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Sigma-Aldrich

Methyl 3-amino-2-thiophenecarboxylate

99%

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About This Item

Empirical Formula (Hill Notation):
C6H7NO2S
CAS Number:
22288-78-4
Molecular Weight:
157.19
EC Number:
244-895-8
MDL number:
MFCD00009765
UNSPSC Code:
12352100
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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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

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