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511129

Sigma-Aldrich

1-Methylindole-2-carboxaldehyde

97%

Synonym(s):

2-Formyl-1-methylindole, NSC 106285

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About This Item

Empirical Formula (Hill Notation):
C10H9NO
CAS Number:
27421-51-8
Molecular Weight:
159.18
MDL number:
MFCD01863665
UNSPSC Code:
12352100
PubChem Substance ID:
24873423
NACRES:
NA.22

Quality Level

100

assay

97%

mp

81-85 °C (lit.)

SMILES string

Cn1c(C=O)cc2ccccc12

InChI

1S/C10H9NO/c1-11-9(7-12)6-8-4-2-3-5-10(8)11/h2-7H,1H3

InChI key

IBNGPIOSWCMJGG-UHFFFAOYSA-N

Related Categories

Application

1-Methylindole-2-carboxaldehyde may be used in the synthesis of indole-based melatonin analog hydrazone derivatives and (E)-5-((benzyloxy)methyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-((1-methyl-1H-indol-2-yl)methylene)dihydrofuran-2(3H)-one.
Reactant for preparation of:
  • Deazapurine isosteres from acylindoles via pyridine ring annulation
  • 2,4-dichlorocinnamohydroxamic acid analogs for enhancing pharmacokinetics of botulinum neurotoxin serotype A protease inhibitors
  • Tetrahydrocarbazoles via organocatalytic cascade Friedel-Crafts alkylation/Michael addition/aromatization reaction
  • Azides, imines and amines via flow processes of amines and trimethylsilyl azide and aza-Wittig reaction
  • 3-indolylpyridinedicarbonitriles as anti-inflammatory agents
  • Bis(indolyl)methanes as antimicrobial and antioxidant agents

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Noga Gal et al.
Chembiochem : a European journal of chemical biology, 12(15), 2331-2340 (2012-10-30)
N-methyl-substituted diacylglycerol-indololactones (DAG-indololactones) are newly synthesized effectors of protein kinase C (PKC) isoforms and exhibit substantial selectivity between RasGRP3 and PKCα. We present a comprehensive analysis of membrane interactions and biological activities of several DAG-indololactones. Translocation and binding activity assays
Sibel Suzen et al.
Journal of enzyme inhibition and medicinal chemistry, 28(6), 1143-1155 (2012-09-22)
Melatonin (MLT) is a strong free-radical scavenger, which protects the body from the effects of oxidants. In recent years, MLT have been described resulting in much attention in the development of synthetic compounds possessing. As a part of our ongoing

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