4-methoxy-1H-indole-3-carbaldehyde

Base Information

• Chemical Name: 4-methoxy-1H-indole-3-carbaldehyde
• CAS No.: 90734-97-7
• Molecular Formula: C10H8NO2
• Molecular Weight: 175.187
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50238250
• Nikkaji Number: J1.523.577B
• Wikidata: Q63393178
• Mol file: 90734-97-7.mol

Synonyms:4-methoxyindole-3-aldehyde

Chemical Property of 4-methoxy-1H-indole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 7.89E-06mmHg at 25°C
• Melting Point: 162-163 °C
• Refractive Index: 1.679
• Boiling Point: 375.2 °C at 760 mmHg
• PKA: 15.73±0.30(Predicted)
• Flash Point: 180.7 °C
• PSA: 42.09000
• Density: 1.273 g/cm³
• LogP: 1.98900
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

98%min ^*data from raw suppliers

4-Methoxyindole-3-carboxaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C(=CN2)C=O
• Uses: 4-Methoxy-3-indolecarboxaldehyde is a nitrosatable mutagen precursor found in Chinese cabbage.

Technology Process of 4-methoxy-1H-indole-3-carbaldehyde

There total 22 articles about 4-methoxy-1H-indole-3-carbaldehyde 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%

4-methoxy-1H-indole (4837-90-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-methoxyindole-3-carboxaldehyde (90734-97-7)

Guidance literature:

N,N-dimethyl-formamide; With N-chloro-succinimide; triphenylphosphine; In tetrahydrofuran; for 1h; Reflux;

4-methoxy-1H-indole; In tetrahydrofuran; for 1h; Reflux;

DOI:10.1021/jm800689g

Reference yield: 99.0%

1-(2,2-dimethyl-propionyl)-4-methoxy-1H-indole-3-carbaldehyde → 4-methoxyindole-3-carboxaldehyde (90734-97-7)

Guidance literature:

With polymer-supported potassium thiophenolate; In tetrahydrofuran; methanol; at 40 ℃;

DOI:10.1055/s-2004-817786

Reference yield: 95.0%

4-methoxy-1H-indole (4837-90-5) + oxalyl dichloride (79-37-8) → 4-methoxyindole-3-carboxaldehyde (90734-97-7)

Guidance literature:

oxalyl dichloride; With N,N-dimethyl-formamide; In 1,2-dichloro-ethane;

4-methoxy-1H-indole; In 1,2-dichloro-ethane; at 20 ℃; for 4h;

upstream raw materials:

Indole-3-carboxaldehyde

sodium methylate

4-methoxy-1H-indole

N,N-dimethyl-formamide

Downstream raw materials:

4-methoxytryptamine

N-tert-butoxycarbonyl-4-methoxyindole-3-carboxaldehyde

(+)-mitragynine

methyl (Z)-2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate

Refernces

• 1、 Pedras, M. Soledade C.,Hossain, Sajjad. "Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are". . p. 2308 - 2316. Retrieved 2011.
• 2、 Zhu, Yu-Rong,Lin, Jin-Hong,Xiao, Ji-Chang. "Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide". supporting information. p. 259 - 263. Retrieved 2021/11/22.
• 3、 Ma, Jinhui,Luo, Jiajun,Jiang, Kai,Zhang, Guangwen,Liu, Shubin,Yin, Biaolin. "Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S". supporting information. p. 8033 - 8038. Retrieved 2021/10/25.