| Identification | More | [Name]
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE | [CAS]
13754-86-4 | [Synonyms]
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
1,5,6,7-TETRAHYDRO-4H-INDOLE-4-ONE
1,5,6,7-TETRAHYDRO-INDOL-4-ONE
4-OXO-4,5,6,7-TETRAHYDROINDOLE
4-Oxo-1,5,6,7-tetrahydroindole
Tetrahydroindolone
4-0xo-4,5,6,7-tetrahydroindole
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE 97+%
4,5,6,7-Tetrahydro-1H-indol-4-one | [Molecular Formula]
C8H9NO | [MDL Number]
MFCD00075438 | [Molecular Weight]
135.16 | [MOL File]
13754-86-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
188-190 °C (lit.) | [Boiling point ]
311℃ | [density ]
1.216 | [Fp ]
150℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
powder to crystal | [pka]
15.91±0.20(Predicted) | [color ]
White to Light yellow to Light orange | [InChI]
InChI=1S/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2 | [InChIKey]
KASJZXHXXNEULX-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(=O)CCC2)C=C1 | [CAS DataBase Reference]
13754-86-4(CAS DataBase Reference) |
| 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 ]
2914390090 |
| Hazard Information | Back Directory | [Uses]
• ;Reactant in synthesis of psammopemmin A as antitumor agent1• ;Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions2• ;Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase3• ;Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles4• ;Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids foll | [General Description]
Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl--4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate) yields α-iodo derivative as the main product. | [Synthesis]
The general procedure for the synthesis of 1,5,6,7-tetrahydro-4H-indol-4-one from 6,7-dihydro-4(5H)-benzofuranone is as follows: 6,7-dihydro-4(5H)-benzofuranone (0.10 g, 0.73 mmol) was dissolved in 20% aqueous ethanol (ca. 2 mL) along with the corresponding amine (3 equiv.) in an airtight tube at 150°C, respectively, and was Heating for 12 h or 36 h, respectively. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) and the resulting aqueous solution was extracted with dichloromethane (3 x 10 mL). The organic extracts were combined, dried with anhydrous magnesium sulfate and concentrated to give a brown residue. This residue was purified by silica gel column chromatography with a solvent mixture of ethyl acetate/petroleum ether as eluent. | [References]
[1] Heterocycles, 1984, vol. 22, # 10, p. 2313 - 2316
[2] Tetrahedron Letters, 2012, vol. 53, # 33, p. 4276 - 4279
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 1, p. 341 - 343 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)MS
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)1HNMR
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)13CNMR
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)IR1
1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)IR2
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