| Identification | More | [Name]
5-Aminoindole | [CAS]
5192-03-0 | [Synonyms]
1H-INDOL-5-AMINE
1H-INDOL-5-YLAMINE
5-AMINO-1H-INDOLE
5-AMINOINDOLE
5-INDOLAMINE
5-INDOLYLAMINE
AKOS 91148
INDOLE-5-AMINE
TIMTEC-BB SBB004219
Indole, 5-amino-
indol-5-ylamine
5-Aminoindole
H-Indol-5-amine
H-Indol-5-amine
indolin-5-amine
5-AMINOINDOLE 98+%
1H-Indole-5-amine | [EINECS(EC#)]
225-977-2 | [Molecular Formula]
C8H8N2 | [MDL Number]
MFCD00005679 | [Molecular Weight]
132.16 | [MOL File]
5192-03-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Grey Crystals | [Melting point ]
131-133 °C (dec.) (lit.) | [Boiling point ]
190 °C / 6mmHg | [density ]
1.1083 (rough estimate) | [refractive index ]
1.6013 (estimate) | [storage temp. ]
0-6°C | [solubility ]
DMSO, Methanol | [form ]
Crystalline Powder | [pka]
17.39±0.30(Predicted) | [color ]
Off-white to gray-brown | [Water Solubility ]
insoluble | [Sensitive ]
Air & Light Sensitive | [Detection Methods]
HPLC | [BRN ]
112348 | [InChIKey]
ZCBIFHNDZBSCEP-UHFFFAOYSA-N | [CAS DataBase Reference]
5192-03-0(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Aminoindole(5192-03-0) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
5192-03-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R68:Possible risk of irreversible effects. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Grey Crystals | [Uses]
Reactant for preparation of:
- Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP
- Cytotoxic and antimitotic agents
- Insulin-like growth factor 1 receptor inhibitors
- Antitumoral agents
- Factor Xa inhibitor
- Potential antivascular agents
- Gli1-mediated transcription in the Hedgehog pathway
- Inhibitors of receptor tyrosine kinase with antiangiogenic effects
- PKCθ inhibitors
- HIV protease inhibitors
| [Definition]
ChEBI: An indolamine carrying an amino group at position 5. | [Synthesis]
In Example 1, 5-nitroindole was substituted for m-nitroacetophenone as a raw material, maintaining a molar ratio of 1:1. The reaction was carried out at 80 °C for 24 h under hydrogen pressure of 4.0 MPa. Other conditions were consistent with Example 1, and 5-aminoindole was finally obtained in 98% yield. This was done as follows: 16.44 mg (0.04 mmol) of silver 4,4'-dimethoxy-2,2'-bipyridine, 11.22 mg (0.1 mmol) of potassium tert-butanolate and 1 ml of 1,4-dioxane solution were added to an autoclave. After thorough stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred and reacted at 80 °C for 8 hours. Upon completion of the reaction, the reaction solution was extracted with deionized water and dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous Na2SO4 and then subjected to filtration, rotary evaporation and chromatographic separation to afford 3-acetanilide as a yellow solid in 96% yield. | [References]
[1] Synthetic Communications, 2012, vol. 42, # 2, p. 213 - 222
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1415 - 1422
[3] Organic Letters, 2014, vol. 16, # 1, p. 98 - 101
[4] ACS Catalysis, 2015, vol. 5, # 6, p. 3457 - 3462
[5] Patent: CN106748834, 2017, A. Location in patent: Paragraph 0016; 0029; 0032 |
|
|