All Photos(1)
Synonym(s):
5-Methylindole-2-carboxylic acid ethyl ester, NSC 30928
Empirical Formula (Hill Notation):
C12H13NO2
CAS Number:
Molecular Weight:
203.24
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
Related Categories
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
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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 with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.
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