| Identification | Back Directory | [Name]
C-(1H-INDOL-5-YL)-METHYLAMINE | [CAS]
81881-74-5 | [Synonyms]
INDOLE-5-METHYLAMINE
Indole-5-methanamine
5-(AMINOMETHYL)INDOLE
5-(aminomethyl)-indol
1H-Indole-5-MethanaMine
((Indol-5-yl)Methyl)aMine
(1H-Indol-5-yl)methylamine
(1H-INDOL-5-YL)METHANAMINE
1-(1H-Indol-5-yl)MethanaMine
C-(1H-INDOL-5-YL)-METHYLAMINE | [Molecular Formula]
C9H10N2 | [MDL Number]
MFCD01719220 | [MOL File]
81881-74-5.mol | [Molecular Weight]
146.19 |
| Chemical Properties | Back Directory | [Melting point ]
114-118 °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 |
| Hazard Information | Back Directory | [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/p751• ;Inhibitors of Gli1-mediated transcription in the Hedgehog pathway2• ;SCIO-469-like compounds for the inhibition of p38 MAP kinase3• ;4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase c theta (PKC θ) inhibitors4• ;Non-covalent thrombin inhibitors5 | [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 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [RTECS ]
NL4461500 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
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