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663190 Sigma-Aldrich

Ethyl 5-methylindole-2-carboxylate

97%

Synonym: 5-Methylindole-2-carboxylic acid ethyl ester, NSC 30928

  • CAS Number 16382-15-3

  • Empirical Formula (Hill Notation) C12H13NO2

  • Molecular Weight 203.24

  •  MDL number MFCD00022703

  •  PubChem Substance ID 24884618

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C12, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
InChI Key   KMVFKXFOPNKHEM-UHFFFAOYSA-N
assay   97%
mp   160-164 °C

Description

General description

Ethyl 5-methylindole-2-carboxylate (5-Methylindole-2-carboxylic acid ethyl ester) is an indole derivative. Indole ring system is an important building block or intermediate in the synthesis of many pharmaceutical agents. It is formed during the Fischer indolization of ethyl pyruvate 2-[2-(methanesulfonyloxy)-4-methyl]phenylhydrazine.

Application

• Reactant for synthesis of oxazino[4,3-a]indoles via cascade addition-cyclization reactions
• Reactant for preparation of indolecarboxamides as cannabinoid CB1 receptor antagonists
• Reactant for preparation of indole-3-propionic acids as antiinflammatory and analgesic agents
• Reactant for Friedel-Crafts acylation with nitrobenzoyl chloride
• Reactant for oximation reactions

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form m...
Keywords: Acylations, Catalysis, Electrophilic aromatic substitution, Microwave synthesis, Substitutions

Peer-Reviewed Papers
15

References

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