2-Chloro-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Chloro-1,4-naphthoquinone
• CAS No.: 1010-60-2
• Molecular Formula: C10H5ClO2
• Molecular Weight: 192.601
• Hs Code.: 2914700090
• European Community (EC) Number: 213-776-2
• NSC Number: 400597
• UNII: FOF3PSJ59Z
• DSSTox Substance ID: DTXSID00143623
• Nikkaji Number: J20.958I
• Wikidata: Q27103536
• Metabolomics Workbench ID: 51603
• ChEMBL ID: CHEMBL349147
• Mol file: 1010-60-2.mol

Synonyms:2-chloro-1,4-naphthoquinone;chloro-K3

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

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 0.000701mmHg at 25°C
• Melting Point: 108-109°C
• Refractive Index: 1.625
• Boiling Point: 308 °C at 760 mmHg
• Flash Point: 129.3 °C
• PSA: 34.14000
• Density: 1.42 g/cm³
• LogP: 2.18830
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 191.9978071
• Heavy Atom Count: 13
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-1- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C=C(C2=O)Cl
• Uses: A substituted naphthoquinones as insecticides and acaricides.

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

There total 41 articles about 2-Chloro-1,4-naphthoquinone 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: 100.0%

[1,4]naphthoquinone (130-15-4) → 2-chloro-1,4-naphthoquinone (1010-60-2)

Guidance literature:

With chlorine; mercury(II) oxide; In tetrachloromethane; for 0.5h;

DOI:10.1080/00397919408011701

Reference yield: 100.0%

2-hydroxynaphtho-1,4-quinone (83-72-7) → 2-chloro-1,4-naphthoquinone (1010-60-2)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1055/s-2007-986652

Reference yield: 77.9%

1-acetoxy-1,3-butadiene (1515-76-0) + chloro-p-hydroquinone (615-67-8) → 2-chloro-1,4-naphthoquinone (1010-60-2)

Guidance literature:

With oxygen; In dimethyl sulfoxide; at 55 ℃; for 24h; pH=4.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/cplu.201300066

upstream raw materials:

1-hydroxy-2,4-dinitronaphthalene

2,4-dichloronaphthalene

1,4-dihydroxy-2-naphthoic acid

2-chloro-5,8-dihydro-naphthalene-1,4-diol

Downstream raw materials:

deoxylapachol

2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione

2-chloro-2,3-dihydro-3,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone

2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Refernces

• 1、 Thapliyal,Singh,Khanna. "Chlorination of quinonoid compounds using dichlorine monoxide". . p. 1079 - 1083. Retrieved 1994.
• 2、 Perumal,Bhatt. "". . p. 3099. Retrieved 1979.
• 3、 Thapliyal, Prakash Chander. "Iodine catalyzed chlorination of naphthoquinones using metal (II) chlorides". . p. 1123 - 1126. Retrieved 1998.
• 4、 Best, Wayne M.,Sims, Colette G.,Winslade, Merilyn. "Palladium-Catalysed Cross Coupling of Arylboronic Acids with 2-Chloro-1,4-naphthoquinones: The Synthesis of 2-Aryl- and 2,3-Bisaryl-1,4-naphthoquinones". . p. 401 - 404. Retrieved 2001.
• 5、 Boisvert, Louise,Brassard, Paul. "Regiospecific Addition of Monooxygenated Dienes to Halo Quinones". . p. 4052 - 4059. Retrieved 1988.
• 6、 Calil, Felipe A.,David, Juliana S.,Chiappetta, Estela R.C.,Fumagalli, Fernando,Mello, Rodrigo B.,Leite, Franco H.A.,Castilho, Marcelo S.,Emery, Flavio S.,Nonato, M.Cristina. "Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase". . p. 357 - 366. Retrieved 2019/02/19.