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Ethyl 5-methylindole-2-carboxylate

Name: Ethyl 5-methylindole-2-carboxylate
Brand: ALDRICH

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

assay

97%

form

solid

mp

160-164 °C

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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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