1825-31-6

Usage

Uses

Used in Pesticide and Insecticide Applications:
1,4-Dichloronaphthalene is used as a pesticide and insecticide due to its effectiveness in controlling and eliminating pests. Its strong chemical properties make it a potent agent against various insects and pests that can damage crops and stored products.
Used in Fumigant Applications for Stored Grains:
In the agricultural industry, 1,4-Dichloronaphthalene is used as a fumigant for stored grains to protect them from infestation by insects and other pests. Its ability to penetrate and eliminate pests within stored grain products makes it a valuable tool in maintaining the quality and safety of food supplies.

InChI:InChI=1/C10H6Cl2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

Upstream product

• 91-20-3 naphthalene 
• 605-61-8 1-chloro-4-nitronaphthalene 
• 605-62-9 4-nitro-1-naphthol 
• 605-36-7 1,2,3,4-tetrahydro-1,2,3,4-tetrachloronaphthalene 
• 6328-72-9 4-chloro-1-naphthylsulphonic acid 
• 67-56-1 methanol 
• 605-36-7 naphtalene α-tetrachloride 
• 124-41-4 sodium methylate 
• 67-64-1 acetone 
• 605-36-7 (r-1,t-2,c-3,t-4)-1,2,3,4-tetrachlorotetralin 
• 605-36-7 naphtalene δ-tetrachloride 
• 90-13-1 1-Chloronaphthalene 
• 7719-09-7 thionyl chloride 
• 7791-25-5 sulfuryl dichloride 

Downstream Products

• 52043-46-6 4,7-dichloro-3H-isobenzofuran-1-one 
• 16110-99-9 3,6-dichlorophthalic acid 
• 2750-81-4 1,4-dichloro-5-nitro-naphthalene 
• 4684-12-2 1-amino-4-chloronaphthalene 
• 601-70-7 3,3-dichlorophthalide 
• 56961-94-5 5,8-dichloro-1,4-naphthoquinone 

Relevant academic research and scientific papers

Degradation of one-side fully-chlorinated 1,2,3,4-tetrachloronaphthalene over Fe-Al composite oxides and its hypothesized reaction mechanism

The degradation of 1,2,3,4-tetrachloronaphthalene (CN-27) featuring a one-side fully-chlorinated aromatic ring, was evaluated over three of the prepared rod-like Fe-Al composite oxides (FeAl-1, FeAl-5 and FeAl-10). The results showed that their reactive activities were in the order of FeAl-5 ≈ FeAl-10 ? FeAl-1, which could be attributed to their different pore structural properties and reactive sites caused by the different phase interaction between iron species and the γ-Al2O3. The generation of trichloronaphthalenes (1,2,3-TrCN and 1,2,4-TrCN, i.e. CN-13 and CN-14), dichloronaphthalenes (1,2-DiCN, 1,3-DiCN, 1,4-DiCN and 2,3-DiCN, i.e. CN-3, CN-4, CN-5 and CN-10) and monochloronaphthalenes (1-MoCN and 2-MoCN, i.e. CN-1 and CN-2) suggested the occurrence of successive hydrodechlorination reactions. The amount of CN-14 exceeded that of CN-13 from 71.5% to 77.7% across the three different systems, revealing the preferred occurrence of the first hydrodechlorination step at the β-position. This is dissimilar to the preference at the α-position observed during the dechlorination of octachloronaphthalene (CN-75) over micro/nano Fe3O4. The structural differences between one-side and two-side fully-chlorinated aromatic rings would have a pronounced impact on the reactivity of the chlorine substitution position. The major hydrodechlorination pathway was judged to be CN-27 → CN-14 → CN-4 → CN-2. Additionally, the detected 1,2,3,4,6-pentachloronaphthalene (CN-50) and 1,2,4,6/7-tetrachloronaphthalenes (CN-33/34) suggested the reverse chlorination reaction also happened while the hydrodechlorination reaction was occurring. The C-Cl bond dissociation energies (BDEs) of the parent and daughter polychlorinated naphthalene (PCN) congener were calculated using density functional theory (DFT), to achieve a deeper understanding of a different product yield distribution.

Solid-state reaction of a lead tetraacetate - Metal halide system with naphthalene under mechanical activation

A mechanically activated solid-state reaction of halogenation of naphthalene with a Pb(OAc)4 - alkaline or alkaline-earth metal halide system was carried out to yield 1-halonaphthalene as the main reaction product and 1,4-dihalonaphthalene. The solid-state halogenation of naphthalene is more selective than a liquid-phase reaction.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides

The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in

Mild chlorination of aromatic compounds with tin(IV) chloride and lead tetraacetate

SnCl4/Pb(OAc)4 acts as a safe source of Cl2 for the chlorination of aromatic compounds. A variety of aromatic compounds are effectively chlorinated with SnCl4/Pb(OAc)4 under mild conditions. The mixture is a selective chlorinating agent, particularly with polyalkylbenzenes, polycyclic aromatic compounds and anisoles.