| Identification | More | [Name]
5-Chloro-2,3,3-trimethyl-3H-indole | [CAS]
25981-83-3 | [Synonyms]
2,3,3-TRIMETHYL-5-CHLORO-3H-INDOLE
2,3,3-TRIMETHYL-5-CHLORO-INDOLENINE
5-CHLORO-1,3,3-TRIMETHYL-2-METHYLENEINDOLINE
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
5-CHLORO-2,3-DIHYDRO-1,3,3-TRIMETHYL-2-METHYLENE-1H-INDOLE
5-CHLORO-2-METHYLENE-1,3,3-TRIMETHYLINDOLINE
AURORA KA-3417
5-chloro-2,3,3-trimethyl-3h-indol
5-CHLORO-2,3,3-TRIMETHYL-3H-INDOLENINE
5-CHLORO-1,3,3-TRIMETHYL-3H-INDOLE
5-Chloro-2-methylene-2.3.3-Trimethylindoline | [EINECS(EC#)]
247-387-4 | [Molecular Formula]
C11H12ClN | [MDL Number]
MFCD00005814 | [Molecular Weight]
193.67 | [MOL File]
25981-83-3.mol |
| Chemical Properties | Back Directory | [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. ]
Keep in dark place,Inert atmosphere,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]
25981-83-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [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] Dyes and Pigments, 2015, vol. 113, p. 27 - 37
[3] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 2, p. 263 - 269
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1692 - 1696
[5] Patent: WO2004/39894, 2004, A2. Location in patent: Page 37 |
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