5-Aminoindole Chemical Properties

Melting point:

131-133 °C (dec.) (lit.)

Boiling point:

190 °C / 6mmHg

Density 

1.1083 (rough estimate)

refractive index 

1.6013 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

pka

17.39±0.30(Predicted)

form 

Crystalline Powder

color 

Off-white to gray-brown

Water Solubility 

insoluble

Sensitive 

Air & Light Sensitive

BRN 

112348

InChIKey

ZCBIFHNDZBSCEP-UHFFFAOYSA-N

CAS DataBase Reference

5192-03-0(CAS DataBase Reference)

NIST Chemistry Reference

5-Aminoindole(5192-03-0)

EPA Substance Registry System

5-Aminoindole (5192-03-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-68

Safety Statements 

26-45-36/37

WGK Germany 

3

F 

10

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD

HS Code 

29339990

MSDS

• Language:English Provider:5-Aminoindole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Aminoindole Usage And Synthesis

Chemical Properties

Grey Crystals

Uses

Reactant for preparation of:

• Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP
• Cytotoxic and antimitotic agents
• Insulin-like growth factor 1 receptor inhibitors
• Antitumoral agents
• Factor Xa inhibitor
• Potential antivascular agents
• Gli1-mediated transcription in the Hedgehog pathway
• Inhibitors of receptor tyrosine kinase with antiangiogenic effects
• PKCθ inhibitors
• HIV protease inhibitors

Uses

5-Aminoindole functions as a ligand for hydrophobic charge induction chromatography. A reagent for synthetic elaboration.

Definition

ChEBI: An indolamine carrying an amino group at position 5.

Synthesis

In Example 1, 5-nitroindole was substituted for m-nitroacetophenone as a raw material, maintaining a molar ratio of 1:1. The reaction was carried out at 80 °C for 24 h under hydrogen pressure of 4.0 MPa. Other conditions were consistent with Example 1, and 5-aminoindole was finally obtained in 98% yield. This was done as follows: 16.44 mg (0.04 mmol) of silver 4,4'-dimethoxy-2,2'-bipyridine, 11.22 mg (0.1 mmol) of potassium tert-butanolate and 1 ml of 1,4-dioxane solution were added to an autoclave. After thorough stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred and reacted at 80 °C for 8 hours. Upon completion of the reaction, the reaction solution was extracted with deionized water and dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous Na2SO4 and then subjected to filtration, rotary evaporation and chromatographic separation to afford 3-acetanilide as a yellow solid in 96% yield.

References

[1] Synthetic Communications, 2012, vol. 42, # 2, p. 213 - 222
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1415 - 1422
[3] Organic Letters, 2014, vol. 16, # 1, p. 98 - 101
[4] ACS Catalysis, 2015, vol. 5, # 6, p. 3457 - 3462
[5] Patent: CN106748834, 2017, A. Location in patent: Paragraph 0016; 0029; 0032

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