2198-75-6

Basic information

• Product Name: 1,3-dichloronaphthalene
• Synonyms: 1,3-dichloronaphthalene;2,4-Dichloronaphthalene
• CAS NO: 2198-75-6
• Molecular Formula: C₁₀H₆Cl₂
• Molecular Weight: 197.06064
• EINECS: 218-603-4
• Mol File: 2198-75-6.mol

Chemical Properties

• Melting Point: 62.3°C
• Boiling Point: 302.76°C (rough estimate)
• Flash Point: 139.5°C
• Appearance: /
• Density: 1.3147 (estimate)
• Vapor Pressure: 0.00266mmHg at 25°C
• Refractive Index: 1.5974 (estimate)
• CAS DataBase Reference: 1,3-dichloronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dichloronaphthalene(2198-75-6)
• EPA Substance Registry System: 1,3-dichloronaphthalene(2198-75-6)

Safety Data

• Hazardous Substances Data: 2198-75-6(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
1,3-dichloronaphthalene is used as an active ingredient in pesticides for its insecticidal properties, helping to control and eliminate pests that can damage crops and spread diseases.
Used in Insect Repellent Applications:
As an insect repellent, 1,3-dichloronaphthalene is employed to deter insects, reducing the risk of insect-borne illnesses and protecting both humans and animals from bites.
Used in Dye Production:
In the dye industry, 1,3-dichloronaphthalene is utilized in the manufacturing process of various dyes, contributing to the colorfastness and quality of the final product.
Used as a Moth Repellent in Household Products:
1,3-dichloronaphthalene is used as a moth repellent in the form of mothballs, protecting fabrics and garments from damage caused by moth larvae.

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

Upstream product

• 29242-87-3 1-amino-2,4-dichloronaphthalene 
• 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 
• 605-36-7 1,2,3,4-tetrahydro-1,2,3,4-tetrachloronaphthalene 
• 10026-13-8 phosphorus pentachloride 
• 6357-85-3 2-naphthol-4-sulfonic acid 
• 54393-68-9 naphthalene-1,3-disulfonyl chloride 
• 7647-01-0 hydrogenchloride 
• 794528-88-4 N(2,4-dichloro-[1]naphthyl)-acetamide 
• 20020-02-4 1,2,3,4-tetrachloronaphthalene 

Downstream Products

• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

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.

PROCESS FOR SYNTHESIS OF AROMATIC COMPOUNDS

The present invention refers to a process for preparing a compound of the formula (I) wherein R denotes an organic radical which, together with the two carbon atoms to which it is bonded, forms a carbocyclic or heterocyclic ring; R1, R2, R3 and X, independently, denote hydrogen, halogen, nitro, cyano or an organic radical; or R1 and R2 or R2 and R3, together with the carbon atoms to which they are bonded, form a ring; which comprises exposing a compound of the formula (II) wherein R1, R2, R3 and X are defined as given above and Y and Z, independently, have one of the meanings of X; to an energy source in the presence of a catalyst system.

A remarkably simple and efficient benzannulation reaction

(Chemical Equation Presented) On a short fuse: Although fused aromatic rings are common structural motifs in natural products, there are relatively few direct methods for the preparation of such systems from acyclic precursors. An atom-transfer radical cyclization carried out under microwave (MW) irradiation has now been developed which gives rapid access to functionalized aromatic compounds from readily available starting materials (see scheme).