5-Aminoindole

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CAS:5192-03-0
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5-Aminoindole Basic information
Product Name:5-Aminoindole
Synonyms:TIMTEC-BB SBB004219;5-AMINO-1H-INDOLE;5-AMINOINDOLE;5-INDOLYLAMINE;5-INDOLAMINE;AKOS 91148;1H-INDOL-5-AMINE;1H-INDOL-5-YLAMINE
CAS:5192-03-0
MF:C8H8N2
MW:132.16
EINECS:225-977-2
Product Categories:Heterocycle-Indole series;Amines;Aromatics;Simple Indoles;Indole Derivatives;IndoleDerivative;Indoles;indole derivative;Indoles and derivatives
Mol File:5192-03-0.mol
5-Aminoindole Structure
5-Aminoindole Chemical Properties
Melting point 131-133 °C (dec.) (lit.)
Boiling point 190 °C / 6mmHg
density 1.1083 (rough estimate)
refractive index 1.6013 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMSO, Methanol
pka17.39±0.30(Predicted)
form Crystalline Powder
color Off-white to gray-brown
Water Solubility insoluble
Sensitive Air & Light Sensitive
BRN 112348
InChI1S/C8H8N2/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,9H2
InChIKeyZCBIFHNDZBSCEP-UHFFFAOYSA-N
SMILESNc1ccc2[nH]ccc2c1
CAS DataBase Reference5192-03-0(CAS DataBase Reference)
NIST Chemistry Reference5-Aminoindole(5192-03-0)
EPA Substance Registry System5-Aminoindole (5192-03-0)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-68
Safety Statements 26-45-36/37
WGK Germany 3
10
Hazard Note Irritant
TSCA TSCA listed
HazardClass AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD
HS Code 29339990
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Dermal
Acute Tox. 4 Oral
Aquatic Acute 1
Eye Irrit. 2
MSDS Information
ProviderLanguage
5-Aminoindole English
SigmaAldrich English
ACROS English
ALFA English
5-Aminoindole Usage And Synthesis
Chemical PropertiesGrey Crystals
UsesReactant 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
Uses5-Aminoindole functions as a ligand for hydrophobic charge induction chromatography. A reagent for synthetic elaboration.
DefinitionChEBI: An indolamine carrying an amino group at position 5.
Synthesis
5-Nitroindole

6146-52-7

5-Aminoindole

5192-03-0

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
5-Aminoindole Preparation Products And Raw materials
Raw materialsEthanol-->Iron-->Polyphosphoric acid-->Quinoline-->Ethyl pyruvate-->Cupric oxide-->4-Nitrophenylhydrazine-->5-Bromoindole-->1-Boc-5-aminoindole-->5-Nitroindole
Preparation Products5-(2,5-DIMETHYLPYRROL-1-YL)-INDOLE
Tag:5-Aminoindole(5192-03-0) Related Product Information
Bis(2-ethylhexyl)amine Indometacin Indole Triallylamine Dibenzylamine Indole-3-acetic acid Indole-3-butyric acid REMASTRAL BLUE FFRL 4-Aminoindole;4-Indolamine 4-(3-CARBAZOLYLAMINO)PHENOL 1-ACETYL-5-NITROINDOLINE 2-METHYL-5-NITROINDOLE 1,3,6,8-TETRANITROCARBAZOLE 5-Nitroindoline 2,3-DIMETHYL-5-NITROINDOLE 5-Nitroindole 9-Ethyl-3-nitrocarbazole 5-Nitroisatin

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