5-chloro-1H-indol-3-yl acetate

Base Information

• Chemical Name: 5-chloro-1H-indol-3-yl acetate
• CAS No.: 114306-00-2
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.632
• European Community (EC) Number: 820-916-1
• Mol file: 114306-00-2.mol

Synonyms:3-Acetyloxy-5-chloroindole;114306-00-2;5-chloro-1H-indol-3-yl acetate;(5-chloro-1H-indol-3-yl) acetate;1H-Indol-3-ol, 5-chloro-, 3-acetate;SCHEMBL9120206;5-chloro-1H-indol-3-ylacetate;AKOS015961051;AB16769;AC-12761;CS-0260887;EN300-76233;J-003079

Chemical Property of 5-chloro-1H-indol-3-yl acetate

Chemical Property:

• Vapor Pressure: 9.5E-06mmHg at 25°C
• Refractive Index: 1.642
• Boiling Point: 372.6°Cat760mmHg
• Flash Point: 179.1°C
• PSA: 42.09000
• Density: 1.384g/cm³
• LogP: 2.74660
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 209.0243562
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%min ^*data from raw suppliers

5-CHLORO-3-METHYLPEROXYINDOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CNC2=C1C=C(C=C2)Cl

Technology Process of 5-chloro-1H-indol-3-yl acetate

There total 5 articles about 5-chloro-1H-indol-3-yl acetate 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: 87.1%

1,3-diacetyl-5-chloroindol + acetic anhydride (108-24-7) → 3-acetoxy-5-chloroindole (114306-00-2)

Guidance literature:

1,3-diacetyl-5-chloroindol; With sodium hydroxide; for 0.5h; Inert atmosphere; Reflux;

acetic anhydride; at 0 ℃; Inert atmosphere;

DOI:10.24820/ARK.5550190.P011.380

Reference yield:

5-chloro-1H-indole (17422-32-1) + silver(I) acetate (563-63-3) → 3-acetoxy-5-chloroindole (114306-00-2)

Guidance literature:

5-chloro-1H-indole; With iodine; potassium iodide; sodium hydroxide; In methanol; Inert atmosphere;

silver(I) acetate; With acetic acid; In methanol; Inert atmosphere;

DOI:10.1021/ol400055v

Reference yield:

5-chloro-1H-indole (17422-32-1) → 3-acetoxy-5-chloroindole (114306-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; iodine; potassium iodide / methanol; water / 3 h / 20 °C

2: acetic acid / 1 h / 90 °C

With iodine; acetic acid; potassium iodide; sodium hydroxide; In methanol; water;

DOI:10.1039/c5tc01023c

upstream raw materials:

1-acetyl-5-chloro-1H-indol-3-yl acetate

5-chloro-1H-indole

silver(I) acetate

3-iodo-5-chloro-1H-indole

Downstream raw materials:

5,5'-dichloroindigo

Refernces

• 1、 Pfretzschner, Alexander T.,Unverzagt, Carlo. "Total Synthesis of the Chlorinated Indigo-N-Glycosides Akashin A, B and C". supporting information. p. 206 - 229. Retrieved 2021/03/22.