17135-74-9

Basic information

• Product Name: 1,8-DIBROMONAPHTALENE
• Synonyms: 1,8-DIBROMONAPHTALENE;1,8-dibroMonaphthalene 1,8-DBN;1,8-dibroMophthalene;1,8-DBN;Naphthalene,1,8-dibromo-
• CAS NO: 17135-74-9
• Molecular Formula: C₁₀H₆Br₂
• Molecular Weight: 285.96
• Product Categories: OLED materials,pharm chemical,electronic;Dibromonaphthalene
• Mol File: 17135-74-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 108.0 to 112.0 °C
• Boiling Point: 140°C/0.1mmHg(lit.)
• Flash Point: 184.7 °C
• Appearance: off-white solid
• Density: 1.834 g/cm³
• Vapor Pressure: 0.000184mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• Solubility: soluble in Toluene
• CAS DataBase Reference: 1,8-DIBROMONAPHTALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-DIBROMONAPHTALENE(17135-74-9)
• EPA Substance Registry System: 1,8-DIBROMONAPHTALENE(17135-74-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 17135-74-9(Hazardous Substances Data)

Usage

Description

1,8-Dibromonaphtalene is a chemical compound with the molecular formula C10H6Br2. It is a naphthalene derivative in which the 1 and 8 positions of the naphthalene structure are substituted by bromine atoms. Its chemical properties are characterized by its aromatic nature and the presence of two bromine substituents, which make it effective in various chemical reactions, particularly ones involving substitutions or coupling.

Uses

Used in Organic Chemistry Research:
1,8-Dibromonaphtalene is used as a research compound for its high reactivity and ability to act as a precursor for other compounds. It is particularly valuable in the synthesis of various organic molecules, where its bromine substituents can be replaced or coupled with other functional groups.
Used in Chemical Synthesis:
1,8-Dibromonaphtalene is used as a synthetic intermediate for the production of other chemical compounds. Its reactivity and bromine substituents make it a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Material Science:
1,8-Dibromonaphtalene is used as a component in the development of new materials, such as polymers and coatings, where its chemical properties can contribute to desired characteristics like stability, reactivity, or solubility.
Note: It is important to handle 1,8-Dibromonaphtalene with care, as it may pose health risks due to its brominated nature. Proper safety measures should be taken during its use in research and industrial applications.

InChI:InChI=1/C10H6Br2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H

Upstream product

• 479-27-6 naphthalene-1,8-diamine 
• 2112-99-4 3-amino-4H-naphtho<1,8-de>triazine 
• 204-03-5 1H-naphtho[1,8-de][1,2,3]triazine 
• 1729-99-3 8-bromonaphthalene-1-carboxylic acid 
• 1730-04-7 1,8-diiodonaphthalene 
• 518-05-8 Naphthalene-1,8-dicarboxylic acid 
• 506-68-3 bromocyane 
• 61767-59-7 (naphthalene-1,8-diyl)dilithium 

Downstream Products

• 141397-24-2 1-bromo-8-(2-methylphenyl)naphthalene 
• 96773-95-4 1,8-bis(diphenylhydroxymethyl)naphthalene 
• 947617-22-3 naphthalene-1,8-diboronic acid 
• 91-20-3 naphthalene 
• 119-64-2 tetralin 
• 91-17-8 decalin 
• 783333-49-3 anti-1,8-bis(3,3'-(3,5-dimethylphenyl)-9,9'-diacridyl)naphthalene 
• 92-52-4 biphenyl 
• 605-02-7 1-phenylnaphthalene 
• 1038-67-1 1,8-diphenylnaphthalene 
• 673458-28-1 1,8-bis[bis(p-methoxyphenyl)hydroxymethyl]naphthalene 

Relevant articles and documents

Facile Route to Quadruply Annulated Borepins

A two-step synthesis sequence furnishes quadruply annulated borepins in high yields. The first step involves a nucleophilic substitution reaction between aryl-BF3K salts (aryl = mesityl, phenyl) and lithiated bromonapthalene derivatives LiNaphBr,R (HNaphBr,R = 8-bromonaphthalene (a), 5-bromoacenaphthene (b), 5-bromoacenaphthylene (c)). In the second step, the resulting heteroleptic triarylboranes aryl-B(NaphBr,R)2 (3a-c) are subjected to an intramolecular Ni-mediated Yamamoto reaction to close the seven-membered rings and create the borepins 4a-c. Only in the case of 3b is the Yamamoto reaction accompanied by a C-H activation reaction furnishing the 7-hydro-7-borabenzo[de]anthracene derivative 5. The product ratio 4b/5 can be influenced by control of the local Ni(0) concentration. The borepins 4a-c are benchtop stable and highly soluble even in hexane. Compounds 4a-c undergo reversible one-electron reduction; 4c is also able to accept a second electron in a reversible manner and already at moderate potential values (E1/2 = ?1.49 V and ?1.84 V (vs FcH/FcH+)). 4a, 4b, and 5 show photoluminescence in the blue-green region of the spectrum, while 4c is nonfluorescent, which is likely attributable to an intramolecular charge-transfer transition.

Synthesis of 1,2-disubstituted acenaphthylenes by palladium-catalyzed annulation reactions of dibromoarenes with internal alkynes

A simple and versatile route to 1,2-disubstituted acenaphthylenes has been developed. The method involves palladium-catalyzed annulation of 1,8-dibromonaphthalene or 5,6-dibromoacenaphthylene with an internal alkyne, and does not require any organometallic reagent. A range of 1,2-disubstituted acenaphthylenes and 5,6-disubstituted 1,2-dihydrocyclopenta[f,g]acenaphthylenes were prepared in moderate to good yields. The method provides a rapid and simple route to dibenzo[j,l]fluoranthene through an Ullmann coupling. Georg Thieme Verlag Stuttgart New York.