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| | 5-Chloro-2,3,3-trimethyl-3H-indole Basic information |
| Product Name: | 5-Chloro-2,3,3-trimethyl-3H-indole | | Synonyms: | AURORA KA-3417;5-CHLORO-1,3,3-TRIMETHYL-2-METHYLENEINDOLINE;5-CHLORO-2,3-DIHYDRO-1,3,3-TRIMETHYL-2-METHYLENE-1H-INDOLE;5-CHLORO-2,3,3-TRIMETHYL-3H-INDOLE;5-CHLORO-2,3,3-TRIMETHYLINDOLE;5-CHLORO-2,3,3-TRIMETHYL-INDOLENINE;5-CHLORO-2,3,3-TRIMETHYLINDOLINE;2,3,3-TRIMETHYL-5-CHLORO-3H-INDOLE | | CAS: | 25981-83-3 | | MF: | C11H12ClN | | MW: | 193.67 | | EINECS: | 247-387-4 | | Product Categories: | Heterocyclic Acids;Heterocycle-Indole series;Halides;Pyrroles & Indoles;Indole;Pyrroles & Indoles | | Mol File: | 25981-83-3.mol |  |
| | 5-Chloro-2,3,3-trimethyl-3H-indole Chemical Properties |
| Boiling point | 271.1±40.0 °C(Predicted) | | density | 1.083 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.594(lit.) | | Fp | >230 °F | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | form | solid | | pka | 4.87±0.40(Predicted) | | color | Red | | InChI | InChI=1S/C11H12ClN/c1-7-11(2,3)9-6-8(12)4-5-10(9)13-7/h4-6H,1-3H3 | | InChIKey | GSKATGIMEUGNJN-UHFFFAOYSA-N | | SMILES | N1C2=C(C=C(Cl)C=C2)C(C)(C)C=1C | | CAS DataBase Reference | 25981-83-3(CAS DataBase Reference) | | EPA Substance Registry System | 3H-Indole, 5-chloro-2,3,3-trimethyl- (25981-83-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 2933998090 |
| | 5-Chloro-2,3,3-trimethyl-3H-indole Usage And Synthesis |
| Synthesis | GENERAL METHOD: 3-methyl-2-butanone (1.2 eq.) and p-chlorophenylhydrazine hydrochloride (1 g) were sequentially added to a 10 mL microwave reaction tube equipped with a magnetic stirrer. Subsequently, deionized water (3 mL) and sulfuric acid (0.1 equiv) were added to the reaction mixture. The reaction tube was sealed and placed in a microwave reactor and radiated at 100 °C for 10 min until the feedstock was completely converted. Upon completion of the reaction, the aqueous layer was removed and saturated sodium bicarbonate solution (3 mL) was added to the residue to neutralize the reaction solution. The mixture was sonicated for 10 min to completely quench the residual acidity. The organic layer was separated and the resulting oily product was dissolved in a minimum volume of dichloromethane and dried by adding anhydrous sodium sulfate for 30 minutes. After gravity filtration, the filtrate was concentrated to obtain 5-chloro-2,3,3-trimethylindole in quantitative yield. | | References | [1] Dyes and Pigments, 2015, vol. 113, p. 27 - 37
[2] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 2, p. 263 - 269
[3] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1692 - 1696
[4] Patent: WO2004/39894, 2004, A2. Location in patent: Page 37 |
| | 5-Chloro-2,3,3-trimethyl-3H-indole Preparation Products And Raw materials |
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