5-Aminoindole

Base Information

• Chemical Name: 5-Aminoindole
• CAS No.: 5192-03-0
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 29339990
• European Community (EC) Number: 225-977-2
• NSC Number: 61452
• UNII: Q732PG0Y16
• DSSTox Substance ID: DTXSID5063734
• Nikkaji Number: J80.971C
• Wikidata: Q27115500
• Metabolomics Workbench ID: 54801
• ChEMBL ID: CHEMBL325916
• Mol file: 5192-03-0.mol

Synonyms:1-aminoindole;5-aminoindole;7-aminoindole

Chemical Property of 5-Aminoindole

Chemical Property:

• Appearance/Colour: Grey Crystals
• Vapor Pressure: 3.46E-05mmHg at 25°C
• Melting Point: 131-133 °C (dec.)(lit.)
• Refractive Index: 1.757
• Boiling Point: 354 °C at 760 mmHg
• PKA: 17.39±0.30(Predicted)
• Flash Point: 195 °C
• PSA: 41.81000
• Density: 1.268 g/cm³
• LogP: 2.33130
• Storage Temp.: 0-6°C
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO, Methanol
• Water Solubility.: insoluble
• XLogP3: 0.7
• 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:

99% ^*data from raw suppliers

5-Aminoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-68
• Safety Statements: 26-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1N
• Uses: Reactant for preparation of:Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAPCytotoxic and antimitotic agentsInsulin-like growth factor 1 receptor inhibitorsAntitumoral agentsFactor Xa inhibitorPotential antivascular agentsGli1-mediated transcription in the Hedgehog pathwayInhibitors of receptor tyrosine kinase with antiangiogenic effectsPKCθ inhibitorsHIV protease inhibitors 5-Aminoindole functions as a ligand for hydrophobic charge induction chromatography. A reagent for synthetic elaboration.

Technology Process of 5-Aminoindole

There total 22 articles about 5-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: 99.0%

5-nitroindole (6146-52-7) → 5-amino-1H-indole (5192-03-0)

Guidance literature:

With hydrazine hydrate; at 90 ℃; for 1.5h; chemoselective reaction;

DOI:10.1080/00397911.2010.523159

Reference yield: 90.0%

indol-5-ol (1953-54-4) → 5-amino-1H-indole (5192-03-0)

Guidance literature:

With sodium tetrahydroborate; 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide; In 1,4-dioxane; at 170 ℃; for 16h; Molecular sieve; Inert atmosphere;

DOI:10.1039/c9sc00595a

Reference yield: 85.0%

5-nitro-2,3-dihydro-1H-indole (32692-19-6) → 5-amino-1H-indole (5192-03-0)

Guidance literature:

With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide; In tert-Amyl alcohol; at 95 ℃; for 48h;

DOI:10.1021/acs.orglett.0c02271

upstream raw materials:

5-nitroindole

1-(5-nitro-2,3-dihydroindol-1-yl)ethanone

7-bromo-5-nitro-1H-indole

5-phenylazoindole

Downstream raw materials:

N-(1H-indol-5-yl)benzamide

(1H-Indol-5-yl)-(1-phenethyl-piperidin-4-ylidene)-amine

9-(5-indolyl)aminoacridine

C₂₃H₂₃N₅O₅

Refernces

• 1、 Taskesenligil, Yunus,Lafzi, Ferruh,Kilic, Haydar,Saracoglu, Nurullah. "Palladium-catalyzed regioselective C2-arylation of 5-aminoindole". . p. 3289 - 3296. Retrieved 2019.
• 2、 Tu, Shun,Zhang, Ting-jian,Zhang, Yi,Zhang, Xu,Zhang, Zhen-hao,Meng, Fan-hao. "N-(3-cyano-1H-indol-5-yl)isonicotinamide and N-(3-cyano-1H-indol-5-yl)-1H-benzo[d]imidazole-5-carboxamide derivatives: Novel amide-based xanthine oxidase inhibitors". . . Retrieved 2021/07/31.
• 3、 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.