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120812

Sigma-Aldrich

2,3-Dimethylindole

≥97%

Synonym(s):

NSC 24936

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About This Item

Empirical Formula (Hill Notation):
C10H11N
CAS Number:
91-55-4
Molecular Weight:
145.20
EC Number:
202-076-2
MDL number:
MFCD00005617
UNSPSC Code:
12352100
PubChem Substance ID:
24847431
NACRES:
NA.22

Assay

≥97%

form

solid

bp

285 °C (lit.)

mp

105-107 °C (lit.)

SMILES string

Cc1[nH]c2ccccc2c1C

InChI

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

InChI key

PYFVEIDRTLBMHG-UHFFFAOYSA-N

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

120812-25G:
120812-BULK:
120812-VAR:
120812-500G:
120812-5G:

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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Sigma-Aldrich

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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)
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
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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