51595-06-3

Basic information

• Product Name: 2-tert-butylnaphthalene-1,4-dione
• Synonyms: 1,4-Naphthalenedione, 2-(1,1-dimethylethyl)-
• CAS NO: 51595-06-3
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.2598
• Mol File: 51595-06-3.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 330.1°C at 760 mmHg
• Flash Point: 123.7°C
• Density: 1.147g/cm³
• Vapor Pressure: 0.00017mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 2-tert-butylnaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-butylnaphthalene-1,4-dione(51595-06-3)
• EPA Substance Registry System: 2-tert-butylnaphthalene-1,4-dione(51595-06-3)

Safety Data

• Hazardous Substances Data: 51595-06-3(Hazardous Substances Data)

Upstream product

• 2876-35-9 2-tert-butylnaphthalene 
• 27286-81-3 2-(tert-butyl)-1-naphthol 
• 546-67-8 lead(IV) tetraacetate 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 130-15-4 [1,4]naphthoquinone 
• 38442-51-2 tert-butylmercury chloride 
• 89025-50-3 2,2-dimethylpropionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 75-98-9 Trimethylacetic acid 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 75-65-0 tert-butyl alcohol 
• 90-15-3 α-naphthol 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 4900-63-4 1-methoxy-4-nitronaphthalene 
• 91-20-3 naphthalene 

Relevant articles and documents

Formation of naphthoquinones and anthraquinones by carbonyl-hydroquinone/benzoquinone reactions: A potential route for the origin of 9,10-anthraquinone in tea

The reaction of 2-alkenals (crotonaldehyde and 2-pentenal) with hydroquinones (hydroquinone and tert-butylhydroquinone) and benzoquinones (benzoquinone, methylbenzoquinone, and methoxybenzoquinone) was studied as a potential route for the endogenous formation of naphthoquinones and anthraquinones in foods. Polycyclic quinones were produced at a low water activity, within a wide pH range, and in the presence of air. 9,10-Anthraquinone formation had an activation energy of 46.1 ± 0.1 kJ·mol?1, and a reaction pathway for the formation of the different naphthoquinones and anthraquinones is proposed. These reactions also took place in tea, therefore suggesting that the common tea pollutant 9,10-anthraquinone is also a process-induced contaminant. In fact, when four commercial teas (from a total of eight studied teas) were heated at 60 °C for 72 h, they significantly (p 0.05) increased the amount of this toxicant. Reduction of 9,10-anthraquinone formation in teas is suggested to be carried out by reducing/scavenging its precursors.

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

Radical-Triggered Tandem Cyclization of 1,6-Enynes with H2O: A Way to Access Strained 1 H-Cyclopropa[ b]naph thalene-2,7-diones

A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.