1,2-Dimethylindole

Base Information

• Chemical Name: 1,2-Dimethylindole
• CAS No.: 875-79-6
• Molecular Formula: C10H11N
• Molecular Weight: 145.204
• Hs Code.: 2933.99
• European Community (EC) Number: 212-877-9
• NSC Number: 62087
• UNII: H373TS720O
• DSSTox Substance ID: DTXSID00236367
• Nikkaji Number: J26.025H
• Wikidata: Q27279585
• ChEMBL ID: CHEMBL3252124
• Mol file: 875-79-6.mol

Synonyms:1,2-DIMETHYLINDOLE;875-79-6;1,2-Dimethyl-1H-indole;N-Methyl-2-methylindole;1H-Indole, 1,2-dimethyl-;Indole, 1,2-dimethyl-;MFCD00005802;1.2-Dimethylindole;1,2-dimethyl indole;UNII-H373TS720O;H373TS720O;EINECS 212-877-9;NSC 62087;NSC-62087;dimethyl-1H-indole;1H-Indole,2-dimethyl-;1,2-Dimethylindole, 99%;SCHEMBL154592;CHEMBL3252124;BJMUOUXGBFNLSN-UHFFFAOYSA-;DTXSID00236367;NSC62087;STK301478;AKOS003791088;CS-W010998;SB14858;AC-28904;AS-14361;SY004658;D1391;FT-0606420;3-AMINO-2-(3-BROMOBENZYL)PROPIONICACID;D-5348;EN300-136093;A842280;Q27279585

Chemical Property of 1,2-Dimethylindole

Chemical Property:

• Appearance/Colour: off-white powder or crystals
• Vapor Pressure: 0.0198mmHg at 25°C
• Melting Point: 55-58 °C(lit.)
• Refractive Index: 1.561
• Boiling Point: 260.5 °C at 760 mmHg
• Flash Point: 111.3 °C
• PSA: 4.93000
• Density: 0.99 g/cm³
• LogP: 2.48670
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 145.089149355
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dimethyl-1H-indole ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: CC1=CC2=CC=CC=C2N1C
• General Description: 1,2-Dimethylindole is a substituted indole derivative that participates in platinum(II)-catalyzed hydroarylation reactions with unactivated alkenes such as ethylene, yielding products like 3-ethyl-1,2-dimethylindole. It demonstrates reactivity under mild conditions with good functional group tolerance, making it a useful substrate in synthetic organic chemistry for constructing alkylated indole frameworks.

Technology Process of 1,2-Dimethylindole

There total 71 articles about 1,2-Dimethylindole 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: 98.2%

2-methyl-1H-indole (95-20-5) + carbonic acid dimethyl ester (616-38-6) → 1,2-dimethylindole (875-79-6)

Guidance literature:

With tetrabutyl-ammonium chloride; potassium carbonate; In N,N-dimethyl-formamide; at 95 ℃; for 12h;

Reference yield: 98.0%

1,2-dimethylindoline (26216-93-3,174311-38-7) → 1,2-dimethylindole (875-79-6)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; In para-xylene; at 130 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c01905

Reference yield: 97.0%

2-methyl-1H-indole (95-20-5) + methyl iodide (74-88-4) → 1,2-dimethylindole (875-79-6)

Guidance literature:

2-methyl-1H-indole; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

DOI:10.1021/jm0204035

upstream raw materials:

2-methyl-1H-indole

methyl iodide

1-methylindole

(E)-3-Ureido-but-2-enoic acid ethyl ester

Downstream raw materials:

1,2-dimethyl-3-(2-nitro-1-phenyl-ethyl)-indole

1-(1,2-dimethyl-1H-indol-3-yl)ethanone

(1,2-dimethyl-indol-3-yl)-glyoxylic acid dimethylamide

1,2-dimethyl-1H-indole-3-carbaldehyde

Refernces

Platinum(II)-catalyzed intermolecular hydroarylation of unactivated alkenes with indoles

10.1039/b607286k

The study explores the platinum(II)-catalyzed intermolecular hydroarylation of unactivated alkenes with indoles. The researchers discovered that ethylene, α-olefins, and vinyl arenes can undergo hydroarylation with substituted indoles in moderate to good yields using platinum(II) complexes as catalysts. The key chemicals involved include 1,2-dimethylindole, which reacts with ethylene under the catalysis of [PtCl2(H2CLCH2)]2 to produce 3-ethyl-1,2-dimethylindole. The study also examines the hydroarylation of α-olefins like propene and 1-butene, as well as vinyl arenes such as p-chlorostyrene, with indoles. The platinum(II) catalysts enable these reactions to proceed efficiently, even with various substituents on the indole ring, demonstrating good functional group compatibility and selectivity. The study highlights the potential for further development of more active and selective hydroarylation catalysts, contributing to the field of organic synthesis.