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134155

Sigma-Aldrich

1-Methylindole-2-carboxylic acid

98%

Synonym(s):

NSC 68357

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
16136-58-6
Molecular Weight:
175.18
MDL number:
MFCD00005801
UNSPSC Code:
12352100
PubChem Substance ID:
24848134
NACRES:
NA.22

Assay

98%

form

powder

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

134155-BULK:
134155-250G:
134155-500G:
134155-5G:
134155-VAR:
134155-1G:
134155-25G:

Certificates of Analysis (COA)

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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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