5-Methoxyindole

Base Information

• Chemical Name: 5-Methoxyindole
• CAS No.: 1006-94-6
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2933.90
• European Community (EC) Number: 213-745-3
• NSC Number: 521752
• UNII: DQM3AS43PQ
• DSSTox Substance ID: DTXSID80143424
• Nikkaji Number: J12.258K
• Wikidata: Q27276543
• ChEMBL ID: CHEMBL280311
• Mol file: 1006-94-6.mol

Synonyms:5-methoxy indole;5-methoxyindole

Chemical Property of 5-Methoxyindole

Chemical Property:

• Appearance/Colour: white to light brownish crystalline powder
• Vapor Pressure: 0.00234mmHg at 25°C
• Melting Point: 52-55 °C(lit.)
• Refractive Index: 1.637
• Boiling Point: 311.9 °C at 760 mmHg
• PKA: 16.70±0.30(Predicted)
• Flash Point: 109.2 °C
• PSA: 25.02000
• Density: 1.169 g/cm³
• LogP: 2.17650
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: insoluble
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99%, ^*data from raw suppliers

5-Methoxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2
• Uses: 5-Methoxyindole (cas# 1006-94-6) is a compound useful in organic synthesis. It can be used to synthesis 1-(Phenylsulfonyl)-5-methoxy-1H-indole.

Technology Process of 5-Methoxyindole

There total 92 articles about 5-Methoxyindole 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%

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → 5-methoxylindole (1006-94-6)

Guidance literature:

In quinoline; for 0.2h; microwave;

DOI:10.1021/jo00072a052

Reference yield: 99.0%

5-Methoxyindole-3-carboxylic acid (10242-01-0) → 5-methoxylindole (1006-94-6)

Guidance literature:

With potassium carbonate; In ethanol; at 140 ℃; Schlenk technique;

DOI:10.1080/00397911.2019.1703137

Reference yield: 99.0%

1-(5-methoxy-1H-indol-1-yl)-2,2-dimethylpropan-1-one (845619-77-4) → 5-methoxylindole (1006-94-6)

Guidance literature:

With water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 18h; Reflux;

DOI:10.1016/j.tet.2011.10.098

upstream raw materials:

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

5-benzyloxy-1H-indole

1-(5-methoxy-1H-indol-1-yl)ethan-1-one

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

Downstream raw materials:

1,3-diacetyl-2-(5-methoxyindol-3-yl)-4-imidazoline

5-methoxy-3-(2-pyridin-4-yl-ethyl)-indole

5-methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

5,5'-dimethoxy-3,3'-(1-methyl-piperidine-4,4-diyl)-bis-indole

Refernces

• 1、 Ruiz, Míriam,Sánchez, J. Domingo,López-Alvarado, Pilar,Menéndez, J. Carlos. "A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles". . p. 705 - 710. Retrieved 2012.
• 2、 Elavarasan, Samaraj,Bhaumik, Asim,Sasidharan, Manickam. "An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions". . p. 4340 - 4350. Retrieved 2019.
• 3、 Liu, Yugang,Shen, Lichun,Prashad, Mahavir,Tibbatts, Jessica,Repic, Oljan,Blacklock, Thomas J.. "A green N-detosylation of indoles and related heterocycles using phase transfer catalysis". . p. 778 - 780. Retrieved 2008.
• 4、 Black, Gary W.,Brancale, Andrea,Castagnolo, Daniele,Colonna, Serena,Ferla, Salvatore,Masci, Domiziana,Turner, Nicholas J.,Varricchio, Carmine,Zhao, Fei. "Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization". . p. 6414 - 6421. Retrieved 2020.
• 5、 Jones, Graham B.,Chapman, Brant J.. "Decarboxylation of Indole-2-carboxylic Acids: Improved Procedures". . p. 5558 - 5559. Retrieved 1993.
• 6、 Jaiswal, Garima,Subaramanian, Murugan,Sahoo, Manoj K.,Balaraman, Ekambaram. "A Reusable Cobalt Catalyst for Reversible Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles". . p. 2449 - 2457. Retrieved 2019.
• 7、 Cho, Chan Sik,Kim, Jin Hwang,Shim, Sang Chul. "Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium". . p. 1811 - 1814. Retrieved 2000.
• 8、 Wu, Jianjun,Talwar, Dinesh,Johnston, Steven,Yan, Ming,Xiao, Jianliang. "Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst". . p. 6983 - 6987. Retrieved 2013.
• 9、 Niu, Xiaokang,Yang, Lei. "Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline". . p. 4209 - 4215. Retrieved 2021.
• 10、 Marchant,Harvey. "-". . p. 1808,1810. Retrieved 1951.