| Identification | More | [Name]
5-Nitroindoline | [CAS]
32692-19-6 | [Synonyms]
2,3-DIHYDRO-5-NITRO-(1H)-INDOLE
2,3-DIHYDRO-5-NITROINDOLE
5-NITRO-2,3-DIHYDRO-1H-INDOLE
5-NITROINDOLINE
AKOS BC-0893
2,3-dihydro-5-nitro-1h-indol
5-nitro-indolin | [EINECS(EC#)]
251-158-4 | [Molecular Formula]
C8H8N2O2 | [MDL Number]
MFCD00005709 | [Molecular Weight]
164.16 | [MOL File]
32692-19-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
92-94 °C(lit.) | [Boiling point ]
324.4±31.0 °C(Predicted) | [density ]
1.298±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder | [pka]
0.86±0.20(Predicted) | [color ]
Brown | [InChIKey]
WJQWYAJTPPYORB-UHFFFAOYSA-N | [CAS DataBase Reference]
32692-19-6(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
| [RTECS ]
NM1930000
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [Uses]
5-Nitroindoline was used to prepare acetylated glucosylamines using the Suvorov procedure. | [Synthesis]
General procedure for the synthesis of 5-nitrodihydroindole from 1-(5-nitroindolin-1-yl)ethanone: To a stirred solution of 5-nitroN-acetyldihydroindole (5 g, 31 mmol) in ethanol (50 ml) was slowly added 30% HCl aqueous solution (10 ml) at 50 °C. The reaction mixture was heated to reflux and maintained for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently removed by evaporation under reduced pressure. The resulting residue was alkalized by adjusting to pH 9 with ammonium hydroxide solution and the solid was collected by filtration and dried to give the target product 5-nitrodihydroindole as a yellow solid (3.8 g, 97.43% yield). Mass spectrometry analysis showed MS = m/z 164 [M + 1]. | [References]
[1] Patent: WO2009/109999, 2009, A1. Location in patent: Page/Page column 80
[2] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371
[3] Journal of Organic Chemistry, 1955, vol. 20, p. 1538,1541
[4] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2541,2550; engl. Ausg. S. 2504, 2511
[5] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 817 - 827 |
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