| Identification | More | [Name]
5-(Trifluoromethyl)indole | [CAS]
100846-24-0 | [Synonyms]
5-(TRIFLUOROMETHYL)INDOLE
1H-INDOLE, 5-(TRIFLU OROMETHYL)-(9CI)
5-TRIFLUOROMETHYL INDOLE ,98% | [Molecular Formula]
C9H6F3N | [MDL Number]
MFCD03095341 | [Molecular Weight]
185.15 | [MOL File]
100846-24-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
67-70 °C | [Boiling point ]
256.7±35.0 °C(Predicted) | [density ]
1.367±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder | [pka]
15.94±0.30(Predicted) | [color ]
Yellow | [Sensitive ]
Light Sensitive | [InChIKey]
LCFDJWUYKUPBJM-UHFFFAOYSA-N | [CAS DataBase Reference]
100846-24-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T | [Risk Statements ]
R25:Toxic if swallowed.
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 .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [Uses]
In 3-Naphthylindole construction by rhodium (II)-catalyzed regioselective direct arylation of indoles with 1-diazonaphthalen-2-(1H)-ones treatment of 5-(trifluoromethyl)indole(1k) or 6-(trifluoromethyl)indole (1l) with 2a afforded the desired products 3k (86%)and 3l (86%). | [Synthesis]
Step 5 Synthesis of 5-(trifluoromethyl)indole
To a 250 mL three-necked round-bottomed flask was added N-[2-(3,3-dimethyl-3-silyl-1-ynyl)-4-(trifluoromethyl)phenyl]ethoxycarboxamide (31.5 g, 0.1 mol), EtONa (32.5 g, 0.48 mol) and anhydrous ethanol (200 mL). The reaction mixture was heated to reflux and kept for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel, using a petroleum ether solution of 25% ethyl acetate as eluent to give 14 g (77% yield) of the target product 5-(trifluoromethyl)indole.
1H NMR (300 MHz, DMSO-d6) δ: 8.36 (s, 1H), 7.96-7.94 (m, 1H), 7.46-7.44 (m, 2H), 7.32-7.30 (m, 1H), 6.66-6.64 (m, 1H). | [References]
[1] Patent: US2010/120741, 2010, A1. Location in patent: Page/Page column 92
[2] Patent: WO2011/112731, 2011, A2. Location in patent: Page/Page column 197-198 |
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