| Identification | More | [Name]
6-Aminoindole | [CAS]
5318-27-4 | [Synonyms]
1H-INDOL-6-AMINE
6-AMINO-1H-INDOLE
6-AMINOINDOLE
6-Indolamine
INDOLE-6-AMINE
indolin-6-amine
6-AMINOINDOLINE
6-AMINO-BENZOXAZOLE
2,3-Dihydro-1H-indol-6-amine | [EINECS(EC#)]
627-713-5 | [Molecular Formula]
C8H8N2 | [MDL Number]
MFCD02093959 | [Molecular Weight]
132.16 | [MOL File]
5318-27-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
75-79 °C | [Boiling point ]
161-166°C 2mm | [density ]
1.268±0.06 g/cm3(Predicted) | [Fp ]
161-166°C/2mm | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
18.23±0.30(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT-HARMFUL, KEEP COLD | [PackingGroup ]
III | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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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