1-methyl-1H-indol-5-amine

Base Information

• Chemical Name: 1-methyl-1H-indol-5-amine
• CAS No.: 102308-97-4
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• Hs Code.: 29339900
• European Community (EC) Number: 641-208-7
• DSSTox Substance ID: DTXSID60377760
• Nikkaji Number: J1.991.144F
• Wikidata: Q72439619
• ChEMBL ID: CHEMBL4216063
• Mol file: 102308-97-4.mol

Synonyms:1-methyl-1H-indol-5-amine;102308-97-4;5-Amino-1-N-methylindole;1-methylindol-5-amine;1-Methyl-1H-indol-5-ylamine;1h-indol-5-amine, 1-methyl-;5-amino-1-methyl-1h-indole;MFCD03839873;CHEMBL4216063;1-methyl-5-amino-1h-indole;1-methylindole-5-ylamine;1-methyl-5-aminoindole;5-amino-1-methylindole;5-amino-1-methyl-indole;(1-Methylindol-5-yl)amine;SCHEMBL721707;1-Methyl-1H-indole-5-amine;DTXSID60377760;PGTSGPCXPIFQEL-UHFFFAOYSA-N;HMS1702C02;BDBM50455628;AKOS000505691;5-amino-1-N-Methylindole, AldrichCPR;AC-6688;CS-W021349;PS-5817;SB15029;SY063835;BB 0261976;FT-0630144;EN300-783282;Q-102911;F5608-0075;Z385461802;9TT

Chemical Property of 1-methyl-1H-indol-5-amine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 102 °C
• Refractive Index: 1.62
• Boiling Point: 328.036 °C at 760 mmHg
• PKA: 5.05±0.10(Predicted)
• Flash Point: 152.191 °C
• PSA: 30.95000
• Density: 1.15g/cm³
• LogP: 2.34170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Amino-1-N-methylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-36-22-20/21/22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=CC2=C1C=CC(=C2)N
• Uses: 5-Amino-1-N-methylindole (CAS# 102308-97-4) is an indole derivative and building block, used in the copper-catalyzed synthesis of sulfonamides.

Technology Process of 1-methyl-1H-indol-5-amine

There total 15 articles about 1-methyl-1H-indol-5-amine 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%

1-methyl-5-nitro-1H-indole (29906-67-0) → 1-methyl-1H-indol-5-amine (102308-97-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.ejmech.2018.08.077

Reference yield: 99.0%

→ 1-methyl-1H-indol-5-amine (102308-97-4)

Guidance literature:

With C₃₀H₄₄Cl₃CrN₂O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 60 ℃; for 24h;

Reference yield: 95.0%

5-amino-1H-indole (5192-03-0) + tetramethylammonium fluoride (373-68-2) → 1-methyl-1H-indol-5-amine (102308-97-4)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 160 ℃; for 24h; Solvent; Temperature; chemoselective reaction;

DOI:10.1021/acs.orglett.9b04400

upstream raw materials:

N-(1-methyl-indol-5-yl)-phthalimide

1-methyl-5-nitro-1H-indole

methanol

thiophenol

Downstream raw materials:

N-(1-Methyl-1H-indol-5-yl)-1-(4-isopropylphenyl)-1H-indole-2-carboxamide

C₂₃H₁₈N₄

Refernces

• 1、 Gasparotto, Venusia,Castagliuolo, Ignazio,Ferlin, Maria Grazia. "3-Substituted 7-phenyl-pyrroloquinolinones show potent cytotoxic activity in human cancer cell lines". . p. 5509 - 5513. Retrieved 2007.
• 2、 Schulz, Thomas,Torborg, Christian,Enthaler, Stephan,Schaeffner, Benjamin,Dumrath, Andreas,Spannenberg, Anke,Neumann, Helfried,Boerner, Armin,Beller, Matthias. "A general palladium-catalyzed animation of aryl halides with ammonia". . p. 4528 - 4533. Retrieved 2009.
• 3、 Bouchard, Luc,Marcotte, Ian,Chapuzet, Jean Marc,Lessard, Jean. "Electroreduction of 1-methyl 5-nitroindole, 5-nitrobenzofurane, and 5-nitrobenzothiophene in acidic and basic hydroorganic media: Generation and trapping of iminoquinone-type intermediates and electrosynthesis of ring-substituted amino derivatives". . p. 1108 - 1118. Retrieved 2003.
• 4、 Chen, Shujie,Lu, Guoping,Cai, Chun. "Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines". . p. 5360 - 5365. Retrieved 2015.
• 5、 Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald. "Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity". . p. 1667 - 1679. Retrieved 2021/03/24.
• 6、 Elkamhawy, Ahmed,Ammar, Usama M.,Paik, Sora,Abdellattif, Magda H.,Elsherbeny, Mohamed H.,Lee, Kyeong,Roh, Eun Joo. "Scaffold repurposing of in-house small molecule candidates leads to discovery of first-in-class cdk-1/her-2 dual inhibitors: In vitro and in silico screening". supporting information. . Retrieved 2021/09/08.