1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE Chemical Properties

Melting point:

36-40℃

Boiling point:

388℃

Density 

1.56

Flash point:

189℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Light yellow to yellow <36°C Solid,>40°C Liquid

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

InChI

InChI=1S/C13H14INO2/c1-13(2,3)17-12(16)15-8-10(14)9-6-4-5-7-11(9)15/h4-8H,1-3H3

InChIKey

LOFWPZQNSUAMCV-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C2=C(C=CC=C2)C(I)=C1

Safety Information

HS Code 

2933998090

1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE Usage And Synthesis

Uses

1-Boc-3-iodoindole is used as a pharmaceutical intermediate and also used in ceramic manufacturing industry.

Synthesis

In a dry reaction flask, 3-iodo-1H-indole (23.1 g, 95.05 mmol) was dissolved in dichloromethane (200 mL). Subsequently, triethylamine (24 g, 237.6 mmol) and di-tert-butyl dicarbonate (20.75 g, 95.07 mmol) were added sequentially to this solution. The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until the complete disappearance of the ingredients. After completion of the reaction, water was added to the mixture and extracted with ethyl acetate. The organic phases were combined and dried with anhydrous sodium sulfate. Finally, the solvent was removed by rotary evaporator to afford 1-Boc-3-iodoindole (27.7 g, 85% yield).

References

[1] Organic Letters, 2018, vol. 20, # 7, p. 1978 - 1981
[2] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6706 - 6710
[3] Tetrahedron, 2000, vol. 56, # 43, p. 8473 - 8480
[4] Patent: CN104876914, 2017, B. Location in patent: Paragraph 0313-0315
[5] Patent: WO2017/173604, 2017, A1. Location in patent: Page/Page column 19; 20

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