4-Aminoindole

Base Information

• Chemical Name: 4-Aminoindole
• CAS No.: 5192-23-4
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 29339990
• Mol file: 5192-23-4.mol

Synonyms:1H-indol-4-amine;

Chemical Property of 4-Aminoindole

Chemical Property:

• Appearance/Colour: greenish-grey to tan powder
• Vapor Pressure: 3.46E-05mmHg at 25°C
• Melting Point: 106-109 °C(lit.)
• Refractive Index: 1.757
• Boiling Point: 354 °C at 760 mmHg
• PKA: 18.23±0.30(Predicted)
• Flash Point: 195 °C
• PSA: 41.81000
• Density: 1.268 g/cm³
• LogP: 2.33130
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble

Purity/Quality:

99% ^*data from raw suppliers

4-Aminoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant 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 4-Aminoindole may be used to synthesize:macrolactam tumour promoter indolactam Vtricyclic structure of 2-substituted-pyrrolo[2,3-h]quinolin-4-one4-azidoindole

Technology Process of 4-Aminoindole

There total 2 articles about 4-Aminoindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1,5,6,7-tetrahydro-indol-4-one (13754-86-4) → 1H-indol-4-ol (2380-94-1) + 4-amino-1H-indole (5192-23-4)

Guidance literature:

With ethene; 5%-palladium/activated carbon; ammonium acetate; In acetonitrile; at 90 ℃; for 15h; under 760.051 Torr; Reagent/catalyst; Schlenk technique;

DOI:10.1021/acs.orglett.0c04056

Reference yield: 41.8%

3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene (78283-21-3,79476-53-2) → 4-amino-1H-indole (5192-23-4) + 4-nitro-1H-indoIe (4769-97-5) + 4-nitro-1-hydroxyindole (78283-23-5) + 1-hydroxy-4-nitrooxyindole (78283-24-6)

Guidance literature:

With titanium(III) chloride; In water; acetic acid; for 0.116667h; Ambient temperature;

DOI:10.1248/cpb.29.726

Reference yield: 79.8%

4-amino-1H-indole (5192-23-4) + 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (189306-94-3) → 5-acetyl-2-ethyl-4-(1H-indol-4-ylamino)-6-phenylpyridazin-3(2H)-one (720716-27-8)

Guidance literature:

In ethanol; at 20 ℃; for 1h;

upstream raw materials:

3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

1,5,6,7-tetrahydro-indol-4-one

Downstream raw materials:

N-benzyl-1H-indol-4-amine

1H-indol-4-ol

4-nitro-1H-indoIe

5-hydroxy-4-nitroindole

Refernces

• 1、 Somei,Inoue,Tokutake,et al.. "The chemistry of indoles. XIII. Syntheses of substituted indoles carrying an amino, nitro, methoxycarbonyl, or benzyloxy group at the 4-position and their 1-hydroxy derivatives". . p. 726 - 738. Retrieved 2007/10/02.