4-Chloro-1,2-naphthalenedione

Base Information

• Chemical Name: 4-Chloro-1,2-naphthalenedione
• CAS No.: 6655-90-9
• Molecular Formula: C10H5ClO2
• Molecular Weight: 192.601
• Hs Code.: 2914700090
• Mol file: 6655-90-9.mol

Synonyms:1,2-Naphthoquinone,4-chloro- (6CI,8CI);4-Chloro-o-naphthoquinone;

Chemical Property of 4-Chloro-1,2-naphthalenedione

Chemical Property:

• Vapor Pressure: 0.000326mmHg at 25°C
• Refractive Index: 1.625
• Boiling Point: 320.1 °C at 760 mmHg
• Flash Point: 134.7 °C
• PSA: 34.14000
• Density: 1.42 g/cm³
• LogP: 2.03170
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

4-Chloronaphthalene-1,2-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Chloro-1,2-naphthalenedione

There total 9 articles about 4-Chloro-1,2-naphthalenedione 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: 85.0%

4-chloronaphthalen-1-ol (604-44-4) → 4-chloronaphthalene-1,2-dione (6655-90-9)

Guidance literature:

With tert.-butylhydroperoxide; 3 A molecular sieve; titanium(IV) isopropylate; In dichloromethane; for 20h;

DOI:10.1055/s-1990-27116

Reference yield: 63.0%

2,4-dichloronaphthol (2050-76-2) → 2-chloro-1,4-naphthoquinone (1010-60-2) + 4-chloronaphthalene-1,2-dione (6655-90-9)

Guidance literature:

With lead(IV) acetate; In benzene; for 10h; Ambient temperature;

DOI:10.1055/s-1980-29284

Reference yield: 5.0%

1-Chloronaphthalene (90-13-1) → 5-chloronaphthalene-1,4-dione (40242-15-7) + 4-chloronaphthalene-1,2-dione (6655-90-9)

Guidance literature:

With dihydrogen peroxide; acetic acid; In water; at 40 ℃; for 24h;

DOI:10.1002/ejoc.202100861

upstream raw materials:

4-chloronaphthalen-1-ol

2,4-dichloronaphthol

1,4-dichloro-[2]naphthol

1-Chloronaphthalene

Downstream raw materials:

2,3-dimethyl-phenanthrene-9,10-dione

4-nitro-benzoic acid-(4-chloro-1-hydroxy-[2]naphthyl ester)

4-(4-oxo-2-buten-1-ylidene)-2-hydroxynaphthalen-1(4H)-one

4-chloro-3',4'-dihydro-5'-methylspiro-1,4'-dione

Refernces

• 1、 Pancrazzi, Francesco,Maestri, Giovanni,Maggi, Raimondo,Viscardi, Rosanna. "Oxidative Dearomatization of Phenols and Polycyclic Aromatics with Hydrogen Peroxide Triggered by Heterogeneous Sulfonic Acids". supporting information. p. 5407 - 5414. Retrieved 2021/10/25.
• 2、 Krohn,Rieger,Bruggmann. "Transition metal catalyzed oxidations; 4. Improved method for the oxidation of 1- and 2-naphthols to 1,2-naphthoquinones". . p. 1141 - 1143. Retrieved 2007/10/02.