5-Methoxy-2-methylindole

Base Information

• Chemical Name: 5-Methoxy-2-methylindole
• CAS No.: 1076-74-0
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• Hs Code.: 29339900
• European Community (EC) Number: 214-066-5
• NSC Number: 63817
• DSSTox Substance ID: DTXSID20148115
• Nikkaji Number: J113.030G
• Wikidata: Q63395477
• ChEMBL ID: CHEMBL4850447
• Mol file: 1076-74-0.mol

Synonyms:5-Methoxy-2-methylindole;1076-74-0;5-Methoxy-2-methyl-1H-indole;2-Methyl-5-methoxyindole;1H-Indole, 5-methoxy-2-methyl-;Indole, 5-methoxy-2-methyl-;MFCD00005620;nsc 63817;CHEMBL4850447;EINECS 214-066-5;NSC63817;5-methoxy-2-methyindole;Maybridge1_002343;5-Methoxy-2 methylindole;2-methyl-5-methoxylindole;2-methyl-5-methoxy indole;5-methoxy-2-methyl indole;5-methoxy-2-methyl-indole;NCIOpen2_000130;SCHEMBL74023;DivK1c_001095;HMS548C11;VSWGLJOQFUMFOQ-UHFFFAOYSA-;DTXSID20148115;5-Methoxy-2-methylindole, 99%;CHEBI:194945;AM689;KUC107903N;5-Methoxy-2-methyl-1H-indole #;BBL104417;BDBM50578092;CCG-51145;NSC-63817;STK504142;AKOS004116677;CS-W008520;KSC-09-236;SB15294;CDS1_000055;NCGC00188230-01;NCGC00188230-02;NCGC00188230-03;AC-23427;AS-19488;BP-10441;BB 0262629;FT-0620558;M0730;EN300-77547;M-3530;SR-01000640461-1;Q63395477;Z1197882538;CWJ

Chemical Property of 5-Methoxy-2-methylindole

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 0.00123mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Refractive Index: 1.621
• Boiling Point: 308.501 °C at 760 mmHg
• PKA: 17.28±0.30(Predicted)
• Flash Point: 113.125 °C
• PSA: 25.02000
• Density: 1.134 g/cm³
• LogP: 2.48490
• Storage Temp.: 0-6°C
• Solubility.: Soluble in methanol (very faint turbidity.)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxy-2-methylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(N1)C=CC(=C2)OC
• Description: 5-methoxy-2-methylindole is a useful organic raw material. It can be used as the reactant in the preparation of indolylquinoxalines by condensation reactions, in preparation of alkylindoles via Ir-catalyzed reductive alkylation, in arylation reactions in the presence of a palladium acetate catalyst, in enantioselective Friedel-Crafts alkylation, as well as in stereo selective synthesis of cyclopentaindolones via stereoselective [3+2] cyclopentannulation. It is also employed in inhibiting the chlorinating activity of myeloperoxidase (MPO) and in the metabolic synthesis of acrylacetic acid anti-inflammatory synthesis.
• Uses: An indole derivative shown to be an effective inhibitor of the chlorinating activity of myeloperoxidase (MPO). Used in the metabolic synthesis of arylacetic acid antiinflammatory synthesis. reactant in preparation of indolylquinoxalines by condensation reactions1reactant in preparation of alkylindoles via Ir-catalyzed reductive alkylation2reactant in arylation reactions using a palladium acetate catalyst3reactant in enantioselective Friedel-Crafts alkylation4reactant in stereoselective synthesis of cyclopentaindolones via stereoselective [3+2] cyclopentannulation5 It is employed as a reactant in preparation of indolylquinoxalines by condensation reactions, reactant in preparation of alkylindoles via Ir-catalyzed reductive alkylation, reactant in arylation reactions using a palladium acetate catalyst, reactant in enantioselective Friedel-Crafts alkylation and reactant in stereoselective synthesis of cyclopentaindolones via stereoselective [3+2] cyclopentannulation. As an indole derivative shown to be an effective inhibitor of the chlorinating activity of myeloperoxidase (MPO). Used in the metabolic synthesis of arylacetic acid anti-inflammatory synthesis.

Technology Process of 5-Methoxy-2-methylindole

There total 42 articles about 5-Methoxy-2-methylindole 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%

methyl 5-methoxy-2-methyl-1H-indole-1-carboxylate → 5-methoxy-2-methyl-1H-indole (1076-74-0)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Reflux;

DOI:10.1021/acs.joc.8b01999

Reference yield: 97.0%

bromure d'acetylamino-2 methoxy-5 benzyltriphenylphosphonium (104894-18-0) → 5-methoxy-2-methyl-1H-indole (1076-74-0)

Guidance literature:

With potassium tert-butylate; In toluene; for 0.25h; Heating;

DOI:10.1016/S0040-4020(01)96783-3

Reference yield: 96.0%

5-methoxy-2-methyl-3-(phenylthio)-1H-indole (98055-12-0) → 5-methoxy-2-methyl-1H-indole (1076-74-0)

Guidance literature:

With thiosalicilyc acid; In trifluoroacetic acid; for 1.5h; Ambient temperature;

DOI:10.1021/jo00100a045

upstream raw materials:

5-methoxy-2methyl-1H-indole-3-carboxylic acid

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

acetone(4-methoxyphenyl)hydrazone

ethyl 5-methoxy-2-methyl-1H-indole-3-carboxylate

Downstream raw materials:

1-(5-methoxy-2-methyl-indol-3-yl)-2-phenyl-ethanone

2-Methyl-5-methoxy-gramin

5-methoxy-2-methyl-1H-indole-3-carbaldehyde

5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole

Refernces

• 1、 Caubere,Caubere,Renard,Bizot-Espiart,Jamart-Gregoire. "Complex bases promoted arynic cyclisations of halogenated imines or enamines: A regiochemical synthesis of indole derivatives". . p. 6889 - 6892. Retrieved 1993.
• 2、 Gassman et al.. "-". . p. 6508. Retrieved 1973.
• 3、 -. "Process for preparing 5-methoxy-2-methylindole". Paragraph 0035-0041; 0049-0054; 0062-0067. . Retrieved 2020/07/02.
• 4、 Ren, Long,Nan, Guanglei,Wang, Yongcheng,Xiao, Zhiyan. "Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling". . p. 14472 - 14488. Retrieved 2018/11/23.