7-Aminoindole Chemical Properties

Melting point:

96-100 °C

Boiling point:

354.0±15.0 °C(Predicted)

Density 

1.268±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

17.68±0.30(Predicted)

color 

Black

Sensitive 

Air Sensitive

BRN 

471787

CAS DataBase Reference

5192-04-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

Hazard Note 

Harmful/Irritant/Keep Cold

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:7-Indolamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

7-Aminoindole Usage And Synthesis

Uses

Reactant for preparation of:• ;Fluorescent anion receptors and sensors1,2• ;Sulfate receptors3• ;Protein Kinase C θ (PKCθ) inhibitors4• ;Factor Xa Inhibitors5• ;Aurora kinase inhibitor• ;Antagonist of Mineralocorticoid Receptor6• ;Potent histone deacetylase (HDAC) inhibitors7• ;TRPV1 antagonists8• ;Derivatives of N-(7-indolyl)benzenesulfonamide as cell cycle inhibitors9

Uses

Reactant for preparation of:

• Fluorescent anion receptors and sensors
• Sulfate receptors
• Protein Kinase C θ (PKCθ) inhibitors
• Factor Xa Inhibitors
• Aurora kinase inhibitor
• Antagonist of Mineralocorticoid Receptor
• Potent histone deacetylase (HDAC) inhibitors
• TRPV1 antagonists
• Derivatives of N-(7-indolyl)benzenesulfonamide as cell cycle inhibitors

Definition

ChEBI: 1H-indol-7-amine is an indolamine.

Synthesis

The general procedure for the synthesis of 7-aminoindoles using 7-nitroindoles as starting material is as follows: 7-nitroindoles were dissolved in ethanol according to the method described in Scheme VII (step A). To this solution was added ammonium formate (10 equivalents) and a catalytic amount of 10% palladium carbon. Subsequently, the reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, it was cooled to room temperature, filtered through a diatomaceous earth pad to remove the catalyst, and the filtrate was concentrated under reduced pressure to give 7-aminoindole in purple solid form in 99% yield.

References

[1] Patent: WO2004/67529, 2004, A1. Location in patent: Page 75 - 76
[2] Patent: WO2005/92854, 2005, A1. Location in patent: Page/Page column 53
[3] Green Chemistry, 2017, vol. 19, # 3, p. 809 - 815
[4] Synthetic Communications, 2018, vol. 48, # 19, p. 2475 - 2484
[5] Patent: WO2005/92854, 2005, A1. Location in patent: Page/Page column 56-57

7-Aminoindole(5192-04-1)Related Product Information

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