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246255

Sigma-Aldrich

5,6-Dimethoxyindole

99%

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About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
14430-23-0
Molecular Weight:
177.20
Beilstein:
5683
EC Number:
238-402-5
MDL number:
MFCD00005675
UNSPSC Code:
12352100
PubChem Substance ID:
24854798
NACRES:
NA.22

Assay

99%

form

solid

mp

154-157 °C (lit.)

SMILES string

COc1cc2cc[nH]c2cc1OC

InChI

1S/C10H11NO2/c1-12-9-5-7-3-4-11-8(7)6-10(9)13-2/h3-6,11H,1-2H3

InChI key

QODBZRNBPUPLEZ-UHFFFAOYSA-N

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Application

5,6-Dimethoxyindole was used in the synthesis of N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide.
  • Reactant in synthesis of indolylhydroxyoxindoles via enantioselective Friedel-Crafts reaction
  • Reactant in synthesis of benzyl trimethoxyindoles
  • Reactant for synthesis of benzoylpiperazinyl-indolyl ethane dione derivatives as HIV-1 inhibitors
  • Reactant for synthesis of 1-aroylindole 3-aroylindoles combretastatin A-4 analogs as antitumor agents and tubulin polymerization inhibitors
  • Reactant for preparation of tryptophanol derivatives via the Grignard reaction

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

246255-BULK:
246255-VAR:
246255-1G:
246255-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD4055
MKBS0455V
MKBN9129V
MKBL7672V
MKBJ0946V

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J Hirschinger et al.
Solid state nuclear magnetic resonance, 3(3), 121-135 (1994-06-01)
The inversion-recovery cross-polarization (IRCP) magic-angle spinning experiment has been applied to study the 13C-1H cross-polarization dynamics of protonated aromatic carbons in ferrocene, 5,6-dimethoxyindole (DMI) and some indole derivatives. Using the 13C-detected proton spin diffusion (SD) experiment recently developed by Zhang
W B Emary et al.
Rapid communications in mass spectrometry : RCM, 3(12), 413-416 (1989-12-01)
It is not possible to distinguish isomers of biologically important dimethoxyindoles using electron-ionization mass spectra, but they may be distinguished by collisionally activated dissociation. In particular, energy-resolved mass spectrometry yields the best data for distinguishing between these isomers.
F Chimenti et al.
Il Farmaco; edizione scientifica, 35(9), 785-790 (1980-09-01)
The synthesis of two new N-cyclopropyltryptamines is described. By treating 5,6-dimethoxyindole with oxalyl chloride and N-benzylcyclopropylamine, N-benzyl-N-cyclopropyl-5,6-dimethoxyindole-3-glyoxalamide is obtained. The reduction of this compound by LiAlH4, gives N-benzyl-N-cyclopropyl-5,6-dimethoxytryptamine, which is hydrogenated to N-cyclopropyl-5,6-dimethoxytryptamine. Similarly N-cyclopropyl-6,7-dimethoxytryptamine is prepared. Preliminary results indicate

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