methyl 2-(4-chloro-1H-indol-3-yl)acetate

Base Information

• Chemical Name: methyl 2-(4-chloro-1H-indol-3-yl)acetate
• CAS No.: 19077-78-2
• Molecular Formula: C11H10 Cl N O2
• Molecular Weight: 223.659
• Hs Code.: 2933990090
• UNII: J94KP69SZB
• DSSTox Substance ID: DTXSID20172571
• Nikkaji Number: J662I
• Wikidata: Q27281365
• Metabolomics Workbench ID: 45797
• Mol file: 19077-78-2.mol

Synonyms:4-chloroindolyl-3-acetic acid methyl ester;methyl 4-chloroindolyl-3-acetate

Chemical Property of methyl 2-(4-chloro-1H-indol-3-yl)acetate

Chemical Property:

• Vapor Pressure: 8.35E-06mmHg at 25°C
• Boiling Point: 374.4°Cat760mmHg
• PKA: 15.76±0.30(Predicted)
• Flash Point: 180.3°C
• PSA: 42.09000
• Density: 1.342g/cm³
• LogP: 2.53680
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 223.0400063
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

4-Chloroindole-3-aceticAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1=CNC2=C1C(=CC=C2)Cl
• Uses: 4-Chloroindole-3-acetic Acid Methyl Ester can be used in biological study for metabolism and bioactivity of 4-chloroindole-3-acetic acid in plants. It can also be used as reagent/reactant for interpretation of mass spectral characteristic fragmentation mechanisms of indole alkaloids through determining initial ionization site.

Technology Process of methyl 2-(4-chloro-1H-indol-3-yl)acetate

There total 6 articles about methyl 2-(4-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: 73.5%

methanol (67-56-1) + 4-chloroindole-3-acetic acid (2519-61-1) → Methyl 4-chloro-3-indoleacetate (19077-78-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2h;

DOI:10.1271/bbb.64.808

Reference yield:

4-chloro-1H-indole (25235-85-2) → Methyl 4-chloro-3-indoleacetate (19077-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 72.2 percent / acetic acid / 5 - 20 °C

2: 87.3 percent / dimethylformamide; H₂O / 6 h / Heating

3: 94.1 percent / aq. potassium hydroxide / methanol / 16 h / Heating

4: 73.5 percent / N,N'-dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

With dmap; potassium hydroxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Esterification;

DOI:10.1271/bbb.64.808

Reference yield:

6-chloro-2-nitrotoluene (83-42-1) → Methyl 4-chloro-3-indoleacetate (19077-78-2)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylformamide / 80 h / 110 °C

2: 243.3 g / aq. hydrazine hydrate / tetrahydrofuran; methanol / 10 - 20 °C

3: 72.2 percent / acetic acid / 5 - 20 °C

4: 87.3 percent / dimethylformamide; H₂O / 6 h / Heating

5: 94.1 percent / aq. potassium hydroxide / methanol / 16 h / Heating

6: 73.5 percent / N,N'-dicyclohexylcarbodiimide; N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

With dmap; potassium hydroxide; hydrazine hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Substitution / 4: Substitution / 5: Hydrolysis / 6: Esterification;

DOI:10.1271/bbb.64.808

upstream raw materials:

methanol

4-chloroindole-3-acetic acid

4-chloro-1H-indole

6-chloro-2-nitrotoluene

Downstream raw materials:

Indole-3-acetic acid methyl ester

(1H-Indol-3-yl)-{3-[1-methoxycarbonyl-meth-(E)-ylidene]-2,3-dihydro-1H-indol-2-yl}-acetic acid methyl ester

Refernces