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246255

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24854798
EC Number:
238-402-5
Beilstein/REAXYS Number:
5683
MDL number:
MFCD00005675
Assay:
99%
Form:
solid
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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

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

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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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
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
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.

Global Trade Item Number

SKUGTIN
246255-1G04061825858814