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Merck
CN

120812

2,3-Dimethylindole

≥97%

Synonym(s):

NSC 24936

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About This Item

Empirical Formula (Hill Notation):
C10H11N
CAS Number:
Molecular Weight:
145.20
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
202-076-2
MDL number:
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Product Name

2,3-Dimethylindole, ≥97%

InChI key

PYFVEIDRTLBMHG-UHFFFAOYSA-N

InChI

1S/C10H11N/c1-7-8(2)11-10-6-4-3-5-9(7)10/h3-6,11H,1-2H3

SMILES string

Cc1[nH]c2ccccc2c1C

assay

≥97%

form

solid

bp

285 °C (lit.)

mp

105-107 °C (lit.)

Quality Level

Application

2,3-Dimethylindole has been used to study the mechanism of oxidation of 2,3-dimethylindole by peroxodisulphate and peroxomonosulphate anions to 2-methylindole-2-carbaldehyde. It has been used to study the behaviour of methylindoles in the agilent multimode ion source by atmospheric pressure chemical ionization mass spectrometry.
Reactant for preparation of:
  • Bis(indolyl)methane derivatives
  • Potent opioid receptor agonists
  • Photorefractive materials
  • Prodrugs of the cyclin-dependent kinase (CDK) inhibitor Alsterpaullone
  • Dopamine receptors 2/4 (D2/D4) antagonists
  • Useful azaspirocyclic building blocks

Reactant for:
  • Baylis-Hillman reactions
  • Photosensitized Diels-Alder reactions
  • Photoinduced electron transfer reactions

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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A I Novaira et al.
Journal of photochemistry and photobiology. B, Biology, 60(1), 25-31 (2001-06-02)
The quenching of anthracene fluorescence by indole, 1,2-dimethylindole (DMI), tryptophan (Trp) and indole 3-acetic acid (IAA) in palmitoyloleoylphosphatidylcholine (POPC) lipid bilayers was investigated. A very efficient quenching of the anthracene fluorescence in the lipid membrane is observed. Stern-Volmer plots are
Direct evidence on the mechanism of the oxidation of 2, 3-dimethylindole by inorganic peroxo anions.
Balon M, et al.
The Journal of Organic Chemistry, 58(26), 7469-7473 (1993)
Formation of the Ions of Methylindoles in APCI Mass Spectrometry.
Liu DQ and Sun M.
ISRN Spectroscopy, 2012 (2012)
Resolution of heterogeneous fluorescence from proteins and aromatic amino acids by phase-sensitive detection of fluorescence.
J R Lakowicz et al.
The Journal of biological chemistry, 256(12), 6348-6353 (1981-06-25)
Zhengyin Yan et al.
Analytical chemistry, 80(16), 6410-6422 (2008-07-23)
Constant neutral loss (CNL) and precursor ion (PI) scan have been widely used for the in vitro screening of glutathione conjugates derived from reactive metabolites, but these two methods are only applicable to triple quadrupole or hybrid triple quadrupole mass

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