6-Aminoindole Chemical Properties

Melting point:

75-79 °C

Boiling point:

161-166°C 2mm

Density 

1.268±0.06 g/cm3(Predicted)

Flash point:

161-166°C/2mm

storage temp. 

-20°C

solubility 

soluble in Methanol

pka

18.23±0.30(Predicted)

form 

Crystalline Powder

color 

White to brown

Sensitive 

Air Sensitive

BRN 

112190

InChI

InChI=1S/C8H8N2/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H,9H2

InChIKey

MIMYTSWNVBMNRH-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(N)=C2)C=C1

CAS DataBase Reference

5318-27-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT-HARMFUL, KEEP COLD

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:6-Aminoindole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-Aminoindole Usage And Synthesis

Chemical Properties

Solid

Uses

Reactant for preparation of:

• Inhibitors of mammalian target of rapamycin (mTOR ) protein
• Inhibitors of the AcrAB-TolC efflux pump
• Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
• Potent DNA-topoisomerase II poisons and anti-MDR agents
• Protein kinase C θ (PKCθ) inhibitors
• Piperidine carboxamide as transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonists
• Potent and selective blockers of the Nav1.8 sodium channel as potential analgesics for the treatment of neuropathic and inflammatory pain
• 5,6-fused heteroaromatic ureas as TRPV1 antagonists
• Allosteric enhancers of the A3 adenosine receptor
• Human liver glycogen phosphorylase (HLGP) inhibitors for the treatment of type 2 diabetes

Synthesis

In Example 1, 6-nitroindole was used as a raw material and reacted at 4.0 MPa hydrogen pressure and 80°C for 48 hours to carry out a hydrogenation reduction reaction. Other steps were the same as in Example 1, and 6-aminoindole was finally obtained in 94% yield. The specific operation was as follows: 16.44 mg (0.04 mmol) of silver 4,4'-dimethoxy-2,2'-bipyridine and 11.22 mg (0.1 mmol) of potassium tert-butoxide were dissolved in 1 mL of 1,4-dioxane and added to an autoclave. After stirring well, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the reaction was stirred at 80 °C for 8 hours. At the end of the reaction, the reaction solution was extracted with water and dichloromethane to separate the organic phase. The organic phase was dried over anhydrous Na2SO4, and then subjected to filtration, rotary evaporation and chromatographic separation to obtain a yellow solid 3-acetanilide in 96% yield.

References

[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2437 - 2451
[2] Patent: US2005/70534, 2005, A1. Location in patent: Page/Page column 14
[3] Patent: CN106748834, 2017, A. Location in patent: Paragraph 0016; 0033; 0036
[4] Molecules, 2014, vol. 19, # 1, p. 925 - 939
[5] Catalysis Communications, 2016, vol. 84, p. 25 - 29

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