61836-43-9

Basic information

• Product Name: 3,3'-Bijuglone
• Synonyms: 3,3'-Bijuglone;3,3'-Bisjuglone;8,8'-Dihydroxy-2,2'-bi[1,4-naphthoquinone];8,8'-Dihydroxy-2,2'-binaphthalene-1,1',4,4'-tetrone
• CAS NO: 61836-43-9
• Molecular Formula: C20H10O6
• Molecular Weight: 346.2898
• Mol File: 61836-43-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 565.1°Cat760mmHg
• Flash Point: 309.6°C
• Appearance: /
• Density: 1.636g/cm³
• CAS DataBase Reference: 3,3'-Bijuglone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Bijuglone(61836-43-9)
• EPA Substance Registry System: 3,3'-Bijuglone(61836-43-9)

Safety Data

• Hazardous Substances Data: 61836-43-9(Hazardous Substances Data)

Upstream product

• 6312-53-4 juglone 
• 75445-68-0 5-Benzyloxy-naphthalene-1,4-diol 
• 75445-66-8 8-(benzyloxy)-1-hydroxy-4-methoxynaphthalene 
• 75445-61-3 5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione 
• 61836-39-3 4-methoxy-1,8-naphthalenediol 
• 83-56-7 1,5-dihydroxynaphthalene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 3843-55-8 4,8-dimethoxy-1-naphthol 
• 61836-45-1 5,5'-dimethoxy-3,3'-bi-1,4-naphthoquinone 
• 75445-94-2 8,8'-dihydroxy-4,4'-dimethoxy-2,2'-binaphthylidene-1,1'-quinone 

Downstream Products

• 34341-27-0 8,8'-dihydroxy-3,3'-dimethyl[2,2']binaphthalenyl-1,4,1',4'-tetraone 
• 97308-86-6 8-hydroxy-1-methylbenzindazole-4,9-dione 

Relevant articles and documents

Oxidative coupling of methoxynaphthylenediols

The oxidative coupling of a mixture of 1-methoxy-7-methyl-4,5- naphthylenediol and 4-methoxy-7-methyl-1,5-naphthylenediol using lead(IV) oxide gives the symmetrical bisnaphthalene indigos diosindigo A and diosindigo B together with the corresponding unsymmetrical isomer. Oxidation of the first two by nitric acid gives the binaphthyldiquinones mamegakinone and biramentaceone, respectively; the third gives the unsymmetrical diquinone rotundiquinone. Similar oxidations of related naphthylenediols are described.

SnCl4-mediated oxidative reaction for formation of binaphthoquinone and dinaphthofuran frameworks and its application to natural product synthesis

A simple method was developed for the direct synthesis of 2,2′-binaphthoquinones and dinaphtho[1,2-b;2′,1′-d]furans, utilizing an oxidative reaction via electron donor-acceptor complexes of 1-naphthols with SnCl4 in the absence or presence of dioxygen. As an application of this method to natural product synthesis, we describe a facile biomimetic synthesis of several binaphthoquinones, 3,3′-bijuglone, 3,3′-biplumbagin and elliptinone.

Regioselective Syntheses of 3,3'-Bijuglone, Mamegakinone, Dianellinone, cyclo-Trijuglone, Xylospyrin, and Trianellinone by Phenol-Quinone Addition

Regioselective phenol-quinone addition of juglone (1a), 7-methyljuglone (1b), and stypandrone (1c) in pyridine yields the dimers 3,3-bijuglone (5a), mamegakinone (5c), and dianellinone (5e).In acetic acid mainly the cyclo trimers cyclo-trijuglone (12a), xylospyrin (12d), and trianellinone (12g) are obtained.