4-Chloro-6-methoxyindole

Base Information

• Chemical Name: 4-Chloro-6-methoxyindole
• CAS No.: 93490-31-4
• Molecular Formula: C₉H₈ClNO
• Molecular Weight: 181.622
• Hs Code.: 2933990090
• UNII: 62M589BM1E
• DSSTox Substance ID: DTXSID00239439
• Nikkaji Number: J527.859G
• Wikidata: Q27263498
• Mol file: 93490-31-4.mol

Synonyms:4-chloro-6-methoxyindole

Chemical Property of 4-Chloro-6-methoxyindole

Chemical Property:

• Appearance/Colour: Brown Solid
• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: 1.647
• Boiling Point: 333.9 °C at 760 mmHg
• Flash Point: 155.7 °C
• PSA: 25.02000
• Density: 1.317 g/cm³
• LogP: 2.82990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 181.0294416
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-6-methoxy Indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN2)C(=C1)Cl

Technology Process of 4-Chloro-6-methoxyindole

There total 8 articles about 4-Chloro-6-methoxyindole 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:

2-nitro-4-fluorotoluene (446-10-6) → 4-chlor-6-methoxyindol (93490-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 45 percent / fuming nitric acid, fuming sulfuric acid / 6 h / 80 - 90 °C

2: 57 percent / sodium / 2 h / Heating

3: 35 percent / sodium bicarbonate, sodium sulfide nonahydrate / H₂O / 1 h / Heating

4: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H₂O / 0 - 5 °C / 2.) 10 min

5: 1.) pyrrolydine; 2.) H₂ / 2.) 5percent palladium on charcoal / 1.) DMF, reflux, 3 h; 2.) 4 atm

With pyrrolidine; hydrogenchloride; sodium sulfide; sulfuric acid; hydrogen; nitric acid; sodium; sodium hydrogencarbonate; copper(l) chloride; sodium nitrite; palladium on activated charcoal; In water;

DOI:10.1021/ja00274a043

Reference yield:

2-amino-4-methoxy-6-nitrotoluene (16024-30-9) → 4-chlor-6-methoxyindol (93490-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H₂O / 0 - 5 °C / 2.) 10 min

2: 1.) pyrrolydine; 2.) H₂ / 2.) 5percent palladium on charcoal / 1.) DMF, reflux, 3 h; 2.) 4 atm

With pyrrolidine; hydrogenchloride; hydrogen; copper(l) chloride; sodium nitrite; palladium on activated charcoal; In water;

DOI:10.1021/ja00274a043

Reference yield:

2,6-dinitro-4-methoxytoluene (16024-29-6) → 4-chlor-6-methoxyindol (93490-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / sodium bicarbonate, sodium sulfide nonahydrate / H₂O / 1 h / Heating

2: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H₂O / 0 - 5 °C / 2.) 10 min

3: 1.) pyrrolydine; 2.) H₂ / 2.) 5percent palladium on charcoal / 1.) DMF, reflux, 3 h; 2.) 4 atm

With pyrrolidine; hydrogenchloride; sodium sulfide; hydrogen; sodium hydrogencarbonate; copper(l) chloride; sodium nitrite; palladium on activated charcoal; In water;

DOI:10.1021/ja00274a043

upstream raw materials:

vinyl acetate

N-(3-chloro-5-methoxyphenyl)acetohydroxamsaeure

N,N-dimethyl-formamide dimethyl acetal

2-chloro-4-methoxy-6-nitrotoluene

Downstream raw materials:

4-Chloro-2-hydroxy-6-methoxy-1-nitroso-1,2-dihydro-indol-3-one oxime

Refernces

• 1、 Buechi, George,Lee, Gary C. M.,Yang, David,Tannenbaum, Steven R.. "Direct Acting, Highly Mutagenic, α-Hydroxy N-Nitrosamines from 4-Chloroindoles". . p. 4115 - 4119. Retrieved 2007/10/02.