3-Methylindole

Base Information

• Chemical Name: 3-Methylindole
• CAS No.: 83-34-1
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• Hs Code.: 2933.99
• European Community (EC) Number: 201-471-7
• NSC Number: 122024
• UNII: 9W945B5H7R
• DSSTox Substance ID: DTXSID8021775
• Nikkaji Number: J3.211E
• Wikipedia: Skatole
• Wikidata: Q412281
• NCI Thesaurus Code: C87586
• Metabolomics Workbench ID: 37262
• ChEMBL ID: CHEMBL1329793
• Mol file: 83-34-1.mol

Synonyms:3 Methylindole;3-Methylindole;Skatole

Chemical Property of 3-Methylindole

Chemical Property:

• Appearance/Colour: slightly brown platelets
• Vapor Pressure: 0.0153mmHg at 25°C
• Melting Point: 92-97 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 265.1 °C at 760 mmHg
• Flash Point: 112.5 °C
• PSA: 15.79000
• Density: 1.11 g/cm³
• LogP: 2.47630
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S36:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: CC1=CNC2=CC=CC=C12

Technology Process of 3-Methylindole

There total 247 articles about 3-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: 58.7%

1-methylindole (603-76-9) → indole (120-72-9) + 3-Methylindole (83-34-1) + 1,3-dimethylindole (875-30-9) + aniline (62-53-3)

Guidance literature:

With water; hydrogen; aluminum oxide; zinc(II) oxide; In benzene; at 550 ℃; under 760 Torr; Product distribution; other alkylindoles; var. catalysts and temp., var. gases, also in absence of benzene;

Reference yield: 56.4%

1-Bromo-2-iodobenzene (583-55-1) + 1-amino-2-propene (107-11-9,30551-89-4) → N-allyl-N-phenylamine (589-09-3) + 3-Methylindole (83-34-1)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 100 ℃; for 15h;

DOI:10.1002/anie.200703763

Reference yield: 50.0%

indole-3-carbinol (700-06-1) + cyanomethylene triphenylphosphorane (16640-68-9) → 3-Methylindole (83-34-1) + 1H-indole-3-propiononitrile (4414-76-0) + 3-indol-3-yl-acrylonitrile (21777-18-4)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In toluene; at 150 ℃; for 72h;

DOI:10.1002/ejoc.200600070

upstream raw materials:

indole

methanol

sodium methylate

1-phenylamino 2,3-propanediol

Downstream raw materials:

3-methyl-2-xanthen-9-yl-indole

(+/-)-3a-methyl-(3ar,8ac)-1,2,3,4a,8,8a-hexahydro-pyrrolo[2,3-b]indole

N-(2-acetylphenyl)formamide

3-methylindole-2-carboxylic acid

Refernces

• 1、 Roll, Deborah M.,Ireland, Chris M.. "CITORELLAMINE, A NEW BROMOINDOLE DERIVATIVE FROM POLYCITORELLA MARIAE". . p. 4303 - 4306. Retrieved 1985.
• 2、 Nakazaki,Yamamoto. "-". . p. 1877. Retrieved 1976.
• 3、 Chen, Yu,Xu, Chenghua,Liu, Chuanqi,Li, Xue,Liu, Jianying,Cao, Yang,Yang, Jie. "Synthesis of 3-methylindole from glycerol cyclization with aniline over CuCr/Al2O3 catalysts modified by alkali earth oxides". . p. 263 - 270. Retrieved 2013.
• 4、 Sun, Wei,Liu, Dong-Yan,Zhu, Hai-Yan,Shi, Lei,Sun, Qi. "A new efficient approach to 3-methylindole: Vapor-phase synthesis from aniline and glycerol over Cu-based catalyst". . p. 147 - 150. Retrieved 2010.
• 5、 Chatterjee,Biswas. "-". . p. 1257. Retrieved 1975.
• 6、 Arora, Pankaj Kumar,Dhar, Kartik,Veloz García, Rafael Alejandro,Sharma, Ashutosh. "Biotransformation of Indole to 3-Methylindole by Lysinibacillus xylanilyticus Strain MA". . . Retrieved 2015.
• 7、 Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo. "Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations". supporting information. p. 7738 - 7744. Retrieved 2021/05/07.
• 8、 Xie, Tao,Sui, Qi-Bang,Qin, Lu-Zhe,Wen, Xiaoan,Sun, Hongbin,Xu, Qing-Long,Zhen, Le. "Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles". supporting information. p. 5518 - 5529. Retrieved 2021/05/04.