C-(1H-INDOL-5-YL)-METHYLAMINE Chemical Properties

Melting point:

114-122 °C

Boiling point:

335.6±17.0 °C(Predicted)

Density 

1.199±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

17.07±0.30(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C9H10N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H,6,10H2

InChIKey

UAYYSAPJTRVEQA-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(CN)C=C2)C=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

NL4461500

MSDS

• Language:English Provider:SigmaAldrich

C-(1H-INDOL-5-YL)-METHYLAMINE Usage And Synthesis

Uses

5-(Aminomethyl)indole is used in the synthesis of Vigabatrin (V253000) bioisosteres as inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT) inhibitors.

Uses

Reactant for preparation of:

• HIV-1 integrase inhibitors targeting the catalytic domain and its ability for interaction with LEDGF/p75
• Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
• SCIO-469-like compounds for the inhibition of p38 MAP kinase
• 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase c theta (PKC θ) inhibitors
• Non-covalent thrombin inhibitors

Uses

5-(AMinoMethyl)indole has been used as reactant for preparation of:• and HIV-1 integrase inhibitors targeting the catalytic domain and its ability for interaction with LEDGF/p751•

Synthesis

The hydrogenation reaction was carried out using Raney Nickel as a catalyst in a methanol solution containing ammonia with 5-cyanoindole as starting material. After completion of the reaction, the reaction solution was concentrated under reduced pressure to give a light yellow solid product, C-(1H-indol-5-yl)-methylamine (5.25 g, quantitative yield).

References

[1] Patent: US2004/204455, 2004, A1. Location in patent: Page/Page column 18
[2] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4991 - 5002
[3] Patent: US2003/153596, 2003, A1
[4] Patent: WO2016/44770, 2016, A1. Location in patent: Page/Page column 584; 585
[5] Patent: WO2011/76784, 2011, A2. Location in patent: Page/Page column 66

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