134155

Sigma-Aldrich

1-Methylindole-2-carboxylic acid

98%

Synonym(s):
NSC 68357
Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

mp

212-213 °C (dec.) (lit.)

SMILES string

Cn1c(cc2ccccc12)C(O)=O

InChI

1S/C10H9NO2/c1-11-8-5-3-2-4-7(8)6-9(11)10(12)13/h2-6H,1H3,(H,12,13)

InChI key

MAHAMBLNIDMREX-UHFFFAOYSA-N

General description

1-Methylindole-2-carboxylic acid reacts with thionyl chloride to yield sulfinyl chlorides.

Application

  • Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
  • Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions
  • Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes
  • Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation
  • Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications against tumor invasion and angiogenesis
  • Reactant for preparation of anthranilic acid mimics as bacterial translation inhibitors

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Reaction of Indole Derivatives with Thionyl and Sulfuryl Chlorides.
Szmuszkovicz J.
The Journal of Organic Chemistry, 29(1), 178-184 (1964)

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