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Key Documents

M51407

Sigma-Aldrich

2-Methylindole

98%

Synonym(s):

NSC 7514

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About This Item

Empirical Formula (Hill Notation):
C9H9N
CAS Number:
Molecular Weight:
131.17
Beilstein:
109781
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

bp

273 °C (lit.)

mp

57-59 °C (lit.)

SMILES string

Cc1cc2ccccc2[nH]1

InChI

1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3

InChI key

BHNHHSOHWZKFOX-UHFFFAOYSA-N

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Application

Reactant for:
  • Regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction
  • Friedel-Crafts alkylation reactions
  • Preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Preparation of plant-growth inhibitors
  • Michael addition reactions
  • Synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

285.8 °F

Flash Point(C)

141 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J M Gutteridge
The International journal of biochemistry, 14(7), 649-653 (1982-01-01)
1. The thiobarbituric acid (TBA) reaction, widely applied to the detection of autoxidation in polyunsaturated fatty acids, can be used to measure free-radical damage to amino acids, carbohydrates and nucleic acids. 2. In all of these systems malondialdehyde (MDA) is
V F Ximenes et al.
Archives of biochemistry and biophysics, 387(2), 173-179 (2001-05-24)
The indole moeity is present in many substances of biological occurrence. Its metabolism, in most cases, involves an oxidative pathway. This study reports the oxidation of a series of indole derivatives, including several of biological origin, catalyzed by horseradish peroxidase
[2-Methylindoles substituted in the 1st, 3d and 5th positions and the diffuse neuroendocrine APUD system].
K S Shadurskiĭ et al.
Farmakologiia i toksikologiia, 46(2), 115-120 (1983-03-01)
Nevin Erciyes et al.
Journal of colloid and interface science, 278(1), 91-95 (2004-08-18)
The adsorption of indole and its 2-methyl derivative from aqueous solutions onto cobalt(II)-carboxylated diaminoethane sporopollenin (CDAE-sporopollenin) was studied using a fixed-bed column at 25+/-0.1 degrees C. Minicolumn adsorption studies showed that the breakthrough and the total adsorption capacities of CDAE-sporopollenin
T Bhattacharya et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 60(8-9), 1957-1966 (2004-07-14)
Electrochemical measurements by cyclic voltammetry predict the possibility of occurrence of photoinduced electron-transfer (PET) reactions between the ground state of 2-phenylindole (2PI) (electron donor) and the excited singlet of 9-cyanoanthracene (9CNA) molecule acting as an electron acceptor. However, 2PI should

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