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663190

Sigma-Aldrich

Ethyl 5-methylindole-2-carboxylate

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H13NO2
CAS Number:
16382-15-3
Molecular Weight:
203.24
MDL number:
MFCD00022703
UNSPSC Code:
12352100
PubChem Substance ID:
24884618
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

160-164 °C

functional group

ester

SMILES string

CCOC(=O)c1cc2cc(C)ccc2[nH]1

InChI

1S/C12H13NO2/c1-3-15-12(14)11-7-9-6-8(2)4-5-10(9)13-11/h4-7,13H,3H2,1-2H3

InChI key

KMVFKXFOPNKHEM-UHFFFAOYSA-N

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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ8703
MKBV2518V
MKBQ9867V
MKBK1387V
MKBH0041V

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Substituent Effects in the Fischer Indolization of (2-Sulfonyloxyphenyl) hydrazones (Fischer Indolization and Related Compounds. XXX).
Murakami Y, et al.
Chemical & Pharmaceutical Bulletin, 47, 791-797 (1999)

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 monoacylated products.

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