161811-59-2

Basic information

• Product Name: 2-bromo-8-hydroxy-6-methylnaphthalene-1,4-dione
• Synonyms: 2-bromo-8-hydroxy-6-methyl-1,4-naphthoquinone; 2-Bromo-8-hydroxy-6-methylnaphthoquinone
• CAS NO: 161811-59-2
• Molecular Formula: C₁₁H₇BrO₃
• Molecular Weight: 267.0755
• Mol File: 161811-59-2.mol

Chemical Properties

• Boiling Point: 443.6°C at 760 mmHg
• Flash Point: 222.1°C
• Density: 1.785g/cm³
• Vapor Pressure: 1.75E-08mmHg at 25°C
• Refractive Index: 1.693
• CAS DataBase Reference: 2-bromo-8-hydroxy-6-methylnaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-8-hydroxy-6-methylnaphthalene-1,4-dione(161811-59-2)
• EPA Substance Registry System: 2-bromo-8-hydroxy-6-methylnaphthalene-1,4-dione(161811-59-2)

Safety Data

• Hazardous Substances Data: 161811-59-2(Hazardous Substances Data)

Upstream product

• 120016-59-3 3-(hydroxymethyl)-5,8-dimethoxynaphthalen-1-ol 
• 101459-25-0 2-bromo-5,8-dimethoxy-3-methylnaphthalen-1-ol 
• 25932-95-0 Ethyl 4-(acetyloxy)-5,8-dimethoxy-2-naphthalenecarboxylate 
• 14787-38-3 7-methyljuglone 
• 50559-08-5 5,8-dimethoxy-3-methylnaphthalen-1-ol 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 76915-33-8 (Z)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane 
• 73311-51-0 1-methoxy-3-methyl-1-trimethylsilyloxy-1,3-butadiene 

Downstream Products

• 1227181-33-0 11-benzyloxy-1,9-dimethyl-6H-naphtho[2',3':4,5]furo[3,2-c]chromene-6,7,12-trione 
• 1309048-59-6 11-benzyloxy-4,9-dimethyl-6H-naphtho[2',3':4,5]furo[3,2-c]chromene-6,7,12-trione 
• 1227181-32-9 2-bromo-8-benzyloxy-6-methyl-1,4-naphthoquinone 

Relevant articles and documents

Total Synthesis of the Antitumor-Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer

The 2,6′-bijuglone natural product diospyrin and its unnatural 3,6′-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methylju

Synthesis of the reported structure of crassiflorone, a naturally occurring quinone isolated from the African ebony Diospyros crassiflora, and regioisomeric pentacyclic furocoumarin naphthoquinones

A synthesis of the structure reported for the natural product crassiflorone, a furocoumarin naphthoquinone, is described. The key steps are a Diels-Alder reaction to form 2-bromo-8-hydroxy-6-methylnaphthoquinone, followed by O-protection and copper(ii) mediated coupling to 4-hydroxy-5-methylcoumarin to establish the pentacyclic framework whose structure was unambiguously confirmed by X-ray crystallography. Since the spectroscopic data of the synthetic material did not match those reported for the natural product, three further regioisomeric furocoumarin naphthoquinones were prepared by copper(ii) mediated coupling of 4-hydroxy-5- or 8-methyl coumarins with 5-benzyloxy-2-bromo-7-methyl- or 8-benzyloxy-2-bromo-6-methyl-1,4- naphthoquinone. Again the spectroscopic data did not match those of the natural material and therefore the true structure of crassiflorone remains unknown.

Synthesis of the reported structure of crassiflorone, a pentacyclic naphthoquinone isolated from the African ebony diospyros crassiflora

A short synthesis of the furocoumarin naphthoquinone structure reported for the natural product crassiflorone is described, in which the key steps are a Diels-Alder reaction to form 2-bromo-8-hydroxy-6-methylnaphthoquinone, followed by O-protection and co

A convergent total synthesis of the michellamines

A convergent total synthesis of the anti-HIV michellamines (1) is described. The tetraaryl skeleton of the michellamines was constructed by formation first of the inner (nonstereogenic) biaryl axis and subsequently of the two other (stereogenic) axes in a highly convergent manner. The key transformation features a double Suzuki-type cross-coupling reaction between binapthalene ditriflate 26 and isoquinolineboronic acid 35. Ditriflate 26 is synthesized in six steps starting from diene 6 and 2,6-dibromobenzoquinone (9) in 21% overall yield. For large scale production of 26, a substantially shortened version of an existing procedure for the preparation of bisnaphthoquinone 13 was also developed, which allows for the preparation of 13 from benzoquinone and diene 6 in five steps and 67% overall yield. Binaphthoquinone 13 was subsequently converted into ditriflate 26 in three steps and 67% overall yield. By the described synthetic strategy, michellamines A (1a) and B (1b) are produced (1a:1b = 1:2.5) in 24.6% overall yield from diene 6. Curiously, none of the nonnaturally occurring atropoisoner 1c is formed.

Convergent total synthesis of the michellamines

The total synthesis of both michellamine A (1a) and B (1b), by consecutive construction first of the inner (non-stereogenic) axis and subsequently the two outer (stereogenic) axes in a highly convergent manner, is described. The michellamines are of consi