| Identification | More | [Name]
5,6-DIMETHOXYINDOLE | [CAS]
14430-23-0 | [Synonyms]
5,6-DIMETHOXY-1H-INDOLE
5,6-DIMETHOXYINDOLE
AKOS JY2083477
1H-Indole, 5,6-dimethoxy-
5,6-Dimethoxyindole 99% | [EINECS(EC#)]
238-402-5 | [Molecular Formula]
C10H11NO2 | [MDL Number]
MFCD00005675 | [Molecular Weight]
177.2 | [MOL File]
14430-23-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige powder | [Melting point ]
154-157 °C (lit.) | [Boiling point ]
198°C 8mm | [density ]
1.182±0.06 g/cm3(Predicted) | [Fp ]
198°C/8mm | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Powder | [pka]
16.93±0.30(Predicted) | [color ]
Beige | [Water Solubility ]
Insoluble in water. | [λmax]
306nm(EtOH)(lit.) | [BRN ]
5683 | [InChI]
InChI=1S/C10H11NO2/c1-12-9-5-7-3-4-11-8(7)6-10(9)13-2/h3-6,11H,1-2H3 | [InChIKey]
QODBZRNBPUPLEZ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(OC)C(OC)=C2)C=C1 | [CAS DataBase Reference]
14430-23-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Beige powder | [Uses]
An indole derivative as analgesic antiinflammatory | [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 | [Synthesis Reference(s)]
Journal of the American Chemical Society, 75, p. 5887, 1953 DOI: 10.1021/ja01119a030 | [Synthesis]
The general procedure for the synthesis of 5,6-dimethoxyindole from the compound (CAS: 65907-71-3) is as follows (note: use the Biotage Initiator? for microwave reactions in a 2-5 mL reaction vessel): in a microwave reactor vial, an appropriate amount of o-nitrostyrene or o-nitrocinnamate (0.3 mmol) was combined with phosphine (2.4 equiv) A suspension was formed by stirring in anhydrous solvent (5 mL) and oxygen was excluded by bubbling argon into the mixture. The vessel was sealed by adding MoO2Cl2(dmf)2 (5 mol%). The reaction mixture was heated to the indicated temperature under microwave radiation and maintained for the corresponding time. Post-reaction treatments vary depending on the phosphine used: when triphenylphosphine is used, the solvent is removed under vacuum and the product is purified by column chromatography (hexane-EtOAc); when polystyrene-loaded triphenylphosphine is used, the reaction mixture is filtered and the solvent is removed under vacuum to obtain a pure indole; when 2-(diphenylphosphino)benzoic acid is used, the reaction mixture is filtered and washed with alkali if necessary. Post-reaction treatments of other phosphines were carried out with reference to the methods described in the literature [14] [15]. | [References]
[1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1339 - 1342 |
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