cyclopropyl(1H-indol-3-yl)methanone

Base Information

• Chemical Name: cyclopropyl(1H-indol-3-yl)methanone
• CAS No.: 675834-79-4
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.225
• DSSTox Substance ID: DTXSID00359484
• Wikidata: Q82140712
• Mol file: 675834-79-4.mol

Synonyms:cyclopropyl(1H-indol-3-yl)methanone;675834-79-4;3-CYCLOPROPANECARBONYL-1H-INDOLE;SCHEMBL17025733;DTXSID00359484;ILBLOQDDOYEESV-UHFFFAOYSA-N;CHEMBRDG-BB 9070714;MFCD04343914;STL371403;AKOS000343266;CCG-357246;AS-35466;CS-0199751;A915700

Chemical Property of cyclopropyl(1H-indol-3-yl)methanone

Chemical Property:

• Vapor Pressure: 6.77E-06mmHg at 25°C
• Boiling Point: 377.4°C at 760 mmHg
• Flash Point: 189.4°C
• Density: 1.298g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 185.084063974
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C(=O)C2=CNC3=CC=CC=C32

Technology Process of cyclopropyl(1H-indol-3-yl)methanone

There total 2 articles about cyclopropyl(1H-indol-3-yl)methanone 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: 49.0%

indole (120-72-9) + 2-cyclopropyl-2-oxoacetic acid (13885-13-7) → cyclopropyl(1H-indol-3-yl)methanone (675834-79-4)

Guidance literature:

With rose bengal; In ethanol; at 20 ℃; for 10h; regioselective reaction; Molecular sieve; Irradiation;

DOI:10.1039/c6gc00516k

Reference yield:

indole (120-72-9) + cyclopropanecarboxylic acid chloride (4023-34-1) → cyclopropyl(1H-indol-3-yl)methanone (675834-79-4)

Guidance literature:

indole; With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃; for 0.5h;

cyclopropanecarboxylic acid chloride; In nitromethane; dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jacs.6b13031

Reference yield:

cyclopropyl(1H-indol-3-yl)methanone (675834-79-4) → (E)-(1-benzyl-4-(phenylthio)-1H-indol-3-yl)(cyclopropyl)methanone O-methyl oxime

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C

1.2: 20 °C

2.1: sodium acetate / ethanol; water / 70 °C

3.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; silver(l) oxide; copper diacetate / 40 °C

With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; sodium acetate; sodium hydride; silver(l) oxide; In tetrahydrofuran; ethanol; water; mineral oil;

DOI:10.1039/c7cc07086a

upstream raw materials:

indole

2-cyclopropyl-2-oxoacetic acid

cyclopropanecarboxylic acid chloride