2-Methylindoline

Base Information

• Chemical Name: 2-Methylindoline
• CAS No.: 6872-06-6
• Deprecated CAS: 138380-84-4
• Molecular Formula: C9H11N
• Molecular Weight: 133.193
• Hs Code.: 29349990
• European Community (EC) Number: 229-971-0
• NSC Number: 65598
• UNII: 5GAL2SM4VV
• DSSTox Substance ID: DTXSID70884339
• Nikkaji Number: J8.853F
• Wikidata: Q27262116
• Metabolomics Workbench ID: 71528
• Mol file: 6872-06-6.mol

Synonyms:2-Methylindoline;6872-06-6;2-methyl-2,3-dihydro-1H-indole;2,3-Dihydro-2-methylindole;1H-Indole, 2,3-dihydro-2-methyl-;2-Methyl-2,3-dihydroindole;Indoline, 2-methyl-;Dihydroindole, 2-methyl-;alpha-Methyldihydroindole;2,3-DIHYDRO-2-METHYL-1H-INDOLE;PE-11;NSC 65598;5GAL2SM4VV;.alpha.-Methyldihydroindole;2-methyl indoline;EINECS 229-971-0;MFCD00005706;NSC-65598;BRN 0081505;2-methyl-indoline;NSC65598;a-Methyldihydroindole;UNII-5GAL2SM4VV;2-Methylindoline, 98%;NCIOpen2_000227;SCHEMBL33268;SCHEMBL12837999;1H-Indole,3-dihydro-2-methyl-;DTXSID70884339;CHEBI:166548;STR07895;STL124108;AKOS000119057;AKOS016356737;CS-W013390;PS-3274;SB15111;SB15112;SB15113;(2R)-2,3-dihydro-2-methyl-1H-Indole;AC-28908;LS-83460;SY014921;A9135;M0871;EN300-19044;D71186;5-20-06-00344 (Beilstein Handbook Reference);J-510060;Q27262116;F2190-0414;Z104472410

Chemical Property of 2-Methylindoline

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 0.0585mmHg at 25°C
• Melting Point: -51 °C
• Refractive Index: n20/D 1.569(lit.)
• Boiling Point: 232.6 °C at 760 mmHg
• PKA: 5.26±0.40(Predicted)
• Flash Point: 93.3 °C
• PSA: 12.03000
• Density: 0.989 g/cm³
• LogP: 2.18110
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform, Methanol
• Water Solubility.: negligible
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2-Methylindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-22
• Safety Statements: 26-36/37/39-60-57

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC=CC=C2N1
• Uses: 2-Methylindoline is an intermediate in the production of various indole derivatives Reactant for preparation of:Inhibitors of NOD1-induced nuclear factor-κB activationRed fluorescent dyes for organic light-emitting diodesNorepinephrine reuptake inhibitorsMT2-selective melatonin receptor antagonistsProtease-activated receptor-1 antagonistsDiuretic agent indapamideDopamine D2/D4 receptor antagonistsAntitumor agents

Technology Process of 2-Methylindoline

There total 43 articles about 2-Methylindoline 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%

2-methyl-1H-indole (95-20-5) → 2-methyl indoline (6872-06-6)

Guidance literature:

With tetrahydroxydiboron; palladium on activated carbon; In 2,2,2-trifluoroethanol; water; at 40 ℃; for 24h; Schlenk technique;

DOI:10.1039/d0ob02080j

Reference yield: 94.0%

2-allyl-phenylamine (32704-22-6) → 2-methyl indoline (6872-06-6)

Guidance literature:

With C₄₈H₆₆N₂O₂Zr^(2-); trityl tetrakis(pentafluorophenyl)borate; In chlorobenzene; at 140 ℃; for 48h; Glovebox; Inert atmosphere;

DOI:10.1039/c5ra23270h

Reference yield: 93.0%

2-(prop-2-yn-1-yl)aniline (1534360-76-3) → 2-methyl indoline (6872-06-6)

Guidance literature:

With C₃₃H₆₃N₁₅Zr₃; In toluene; at 140 ℃; for 48h; Glovebox; Inert atmosphere;

DOI:10.1002/zaac.201800109

upstream raw materials:

2-methyl-1H-indole

2-allyl-phenylamine

tert-Butyl-[1-(2-methyl-2,3-dihydro-indol-1-yl)-meth-(E)-ylidene]-amine

ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate

Downstream raw materials:

1-(2-methyl-2,3-dihydro-indol-1-yl)-ethanone

(2-methylindolin-1-yl)(phenyl)methanone

1,1,2-trimethyl-indolinium; iodide

1,2-dimethylindoline

Refernces

• 1、 Venkataramu et al.. "-". . p. 2195,2198,2199. Retrieved 1977.
• 2、 Zhou, Xiao-Yu,Chen, Xia. "Pd/C-Catalyzed transfer hydrogenation ofN-H indoles with trifluoroethanol and tetrahydroxydiboron as the hydrogen source". supporting information. p. 548 - 551. Retrieved 2021/02/06.
• 3、 Agbossou-Niedercorn, Francine,Corre, Yann,Dongare, Mohan K.,Kemnitz, Erhard,Kokane, Reshma,Michon, Christophe,Umbarkar, Shubhangi B.. "Palladium supported on magnesium hydroxyl fluoride: An effective acid catalyst for the hydrogenation of imines and N-heterocycles". supporting information. p. 19572 - 19583. Retrieved 2021/11/04.