5-IODOINDOLE Chemical Properties

Melting point:

101-104 °C (lit.)

Boiling point:

341.7±15.0 °C(Predicted)

Density 

1.960±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

16.14±0.30(Predicted)

form 

Solid or Crystalline Solid

color 

White to pale brown

Sensitive 

Light Sensitive

InChI

InChI=1S/C8H6IN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

InChIKey

TVQLYTUWUQMGMP-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(I)C=C2)C=C1

CAS DataBase Reference

16066-91-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

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

5-IODOINDOLE Usage And Synthesis

Uses

5-Iodoindole is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. It is used as the starting material in the synthesis of 5-(α-fluorovinyl)-N-tosylindole.

General Description

5-Iodoindole can be synthesized via nitration of m-toluidine.

Synthesis

The general procedure for the synthesis of 5-iodoindole from 5-bromoindole was as follows: CuI (9.6 mg, 0.0504 mmol, 5.0 mol%), 5-bromoindole (1.00 mmol if solid), and NaI (300 mg, 2.00 mmol) were added to a Schlenk tube, briefly evacuated and replaced three times with argon. Subsequently, N,N'-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol%), 5-bromoindole (1.00 mmol if liquid) and dioxane (1.0 mL) were added under argon protection. The Schlenk tube was sealed with a polytetrafluoroethylene valve and the reaction mixture was stirred in an oil bath at 110°C for 22-23 hours. Upon completion of the reaction, the suspension was cooled to room temperature, diluted with 30% ammonia solution (5 mL), poured into water (20 mL) and extracted with dichloromethane (3 x 15 mL). The organic phases were combined, dried with anhydrous MgSO? or Na?SO? and concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography to afford the target compound 5-iodoindole.

References

[1] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14844 - 14845
[2] Patent: WO2004/13094, 2004, A2. Location in patent: Page 42-43
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266
[4] Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4
[5] Catalysis Today, 2016, vol. 274, p. 129 - 132

5-IODOINDOLE(16066-91-4)Related Product Information

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