Methyl indole-1-carboxylate

Base Information

• Chemical Name: Methyl indole-1-carboxylate
• CAS No.: 39203-20-8
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933998090
• European Community (EC) Number: 622-994-0
• DSSTox Substance ID: DTXSID10494193
• Nikkaji Number: J1.074.965D
• Wikidata: Q82341371
• Mol file: 39203-20-8.mol

Synonyms:39203-20-8;Methyl indole-1-carboxylate;Methyl 1H-indole-1-carboxylate;Indole-1-carboxylic acid methyl ester;N-methoxycarbonylindole;methyl 2-(indol-1-yl)acetate;MFCD11656094;N-(Methoxycarbonyl)indole;SCHEMBL1173678;DTXSID10494193;FHOPBCYBMWVMGJ-UHFFFAOYSA-N;Methyl indole-1-carboxylate, 97%;AKOS015904620;SY185804;CS-0195890;E90566

Chemical Property of Methyl indole-1-carboxylate

Chemical Property:

• Refractive Index: n20/D 1.583
• Flash Point: 100?°C
• PSA: 31.23000
• Density: 1.191?g/mL?at 25?°C
• LogP: 2.25580
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

methyl2-(1H-indol-1-yl)acetate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)N1C=CC2=CC=CC=C21
• Uses: ? ;Reactant for preparation of Bcl Inhibitor Obatoclax1? ;Reactant for preparation of tetracyclic indolines2? ;Reactant for Friedel-Crafts alkylation reaction of indoles3? ;Reactant for oxidative free radical reactions4 Reactant for preparation of Bcl Inhibitor ObatoclaxReactant for preparation of tetracyclic indolinesReactant for Friedel-Crafts alkylation reaction of indolesReactant for oxidative free radical reactions

Technology Process of Methyl indole-1-carboxylate

There total 6 articles about Methyl indole-1-carboxylate 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: 36.0%

methyl 2-vinylaniline-N-carboxylate (23206-21-5) + lead(IV) tetraacetate (546-67-8) → methyl 1H-indole-1-carboxylate (39203-20-8) + 2-{2-[(methoxycarbonyl)amino]phenyl}ethane-1,1-diyl diacetate

Guidance literature:

In dichloromethane; at 20 ℃; for 15h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.1c01379

Reference yield: 23.0%

indole (120-72-9) + methyl chloroformate (79-22-1) → methyl 1H-indole-1-carboxylate (39203-20-8) + N-methoxycarbonyl-2-[2,2-bis-(1H-indol-3-yl)ethyl]phenylamine (1161939-83-8) + 1-Carbomethoxy-2,3-dihydro-2,3'-diindole (94512-22-8)

Guidance literature:

With tert-butylamine; In dichloromethane; at 5 - 20 ℃;

DOI:10.3987/COM-08-11627

Reference yield:

indole (120-72-9) + carbonic acid dimethyl ester (616-38-6) → 1-methylindole (603-76-9) + methyl 1H-indole-1-carboxylate (39203-20-8)

Guidance literature:

With tri-n-butylmethylammonium methylcarbonate; In N,N-dimethyl-formamide; at 190 ℃; for 0.166667h; Reagent/catalyst; Temperature; Time; Microwave irradiation;

DOI:10.1039/c2gc36226k

upstream raw materials:

N-(methoxycarbonyl)-2-vinylformanilide

indole

methyl chloroformate

carbonic acid dimethyl ester

Downstream raw materials:

2-aza-3,4-benzo-N-carbmethoxy-bicyclo-<3.1.0>hex-3-ene

3-Phenyl-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid methyl ester

3-(2,4,6-Trimethyl-phenyl)-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid methyl ester

3-(2,4,6-Trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indole-4-carboxylic acid methyl ester

Refernces

• 1、 Glasnov, Toma N.,Kappe, C. Oliver,Holbrey, John D.,Seddon, Kenneth R.,Yan, Ting. "Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions". . p. 3071 - 3076,6. Retrieved 2020/09/16.
• 2、 Bennasar, M. Lluisa,Roca, Tomas,Monerris, Manuel,Garcia-Diaz, Davinia. "Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles". . p. 7028 - 7034. Retrieved 2007/10/03.