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Sigma-Aldrich

1-Methyl-2-phenylindole

99%

Synonym(s):

NSC 63793

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About This Item

Empirical Formula (Hill Notation):
C15H13N
CAS Number:
3558-24-5
Molecular Weight:
207.27
EC Number:
222-618-1
MDL number:
MFCD00022892
UNSPSC Code:
12352100
PubChem Substance ID:
24865277
NACRES:
NA.22

Quality Level

100

Assay

99%

mp

98-100 °C (lit.)

SMILES string

Cn1c(cc2ccccc12)-c3ccccc3

InChI

1S/C15H13N/c1-16-14-10-6-5-9-13(14)11-15(16)12-7-3-2-4-8-12/h2-11H,1H3

InChI key

SFWZZSXCWQTORH-UHFFFAOYSA-N

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General description

Reaction of 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene has been studied. 1-Methyl-2-phenylindole is reported to react with malondialdehyde (MDA) and 4-hydroxyalkenals to afford a stable chromophore with intense maximal absorbance at 586nm.

Application

1-Methyl-2-phenylindole may be used in the following studies:
  • The estimation of lipid peroxidation in third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ)Bg.
  • As chromogenic agent for the determination of estimation of malondialdehyde (MDA) production.
  • Colorimetric assay of lipid peroxidation.
  • Synthesis of 1-methyl-2-phenyl-3-(1,3,4-thiadiazol-2-yldiazenyl)-1H-indole.
  • Synthesis of 3-(5-ethyl-1,3,4-thiadiazol-2-yldiazenyl)-1-methyl-2-phenyl-1H-indole.
Reactant for preparation of:
  • Cyano indoles
  • Difluorohydroxy indoles

Reactant for:
  • Carboxylation of indoles
  • Allylation of indoles
  • Formylation of indoles
  • Nitrosylation of indoles

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1-Methyl-2-phenyl-3-(1, 3, 4-thiadiazol-2-yldiazenyl)-1H-indole.
Seferoglu Z, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(1), 148-150 (2007)
M Olleros Santos-Ruiz et al.
Growth hormone & IGF research : official journal of the Growth Hormone Research Society and the International IGF Research Society, 35, 21-32 (2017-06-27)
We previously described in cirrhosis and aging, both conditions of IGF-1 deficiency, a clear hepatic mitochondrial dysfunction with increased oxidative damage. In both conditions, the hepatic mitochondrial function was improved with low doses of IGF-1. The aim of this work
Jan Bilski et al.
Nutrients, 11(5) (2019-05-24)
Inflammatory bowel diseases are a heterogeneous group of disorders represented by two major phenotypic forms, Crohn's disease and ulcerative colitis. Cross talk between adipokines and myokines, as well as changes in intestinal microcirculation, was proposed in pathogenesis of these disorders.
Yasir Hasan Siddique et al.
Dose-response : a publication of International Hormesis Society, 10(1), 1-10 (2012-03-17)
Malondialdehyde (MDA) is used for the estimation of damage by reactive oxygen species. MDA is a major reactive aldehyde resulting from the peroxidation of biological membranes. The most common method used to assess MDA production is the thiobarbituric acid (TBARS)
Yasir Hasan Siddique et al.
Pharmaceutical methods, 3(2), 94-97 (2013-06-20)
A method using 1-methyl-2-phenylindole was developed for the estimation of lipid peroxidation in third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ)Bg (9). The method is specific for the estimation of malonaldehyde. The larvae were exposed to 0.0025, 0.025, 0.050, and
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