1H-Indole-3-carboxylic acid, 2-chloro-1-methyl-

Base Information

• Chemical Name: 1H-Indole-3-carboxylic acid, 2-chloro-1-methyl-
• CAS No.: 54778-21-1
• Molecular Formula: C10H8ClNO2
• Molecular Weight: 209.632
• NSC Number: 234526
• DSSTox Substance ID: DTXSID10203247
• Nikkaji Number: J1.650.002J
• Wikidata: Q83076601
• ChEMBL ID: CHEMBL3277791
• Mol file: 54778-21-1.mol

Synonyms:54778-21-1;2-Chloro-1-methyl-1H-indole-3-carboxylic acid;1H-Indole-3-carboxylic acid, 2-chloro-1-methyl-;2-chloro-1-methylindole-3-carboxylic acid;BRN 0476383;NSC234526;SCHEMBL4658577;CHEMBL3277791;DTXSID10203247;AQPMLAXHNBHLTF-UHFFFAOYSA-N;AKOS004902209;NSC 234526;NSC-234526;FT-0703874;EN300-110119

Chemical Property of 1H-Indole-3-carboxylic acid, 2-chloro-1-methyl-

Chemical Property:

• Vapor Pressure: 2.23E-07mmHg at 25°C
• Refractive Index: 1.631
• Boiling Point: 407.7 °C at 760 mmHg
• Flash Point: 200.4 °C
• Density: 1.39 g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 209.0243562
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=C1Cl)C(=O)O

Technology Process of 1H-Indole-3-carboxylic acid, 2-chloro-1-methyl-

There total 4 articles about 1H-Indole-3-carboxylic acid, 2-chloro-1-methyl- 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: 78.0%

2-chloro-1-methyl-1H-indole-3-carboxaldehyde (24279-74-1) → 2-chloro-1-methyl-1H-indole-3-carboxylic acid (54778-21-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In 1,4-dioxane; for 6.5h;

DOI:10.1021/jm960689b

Reference yield:

2-chloroindole-3-carboxaldehyde (5059-30-3) → 2-chloro-1-methyl-1H-indole-3-carboxylic acid (54778-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / K₂CO₃ / acetone / 16 h

2: 78 percent / 2-methyl-2-butene, aq. NaClO₂, NaH₂PO₄ / dioxane / 6.5 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium carbonate; In 1,4-dioxane; acetone;

DOI:10.1021/jm960689b

Reference yield:

N-methyl-2-indolinone (61-70-1) → 2-chloro-1-methyl-1H-indole-3-carboxylic acid (54778-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) POCl₃ / 1.) CH₂Cl₂, 25 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 38 h

2: 78 percent / 2-methyl-2-butene, aq. NaClO₂, NaH₂PO₄ / dioxane / 6.5 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trichlorophosphate; In 1,4-dioxane;

DOI:10.1021/jm960689b

upstream raw materials:

2-chloro-1-methyl-1H-indole-3-carboxaldehyde

N-methyl-2-indolinone

2-chloroindole-3-carboxaldehyde

Downstream raw materials:

2-chloro-N-<<(4-methoxycarbonyl)phenyl>methyl>-1-methyl-1H-indole-3-carboxamide

1-(2-Chloro-1-methyl-1H-indole-3-carbonyl)-3-(4-chloro-phenyl)-urea

2-chloro-1-methyl-1H-indole-3-carbonyl chloride

Refernces

• 1、 Kutschy, Peter,Suchy, Mojmír,Andreani, Aldo,Dzurilla, Milan,Rossi, Maddalena. "A new photocyclization approach to the rare 1,3-thiazino[6,5-b]indol-4-one derivatives". . p. 9281 - 9283. Retrieved 2007/10/03.