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4-Aminoindole

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CAS:5192-23-4
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  • 2019-07-06
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4-Aminoindole Basic information
Product Name:4-Aminoindole
Synonyms:4-Aminoindole ,97%;4-Aminoindole;4-AMinoindole, 97% 500MG;(Indol-4-yl)amine;4-Aminoindole in stock Factory;5-methoxyl indole-carboxaldehyde;4-AMINOINDOLINE / 4-INDOLAMINE;4-AMinoindole 97%
CAS:5192-23-4
MF:C8H8N2
MW:132.16
EINECS:621-202-0
Product Categories:Pyrroles & Indoles;Indoles and derivatives;Amines;Pyrroles & Indoles;Indole;Indoles;Building Blocks;Heterocycle-Indole series;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks
Mol File:5192-23-4.mol
4-Aminoindole Structure
4-Aminoindole Chemical Properties
Melting point 106-109 °C (lit.)
Boiling point 354.0±15.0 °C(Predicted)
density 1.268±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form powder to crystal
pka18.23±0.30(Predicted)
color White to Gray to Brown
Water Solubility Insoluble
Sensitive Air Sensitive
BRN 114919
InChIInChI=1S/C8H8N2/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,9H2
InChIKeyLUNUNJFSHKSXGQ-UHFFFAOYSA-N
SMILESN1C2=C(C(N)=CC=C2)C=C1
CAS DataBase Reference5192-23-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-24/25
WGK Germany 3
8-10-34
HazardClass AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD
HS Code 29339990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
4-Aminoindole English
SigmaAldrich English
ACROS English
ALFA English
4-Aminoindole Usage And Synthesis
Chemical PropertiesGreenish-grey to tan powder
UsesReactant for preparation of:• ;Inhibitors of bacterial thymidylate synthase1• ;Mimetics of non-alkaloid toxin lignan anticancer and antiviral agent Podophyllotoxin (PPT)2• ;Inhibitors of Gli1-mediated transcription in the Hedgehog pathway3• ;Protein kinase C θ (PKCθ) inhibitors4• ;Indolic non-peptidic HIV protease inhibitors5• ;Transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonists6• ;Cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors7• ;11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) inhibi
Uses4-Aminoindole may be used to synthesize:
  • macrolactam tumour promoter indolactam V
  • tricyclic structure of 2-substituted-pyrrolo[2,3-h]quinolin-4-one
  • 4-azidoindole
DefinitionChEBI: 4-Aminoindole is a member of indoles.
Synthesis Reference(s)The Journal of Organic Chemistry, 48, p. 5130, 1983 DOI: 10.1021/jo00173a071
General Description4-Aminoindole is an indole derivative. Its cytokinin activity has been assessed by tobacco pith callus bioassay. 4-Aminoindole can be prepared by reacting 2,6-dinitrotoluene and N,N-dimethylformamide dimethylacetal in anhydrous DMF.
Synthesis
4-Nitroindole

4769-97-5

Iron

7439-89-6

4-Aminoindole

5192-23-4

A. Synthesis of 4-aminoindole. Iron powder (1.20 g, 21.58 mmol) and acetic acid (2.47 mL, 43.19 mmol) were sequentially added to a solution of ethanol (20 mL) containing 4-nitroindole (1.0 g, 6.17 mmol). The reaction mixture was heated to reflux for 14 hours. After completion of the reaction, the ethanol solvent was removed by rotary evaporator. The residue was dispersed in a solvent mixture of water and ethyl acetate for extraction and separation. The ethyl acetate layer was collected and dried with anhydrous magnesium sulfate followed by filtration to remove the desiccant. The filtrate was concentrated by rotary evaporation to give the crude product. The crude product was further purified by silica gel column chromatography using 1% methanol/dichloromethane mixture as eluent. The elution fractions containing the target product were collected, combined and the solvent was removed by rotary evaporation to give 0.815 g of 4-aminoindole as an orange solid in 82% yield.

References[1] Patent: US6162818, 2000, A
4-Aminoindole Preparation Products And Raw materials
Raw materials4-Nitroindole-->Iron-->Methanol-->Acetic acid-->Ethanol
Preparation ProductsTosyl-1H-indol-4-amine-->(1H-INDOL-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->4-(Piperazino)indole
Tag:4-Aminoindole(5192-23-4) Related Product Information
4-Nitroindole (-)-INDOLACTAM V 4-(Piperazino)indole 4-Aminoindole 1H-Indol-2-amine 5-BOC-AMINOINDAZOLE METHYL 6-AMINO-4-INDOLECARBOXYLATE 4-Methyl-5-aminoindole 7-Aminoindole 1-BOC-4-AMINOINDOLE (1H-INDOL-5-YL)-CARBAMIC ACID TERT-BUTYL ESTER 5-AMINO-1-N-METHYLINDOLE 7-Aminooxindole 1-(4-Aminoindoline)ethanone ,98% 7-N-BOC-AMINO-INDOLE DL-Tryptophan 1-Boc-5-aminoindole 6-Aminoindole