Octachloronaphthalene(CAS No. 2234-13-1)

Octachloronaphthalene C10Cl8 (cas 2234-13-1) Molecular Structure

2234-13-1 Structure

Identification and Related Records

【Name】
Octachloronaphthalene
【Iupac name】
1,2,3,4,5,6,7,8-octachloronaphthalene
【CAS Registry number】
2234-13-1
【Synonyms】
Perchloronaphthalene
octachloronaphthane
1,2,3,4,5,6,7,8-OCTACHLORONAPHTHALENE
HALOWAX 1051
octachloro-naphthalen
Perna
OCTACHLORONAPHTHALENE
PCN-75
PERCHLORONAPHTHALENE
OCTACHLORONAPHTHALENE, 20MG, NEAT
【EINECS(EC#)】
218-778-7
【Molecular Formula】
C10Cl8 (Products with the same molecular formula)
【Molecular Weight】
403.73
【Inchi】
InChI=1/C10Cl8/c11-3-1-2(5(13)9(17)7(3)15)6(14)10(18)8(16)4(1)12
【InChIKey】
RTNLUFLDZOAXIC-UHFFFAOYSA-N
【Canonical SMILES】
C12=C(C(=C(C(=C1Cl)Cl)Cl)Cl)C(=C(C(=C2Cl)Cl)Cl)Cl
【MOL File】
2234-13-1.mol

Chemical and Physical Properties

【Appearance】
pale yellow solid with an aromatic odor
【Density】
2
【Melting Point】
185℃
【Boiling Point】
440℃
【Vapour】
5.01E-07mmHg at 25°C
【Refractive Index】
1.684
【Flash Point】
-18 °C
【Water】
Insoluble
【Solubilities】
insoluble in water
【Color/Form】
Crystals from cyclohexane
NEEDLES FROM BENZENE & CARBON TETRACHLORIDE
Waxy pale-yellow solid
【Storage temp】
APPROX 4°C
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 275 NM (LOG E= 4.67); 332 NM (LOG E= 3.87); 345 NM (LOG E= 3.79) SHOULDER
Intense mass spectral peaks: 404 m/z (100%), 402 m/z (85%), 406 m/z (61%), 332 m/z (41%)
UV: 2-194 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 52341 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
IR: 447 (Coblentz Society Spectral Collection)
SD: 1117 (Sadtler Research Laboratories Spectral Collection)
SD: 6747 (Sadtler Research Laboratories Spectral Collection)
WI: 1029 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:403.731 [g/mol]
Molecular Formula:C10Cl8
XLogP3-AA:8.2
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:403.744921
MonoIsotopic Mass:399.750822
Topological Polar Surface Area:0
Heavy Atom Count:18
Formal Charge:0
Complexity:254
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R22
【Safety Statements 】
S36/39
【Safety】

Poison by inhalation, ingestion, and skin contact. When heated to decomposition it emits highly toxic fumes of Cl. See also CHLORINATED HYDROCARBONS, AROMATIC.
 

Hazard Codes:Xn,N,F
Xn:HarmfulN:Dangerous for theenvironmentF:Highly Flammable
Risk Statements
R22:Harmful if swallowed.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R38:Irritating to the skin.
R11:Highly Flammable.
Safety Statements
S36/39:Wear suitable protective clothing and eye/face protection .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S60:This material and/or its container must be disposed of as hazardous waste .
RIDADR:UN 1145 3/PG 2
RTECS:QK0250000
Hazardous Substances Data:2234-13-1(Hazardous Substances Data)
 

【Skin, Eye, and Respiratory Irritations】
Toxic by Inhalation and skin contact.
【Cleanup Methods】
First remove all sources of ignition, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
1. VENTILATE AREA OF SPILL. 2. COLLECT SPILLED MATERIAL IN MOST CONVENIENT & SAFE MANNER FOR RECLAMATION OR FOR DISPOSAL IN SECURED SANITARY LANDFILL. LIQ ... SHOULD BE ABSORBED IN VERMICULITE, DRY SAND, EARTH, OR A SIMILAR MATERIA
【Transport】
UN 1145 3
【Fire Fighting Procedures】
In case of fire in the surroundings: all extinguishing agents allowed.
【Fire Potential】
Not combustible
【Reactivities and Incompatibilities】
Contact with strong oxidizing agents may cause fire and explosion.
【Other Preventative Measures】
Non-impervious clothing which becomes contaminated with molten or solid octachloronaphthalene or liquids containing octachloronaphthalene should be removed promptly and not reworn until the octachloronaphthalene is removed from the clothing.
If employess' clothing may have become contaminated with solid octachloronaphthalene, employees should change into uncontaminated clothing before leaving the work premises.
Clothing contaminated with octachloronaphthalene should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of octachloronaphthalene from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the octachloronaphthalene, the person performing the operation should be informed of octachloronaphthalene's hazardous properties.
CONDENSER IMPREGNATION & OTHER OPERATIONS INVOLVING MELTING OF CHLORONAPHTHALENE SHOULD BE ENCLOSED OR PROVIDED WITH EFFECTIVE LOCAL EXHAUST VENTILATION. /CHLORONAPHTHALENES/
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
The worker should immediately wash the skin when it becomes contaminated.
The worker should wash daily at the end of each work shift.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Employees should be provided with and required to use impervious clothing, gloves, face shields (eight inch minimmum), and other appropriate protective clothing necessary to prevent: any possibility of skin contact with molten octachloronaphthalene, repeated or prolonged skin contact with solid octachloronaphthalene or liquids containing octachloronaphthalene, or skin contact with octachloronaphthalene vapors from heated material.
... Wear appropriate clothing to prevent any possibility of skin contact with molten material ... /or/ solutions. Wear eye protection ... /and/ wash promptly when skin ... is contaminated. /Chloronaphthalenes/
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 1 mg/cu m: (Assigned protection factor = 10) Any supplied-air respirator/(Assigned protection factor = 50) Any self-contained breathing apparatus with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned protection factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode/(Assigned protection factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned protection factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter/Any appropriate escape-type, self-contained breathing apparatus.
【Octanol/Water Partition Coefficient】
log Kow = 8.5
【Report】

EPA Extremely Hazardous Substances List. Community Right-To-Know List. Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Recommendable method: Incineration. Peer-review: Ensure plentiful supply of hydrocarbon fuel. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Polychlorinated naphthalenes (PCNs) ... can be synthesized by the chlorination of naphthalene. /Polychlorinated naphthalenes/
U.S. Production

... Exact yearly or total production figures are obscure. In 1972, the estimated market for PCNs was less than 2300 metric tons. /Polychlorinated naphthalenes/

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
One day after a single intraperitoneal injection in mice of 1 mg per animal the highest concentration of octachloronaphthalene was found in the adipose tissue: 2.1% of the dose. Lower concentrations were found in the liver (1.9%), spleen (0.80%), and kidneys (0.32%). The concentration in adipose tissue increased gradually up to day 7.
Tissue distribution and biological half lives of 1,8-dichloronaphthalene), 2,7-dichloronaphthalene, and octachloronaphthalene were investigated in mice. Pathogen free male JCL/ICR mice were given a single ip dose of 1 mg of 5 mg/ml 1,8-dichloronaphthalene, 2,7-dichloronaphthalene, or octachloronaphthalene dissolved in olive oil. Controls were injected with vehicle only. Animals were killed by cervical dislocation 3 and 6 hr and 1, 3, 7, 14, and 28 days after injection. The brain, heart, lungs, liver, kidneys, testes, spleen, and adipose tissues were removed and the chloronaphthalenes were estimated by gas chromatography of tissue extracts. Biological half lives were calculated from elimination data. The highest percentage of each chloronaphthalene was found in the adipose tissue, attributable to lipophilic properties of chloronaphthalenes, and the lowest percentage was found in heart and brain tissues. The concentration of chloronaphthalenes in other tissues showed no fixed relationship. Octachloronaphthalene was present mostly in the adipose tissue, where little 1,8-dichloronaphthalene was present. The concentration of the three chloronaphthalenes, except for octachloronaphthalene in adipose tissues, increased to a maximum within 3 hr after dosing and decreased exponentially thereafter. The concentration of octachloronaphthalene increased gradually in adipose tissue up to day 7. The biological half life of 2,7-dichloronaphthalene was longer than that of 1,8-dichloronaphthalene in most of the tissues. It was concluded that the biological half life may be affected by the substituted position of chlorine in the chloronaphthalenes and that higher chlorinated naphthalenes are metabolized more slowly than lower chlorinated naphthalenes. [Oishi H, Oishi S; Toxicol Lett 15 (2-3): 119-122 (1983)] PubMed Abstract
The uptake and elimination of three superlipophilic compounds (hexabromobenzene, PCB153, and octachloronaphthalene) after dietary uptake was studied in earthworms (Eisenia andrei). All three compounds were taken up from the food, although they did not significantly accumulate despite their hydrophobicity. Both uptake efficiencies (E) and biomagnification factors (BMF) were low. E varied between 0.70 and 7.5%, while BMF values were all below 0.17. The elimination of the compounds was slow, with elimination rate constants k2 varying between 0.04 and 0.09/day. [Belfroid A et al; Ecotoxicol Environ Saf 31 (3): 185-91 (1995)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of octachloronaphthalene with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-14 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 830 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Octachloronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Octachloronaphthalene absorbs light with wavelengths >290 nm(4), and may be susceptible to direct photolysis by sunlight(SRC).

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