent and selective MCH R1 activity. Details of the optimization process are provided and the use of one of the compounds in an
A M Redman et al.
Bioorganic & medicinal chemistry letters, 11(1), 9-12 (2001-01-05)
Inhibitors of the MAP kinase p38 are potentially useful for the treatment for osteoporosis, arthritis, and other inflammatory diseases. A series of thienyl, furyl, and pyrrolyl ureas has been identified as potent p38 inhibitors, displaying in vitro activity in the

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