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Home > Encyclopedia > 6-Aminoindole

6-Aminoindole

6-Aminoindole structure

6-Aminoindole 

structure
  • CAS No:

    5318-27-4

  • Formula:

    C8H8N2

  • Chemical Name:

    6-Aminoindole

  • Synonyms:

    NSC 82379;6-Indolamine;6-AMINOINDOLE;INDOLE-6-AMINE;6-AMINOINDOLINE;indolin-6-amine;Indol-6-ylamine;1H-INDOL-6-AMINE;6-AMINO-1H-INDOLE;1H-Indol-6-ylaMine

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Solid

6-Aminoindole Basic Attributes

132.16

132.068741

112190

226-176-0

82379

DTXSID30292416

29339900

Characteristics

41.8

1.9

White to brown Crystalline Powder

1.3±0.1 g/cm3

75-79 °C

161-166°C2mm

161-166°C/2mm

1.758

Keep Cold

Safety Information

III

IRRITANT-HARMFUL, KEEP COLD

NONH for all modes of transport

3

22-36/37/38

26-36

Xn,Xi

Harmful

P261-P305 + P351 + P338

H302-H315-H319-H335

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

6-Aminoindole Use and Manufacturing

Methods of Manufacturing

In Example 1, the m-nitroacetophenone used was replaced with an equimolar 6-nitroindole at a hydrogen pressure of4.0 MPa at 80 ° C for 48 hours. The other procedure was the same as in to give 6-aminoindole in a yield of 94percent, _: A solution of 16.44 mg (0.04 mmol) 4, 4'-dimethoxy-2, 2'-bipyridine silver 11.22 mg (0.1 mmol) of potassuim t-butoxide and 1 mL of 1, 4-dioxane were charged into an autoclave. After stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred at 80 °C. The reaction was carried out for 8 hours. After the reaction has finishedm the reaction solution was extracted with water and dichloromethane to collect the organic phase. Then, the organic phase was dried over anhydrous NaGeneral procedure: A mixture of compounds 1–4 (6.13 mmol) in ethanol (30 mL) was treated with 10percent Pd/C (20 wt. percentof 1–4) and subjected overnight to 50 psi HGeneral procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.

Uses

Organic compounds are used to synthesize various compounds in the organic synthesis

Computed Properties

Molecular Weight:132.16
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:41.8
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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