14209-08-6

Usage

Family

Dihalo-substituted polycyclic aromatic hydrocarbons (PAHs)

Known properties

Potential toxic and carcinogenic properties

Usage

Often used as a precursor in the synthesis of various organic compounds and materials

Structure

Napthalene ring system with two bromine atoms attached to adjacent carbon atoms in the ring

Health and environmental risks

May pose various health and environmental risks due to its potential toxicity and persistence in the environment

Handling and disposal

Should be handled and disposed of with caution and in accordance with safety regulations

Upstream product

• 106552-18-5 Z-1,2-dibromo-1,2-dihydroacenaphthylene 
• 25226-58-8 trans-1,2-dibromo-1,2-dihydroacenaphthylene 
• 83-32-9 acenaphthene 
• 208-96-8 acenaphthylene 
• 51392-61-1 1-bromo-1H,3H-naphtho<1,8-cd>thiopyran 2,2-dioxide 
• 29376-61-2 1H,3H-Naphtho<1,8-cd>thiopyran 2,2-Dioxide 
• 203-85-0 1H,3H-naphtho<1,8-cd>thiopyran 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 2026-08-6 naphthalene-1,8-diyldimethanol 

Downstream Products

• 208-96-8 acenaphthylene 
• 477-77-0 1,1'-biacenaphthylenyliden-2-one 
• 2235-15-6 1(2H)-acenaphthylenone 
• 83-32-9 acenaphthene 
• 129286-41-5 (6bS,7S,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylene-7-carboxylic acid ethyl ester 
• 129286-41-5 (6bS,7R,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylene-7-carboxylic acid ethyl ester 
• 129286-42-6 [(6bS,7R,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylen-7-yl]-methanol 
• 129286-42-6 [(6bS,7S,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylen-7-yl]-methanol 
• 129286-44-8 (6bS,7R,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylene-7-carbaldehyde 
• 129286-44-8 (6bS,7S,7aR)-6b-(4-Fluoro-phenyl)-7,7a-dihydro-6bH-cyclopropa[a]acenaphthylene-7-carbaldehyde 
• 129286-43-7 ethyl <2-(4'fluorophenyl)acenaphtylen-1-yl>acetate 
• 129286-40-4 1-(4-fluorophenyl)acenaphthylene 
• 54736-49-1 1-bromoacenaphthylene 
• 10035-10-6 hydrogen bromide 

Relevant academic research and scientific papers

Design, synthesis and characterization of a modular bridging ligand platform for bio-inspired hydrogen production

Synthesis and characterization of a novel type of ambident bridging ligands joining together the functional prerequisites for visible-light absorption, photoinduced electron transfer and catalytic proton reduction is presented. This class of compounds consists of a chromophoric 1,2-diimine-based π-acceptor site and a rigid polyaromatic dithiolate chelator. Due to the presence of a common conjugated linker moiety with an intrinsic two-electron redox reactivity and a suitable orbital coupling of the subunits, a favourable situation for vectorial multielectron transfer from attached electron donors to a catalytic acceptor site is provided. As an example for the application of this kind of bifunctional ligand systems, a [FeFe]-hydrogenase enzyme model compound is prepared and structurally characterized. Electrocatalytic hydrogen formation with this complex is demonstrated.

Ramberg-Baecklund Reaction of 1,3-Dibromo-1H,3H-naphthothiopyran 2,2-Dioxide. Formation of Acenaphthyne Intermediate

Radical bromination of 1H,3H-naphthothiopyran 2,2-dioxide (15) gave the corresponding monobromo sulfone 16 (48percent), dibromo sulfone 12 (43percent; cis/trans = 64/36), and tribromo sulfone 17 (5percent).Ramberg-Baecklund reaction of 12 was investigated under a variety of coditions with expectation of the formation of thiirene dioxide 11 from which generation of acenaphthyne (5) would be expected both thermally and photochemically.Observed characteristic features of the reaction are as follows: (i) the use of triethylamine as base yielded 1-bromo-acenaphthylene (20; 39percent) and debrominated products 15 (5percent) and 16 (9percent); (ii) the use of sodium methoxide as base afforded decacyclene (3) surprisingly, though in a trace amount, in addition to 20 (75percent) and acenaphthylene (18; 9percent); (iii) the use of potassium tert-butoxide as base gave an improved yield of 3 (5percent) along with 20 (36percent) and 18 (27percent).The formation of 3 may best be rationalized by assuming the generation of acenaphthyne intermediate 5 from 11 by loss of sulfur dioxide.

Oxidation by DMSO. II. An efficient synthesis of α,β-diketones from α,β-dibromides

α,β-Dibromides refluxed in DMSO are oxidised into α,β-diketones. The reaction takes place rapidly under microwave irradiation.

Solid-State Organic Reactions Proceeding by Pulverization of Inorganic Solid-Supports. Reactions of Iodosobenzene with Unsaturated Hydrocarbons on Acid-Treated Silica Gel

Pulverization of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene, and alkenes or an alkyne in the absence of a solvent brings about smooth and rapid reaction to give halogenated or oxidized products in good yields.

1,2-DERIVATIVES OF ACENAPHTHYLENE. IX. NEW DATA ON ADDITION OF HALOGENS TO ACENAPHTHYLENE

Acenaphthylene adds molecular halogens nonstereospecifically.The relative amount of the Z-dihalide increases with decrease in the polarity of the solvent.Z-1,2-dibromo-1,2-dihydroacenaphthylene is not changed after a year at 4-6 deg C; the best solvent for its production is hexane.