1-(5-chloro-1H-indol-3-yl)ethanone

Base Information

• Chemical Name: 1-(5-chloro-1H-indol-3-yl)ethanone
• CAS No.: 51843-24-4
• Molecular Formula: C10H8 Cl N O
• Molecular Weight: 193.633
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10376622
• Wikidata: Q72434953
• Mol file: 51843-24-4.mol

Synonyms:1-(5-chloro-1H-indol-3-yl)ethanone;51843-24-4;3-Acetyl-5-chloroindole;1-(5-chloro-1H-indol-3-yl)ethan-1-one;SCHEMBL5912617;AMY2888;DTXSID10376622;LEUBXJIHEAWOHZ-UHFFFAOYSA-N;MFCD07437837;AKOS013193404;DS-1417;FS-3420;CS-0042988;FT-0657641;1-(5-Chloro-1H-indol-3-yl)ethanone, AldrichCPR;A828811

Chemical Property of 1-(5-chloro-1H-indol-3-yl)ethanone

Chemical Property:

• Vapor Pressure: 1.32E-05mmHg at 25°C
• Melting Point: 168 °C (decomp)(Solv: ethyl ether (60-29-7))
• Boiling Point: 367.9°C at 760 mmHg
• PKA: 14.46±0.30(Predicted)
• Flash Point: 176.3°C
• PSA: 32.86000
• Density: 1.332
• LogP: 3.02390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 193.0294416
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

98%Min ^*data from raw suppliers

1-(5-Chloro-1H-indol-3-yl)ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CNC2=C1C=C(C=C2)Cl

Technology Process of 1-(5-chloro-1H-indol-3-yl)ethanone

There total 9 articles about 1-(5-chloro-1H-indol-3-yl)ethanone 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: 91.0%

5-chloro-1H-indole (17422-32-1) + acetyl chloride (75-36-5) → 1-(5-chloro-1H-indol-3-yl)ethan-1-one (51843-24-4)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jm050549e

Reference yield: 84.0%

5-chloro-1H-indole (17422-32-1) + acetic anhydride (108-24-7) → 1-(5-chloro-1H-indol-3-yl)ethan-1-one (51843-24-4)

Guidance literature:

With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate; In neat (no solvent); at 100 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1039/c7ra11362e

Reference yield: 62.0%

→ 1-(5-chloro-1H-indol-3-yl)ethan-1-one (51843-24-4)

Guidance literature:

With chlorine; tin(IV) chloride; In tetrachloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

In tetrachloromethane; Inert atmosphere;

upstream raw materials:

5-chloro-1H-indole

acetic anhydride

acetyl chloride

5-chloro-1H-Indole-2-carboxylic acid

Downstream raw materials:

4-[1-(3,5-dimethylbenzyl)-5-chloro-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid

4-[1-(2,4,6-trimethylbenzyl)-5-chloro-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid

C₂₆H₁₈ClNO₄

C₂₁H₁₃ClF₃NO₄

Refernces

• 1、 Jiang, Zhidong,Liu, Hong,Zhou, Jianhui,Zhou, Yu,Zhu, Haoran. "Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles". supporting information. p. 4406 - 4410. Retrieved 2021/06/28.
• 2、 -. "Natural product Pimprinine derivative as well as preparation method and application thereof". Paragraph 0079-0082; 0084. . Retrieved 2021/07/31.