5-Nitroindoline Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

NM1930000

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Nitroindoline Usage And Synthesis

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

5-Nitroindoline(32692-19-6)Related Product Information

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