6-Aminoindole

Base Information

• Chemical Name: 6-Aminoindole
• CAS No.: 5318-27-4
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 29339900
• European Community (EC) Number: 627-713-5
• NSC Number: 82379
• DSSTox Substance ID: DTXSID30292416
• Nikkaji Number: J80.996I
• Wikidata: Q72438294
• Mol file: 5318-27-4.mol

Synonyms:6-Aminoindole;1H-indol-6-amine;5318-27-4;6-Amino-1H-indole;MFCD02093959;1H-lndol-6-ylamine;6-amino indole;Indol-6-ylamine;indol-6-amine;NSC82379;1H-indol-6-ylamine;6-Aminoindole, 97%;SCHEMBL94619;DTXSID30292416;CL3506;NSC-82379;STK787118;AKOS005206920;AC-3196;AM85804;CS-W001584;DS-1613;PS-4602;SB14954;SY005013;FT-0601476;EN300-52439;A-5680;Z752239752

Chemical Property of 6-Aminoindole

Chemical Property:

• Vapor Pressure: 6.48E-08mmHg at 25°C
• Melting Point: 75-79 °C
• Refractive Index: 1.615
• 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.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: soluble in Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 132.068748264
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

98% ^*data from raw suppliers

6-Aminoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CN2)N
• Uses: Reactant for preparation of:Inhibitors of mammalian target of rapamycin (mTOR ) proteinInhibitors of the AcrAB-TolC efflux pumpInhibitors of Gli1-mediated transcription in the Hedgehog pathwayPotent DNA-topoisomerase II poisons and anti-MDR agentsProtein kinase C θ (PKCθ) inhibitorsPiperidine carboxamide as transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonistsPotent and selective blockers of the Nav1.8 sodium channel as potential analgesics for the treatment of neuropathic and inflammatory pain5,6-fused heteroaromatic ureas as TRPV1 antagonistsAllosteric enhancers of the A3 adenosine receptorHuman liver glycogen phosphorylase (HLGP) inhibitors for the treatment of type 2 diabetes

Technology Process of 6-Aminoindole

There total 12 articles about 6-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: 100.0%

6-nitroindole (4769-96-4) → 6-amino-1H-indole (5318-27-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; under 2587.7 Torr;

DOI:10.1021/jm00171a018

Reference yield: 87.0%

5-bromo-6-nitro-1H-indole (104447-74-7) → 6-amino-1H-indole (5318-27-4)

Guidance literature:

With palladium 10% on activated carbon; hydrazine hydrate; In methanol; at 120 ℃; for 0.25h; Microwave irradiation;

DOI:10.1055/s-0033-1339025

Reference yield: 64.0%

(E)-2-(2,4-dinitrophenyl)-N,N-dimethyl-1-ethenamine (61293-29-6) → 6-amino-1H-indole (5318-27-4)

Guidance literature:

With aluminium amalgam; In water; for 5h; Irradiation;

upstream raw materials:

6-nitroindole

6-bromo-indole-2-carboxylic acid(Ref_.7.)

(E)-2-(2,4-dinitrophenyl)-N,N-dimethyl-1-ethenamine

2,4-dinitrotoluene

Downstream raw materials:

N-(1H-indol-6-yl)acetamide

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(1H-indol-6-ylamino)-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(1H-indol-6-ylamino)-tetrahydro-pyran-3-yl ester

6-bromo-1H-indole

Refernces

• 1、 Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming. "Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications". supporting information. p. 1618 - 1629. Retrieved 2021/01/25.
• 2、 Bento, Ian,Bernaldez, Mabel,Noguchi, Ryden,Kawakami, Joel. "Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal". supporting information. p. 1404 - 1407. Retrieved 2020/03/31.