67922-26-3

Basic information

• Product Name: 1,2,3,4,6-PENTACHLORONAPHTHALENE
• Synonyms: 1,2,3,4,6- pentachloro
• CAS NO: 67922-26-3
• Molecular Formula: C₁₀H₃Cl₅
• Molecular Weight: 300.3958
• Mol File: 67922-26-3.mol

Chemical Properties

• Boiling Point: 373.7°Cat760mmHg
• Flash Point: 186.6°C
• Appearance: /
• Density: 1.638g/cm³
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 1,2,3,4,6-PENTACHLORONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-PENTACHLORONAPHTHALENE(67922-26-3)
• EPA Substance Registry System: 1,2,3,4,6-PENTACHLORONAPHTHALENE(67922-26-3)

Safety Data

• Hazardous Substances Data: 67922-26-3(Hazardous Substances Data)

Usage

Classification

Polychlorinated naphthalene (PCN)

Convention

Stockholm Convention on Persistent Organic Pollutants

Physical State

White to off-white crystalline solid

Odor

Strong

Solubility

Not easily soluble in water

Uses

Primarily used as a fungicide and insecticide

Production and Use

Heavily restricted due to toxicity and environmental persistence

Environmental Impact

Bioaccumulates in organisms

Health Effects

Potential carcinogen, reproductive and developmental toxicity

InChI:InChI=1/C10H3Cl5/c11-4-1-2-5-6(3-4)8(13)10(15)9(14)7(5)12/h1-3H

Upstream product

• 58877-88-6 1,2,3,4,6,7-hexachloronaphthalene 
• 20020-02-4 1,2,3,4-tetrachloronaphthalene 

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.

Selective reduction of polychlorinated naphthalenes with zinc

Reduction of polychlorinated naphthalenes with zinc in acetic acid requires the presence of three chlorine atoms in positions 1, 2, and 8, the chlorine atom in position 1 being reduced. The relative rates of reduction of various polychloronaphthalenes were measured.