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134155

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
NACRES:
NA.22
PubChem Substance ID:
24848134
UNSPSC Code:
12352100
MDL number:
MFCD00005801
Assay:
98%
Form:
powder
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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL8247
36696EM
02030PH
S44247
S08818

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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)

Global Trade Item Number

SKUGTIN
345830-5ML04061826760888
345830-25ML04061837083303
134155-5G04061832841533
134155-1G04061826135488