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Sigma-Aldrich

Methyl 2-aminothiophene-3-carboxylate

97%

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About This Item

Linear Formula:
C4H2SCOOCH3NH2
CAS Number:
Molecular Weight:
157.19
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

76-81 °C (lit.)

SMILES string

COC(=O)c1ccsc1N

InChI

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

InChI key

DGGJQLCAYQCPDD-UHFFFAOYSA-N

Application

Methyl 2-aminothiophene-3-carboxylate may be used to prepare 3-thiaisatoic anhydride via hydrolysis, followed by the reaction with phosgene.
Methyl 2-aminothiophene-3-carboxylate may be used to synthesize the following:
  • thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
  • thieno[2,3-d]pyrimidin-4(3H)one via reaction with formamide
  • methyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)thiophene-3-carboxylate via reaction with hexane-2,5-dione


Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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"Synthesis of novel 5-chlorinated 2-aminothiophenes using 2, 5-dimethylpyrrole as an amine protecting group"
Puterova Z, et al.
Journal of Heterocyclic Chemistry, 45(1), 201-207 (2008)
?Synthesis, immunosuppressive activity and structure?activity relationship study of a new series of 4-N-piperazinyl-thieno [2, 3-d] pyrimidine analogues"
Jang Y-M, et al.
Bioorganic & Medicinal Chemistry Letters, 20(3), 844-847 (2010)
"The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes"
Deng J, et al.
European Journal of Medicinal Chemistry, 46(1), 71- 76 (2011)
"Chemistry of Ring-Fused Oxazine-2, 4-diones"
lette Y, et al. et al.
European Journal of Organic Chemistry, 2009(21), 3487-3503 (2009)
"Design, synthesis and biological evaluation of 4-anilinothieno [2, 3-d] pyrimidine-based hydroxamic acid derivatives as novel histone deacetylase inhibitors"
Zhu W, et al.
Bioorganic & Medicinal Chemistry, 22(21), 6146-6155 (2014)

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