| Identification | Back Directory | [Name]
2,3,3-Trimethyl-5-methoxy-3H-indole | [CAS]
31241-19-7 | [Synonyms]
2,3,3-Trimethyl-5-methoxyindole
5-methoxy-2,3,3-trimethylindole
5-METHOXY-2,3,3-TRIMETHYL-3H-INDOLE
2,3,3-TRIMETHYL-5-METHOXY-3H-INDOLE
2,3,3-Trimethyl 5-Methoxy Indolenine
3H-Indole,5-Methoxy-2,3,3-triMethyl-
2,3,3-TRIMETHYL-5-METHOXY-3H-INDOLE,98+% | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C12H15NO | [MDL Number]
MFCD04972105 | [MOL File]
31241-19-7.mol | [Molecular Weight]
189.25 |
| Chemical Properties | Back Directory | [Boiling point ]
286.7±40.0 °C(Predicted) | [density ]
1.04±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Store in freezer, under -20°C | [pka]
6.60±0.40(Predicted) | [Appearance]
Light yellow to brown Solid |
| Hazard Information | Back Directory | [Uses]
2,3,3-Trimethyl-5-methoxy-3H-indole is used as a key intermediate in the synthesis of the spirane copper ion sensor SP1 [1]. | [Synthesis]
2,3,3-Trimethyl-5-methoxy-3H-indole was prepared by refluxing 4-methoxyphenylhydrazine hydrochloride with 3-methylbutan-2-one in a solution of glacial acetic acid for 5.5 hours. The specific reaction steps are as follows: 4-methoxyphenylhydrazine hydrochloride
(4.815 g, 27.57 mmol) was added to a solution containing 3-methylbutan-2-one (5.90 mL, 55.2 mmol) in glacial acetic acid
(88 mL). The solution was stirred at reflux for 5.5 h. The
solution was allowed to cool to room temperature and
neutralized with KOH pellets. The crude material was
extracted with Et2O (3 × 100 mL), dried over MgSO4,
filtered, and concentrated in vacuo. The crude product was
purified by flash column chromatography (70:30, hexanes/
EtOAc) to afford 2,3,3-trimethyl-5-methoxy-3H-indole as a red
amorphous solid (5.149 g, 99%) [1]. | [References]
[1] Trevino, K. M., Tautges, B. K., Kapre, R. (2021). Highly Sensitive and Selective Spiropyran-Based Sensor for Copper(II) Quantification. ACS Omega, 6 16, 10776–10789. https://doi.org/10.1021/acsomega.1c00392 |
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