| Identification | More | [Name]
2-Chloronaphthalene | [CAS]
91-58-7 | [Synonyms]
2-CHLORONAPHTHALENE
BETA-CHLORONAPHTHALENE
β-Chloronaphthalene
PCN-2
2-Chlornaftalen
2-chloro-naphthalen
2-naphthylchloride
beta-chloronaphthalene[qr]
halowax[qr]
naphthalene,2-chloro-
naphthalene,2-chloro-[qr]
Rcra waste number U047
rcrawastenumberu047
Chloronaphthalene, beta
2-CHLORONAPHTHALENE, 1X1ML, MEOH, 5000UG /ML
2-CHLORONAPHTHALENE, 1000MG, NEAT
2-Cholronaphthalene
2-chloronaphthalene solution
2-CHLORONAPHTALENE
2-Chlornaphthalin | [EINECS(EC#)]
202-079-9 | [Molecular Formula]
C10H7Cl | [MDL Number]
MFCD00035731 | [Molecular Weight]
162.62 | [MOL File]
91-58-7.mol |
| Chemical Properties | Back Directory | [Appearance]
The chlorinated naphthalenes in which one or
more hydrogen atoms have been replaced by chlorine to
form wax-like substances, beginning with monochloronaphthalene and going on to the octachlor derivatives.
Their physical states vary from mobile liquids to waxysolids depending on the degree of chlorination; freezing/
melting points of the pure compounds range from 17C
for 1-chloronaphthalene to 198C for 1,2,3,4-
tetrachloronaphthalene.
1-Chloro-isomer: Hazard identification (based on
NFPA-704 M Rating System): Health 2, flammability 1,
reactivity 0.
2-Chloro-isomer: | [Melting point ]
57-60 °C
| [Boiling point ]
256 °C
| [density ]
1.1377 | [vapor pressure ]
0.40 at 59.0 °C (Verevkin, 2003) | [refractive index ]
1.6079 | [Fp ]
125 °C
| [storage temp. ]
2-8°C | [solubility ]
Soluble in chloroform, carbon disulfide (Windholz et al., 1983), and many other halogenated
liquid solvents (e.g., methylene chloride). | [form ]
Crystalline Powder | [color ]
White to almost white | [Water Solubility ]
insoluble | [Merck ]
2150 | [Henry's Law Constant]
3.31 x 10-4 atm?m3/mol at 25 °C (gas stripping-UV spectrophotometry, Shiu and Mackay, 1997) | [Dielectric constant]
5.0（24℃） | [CAS DataBase Reference]
91-58-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Naphthalene, 2-chloro-(91-58-7) | [EPA Substance Registry System]
2-Chloronaphthalene (91-58-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN1230 3/PG 2 | [WGK Germany ]
3 | [RTECS ]
QJ2275000 | [HS Code ]
29039990 | [Hazardous Substances Data]
91-58-7(Hazardous Substances Data) | [Toxicity]
Acute oral LD50 for rats 2,078 mg/kg, mice 886 mg/kg (quoted, RTECS, 1985). |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Naphthalene, 2-(triethylsilyl)--->Cycloprop[a]indene, 1,1-dichloro-1,1a,6,6a-tetrahydro--->1,2,4,6-TETRACHLORONAPHTHALENE-->1,2,4,7-TETRACHLORONAPHTHALENE-->1,2,7-TRICHLORONAPHTHALENE-->1,2,3,4,6-PENTACHLORONAPHTHALENE-->1,3-dichloronaphthalene-->Naphthalene, 1,2,4-trichloro--->2,3-dimethyl-1H-indene-->1,2,3,4-TETRACHLORONAPHTHALENE | [Preparation Products]
1-Chloronaphthalene |
| Hazard Information | Back Directory | [Chemical Properties]
2-Chloronaphthalene(91-58-7) is a white to almost white crystalline powder and is practically insoluble in water. The chlorinated naphthalenes, which are derived from naphthalene through the replacement of one or more hydrogen atoms by chlorine, result in the formation of wax-like substances. This process starts with monochloronaphthalene and continues to the octachlor derivatives. The physical state of these substances can vary from mobile liquids to waxy solids, depending on the degree of chlorination. The freezing/melting points of the pure compounds range from 17°C for 1-chloronaphthalene to 198°C for 1,2,3,4-tetrachloronaphthalene.
| [Uses]
2-Chloronaphthalene(91-58-7) was used as a reagent in the enantioselective synthesis of heterocyclic ketones with α-chiral quaternary stereocentres. When used as a processing additive in bulk heterojunction solar cells, it doubles its power conversion efficiency.
| [Application]
2-Chloronaphthalene(91-58-7) can be used to:
As an inducer, it was shown that 2-chloronaphthalene is a potent inducer of cytochrome p450 activity.
As a synthetic raw material, 2-chloronaphthalene is used as an intermediate in organic synthesis and as a precursor for other compounds in the synthesis of malonic acid.
As a biological research reagent, 2-chloronaphthalene is used in experimental studies of biodegradation and metabolism in Pseudomonas aeruginosa[1-2].
| [Reactions]
2-Chloronaphthalene may react with strong oxidizing agents. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 39, p. 1317, 1974 DOI: 10.1021/jo00923a036 | [General Description]
Monoclinic plates or off-white crystalline powder. Melting point 59.5°C. | [Air & Water Reactions]
Insoluble in water. | [Reactivity Profile]
2-CHLORONAPHTHALENE(91-58-7) may react with strong oxidizing agents. | [Health Hazard]
2-Chloronaphthalene is a strong irritant. It may be absorbed through the skin. When heated to decomposition, toxic fumes of chlorides are released. Prolonged exposure to such compounds may cause symptoms such as chloracne, cysts, headaches, fatigue, dizziness, anorexia and jaundice. | [Fire Hazard]
Flash point data for 2-Chloronaphthalene are not available. 2-Chloronaphthalene is probably combustible. | [Potential Exposure]
Industrial exposure from individual
chlorinated naphthalenes is rarely encountered; rather it
usually occurs from mixtures of two or more Chlorinated
naphthalenes. Due to their stability, thermoplasticity, and
nonflammability, these compounds enjoy wide industrial
application. These compounds are used in the production of
electric condensers; in the insulation of electric cables and
wires; as additives to extreme pressure lubricants; as supports for storage batteries; and as a coating in foundry use.
octachloro-: Used as a fireproof and waterproof additive
and lubricant additive. Pentachloro-: Used in electric wire
insulation and in additives to special lubricants. tetrachloro-: Used in electrical insulating materials and as an
additive in cutting oils. trichloro-: Used in lubricants and
in the manufacture of insulation for electrical wire.
Because of the possible potentiation of the toxicity of higher Chlorinated naphthalenes by ethanol and carbon tetrachloride, individuals who ingest enough alcohol to result in
liver dysfunction would be a special group at risk.
Individuals, e.g., analytical and synthetic chemists, mechanics and cleaners, who are routinely exposed to carbon tetrachloride or other hepatotoxic chemicals would also be at a
greater risk than a population without such exposure.
Individuals involved in the manufacture, utilization, or disposal of polychlorinated naphthalenes would be expected to
have higher levels of exposure than the general population. | [Environmental Fate]
Biological. Reported biodegradation products include 8-chloro-1,2-dihydro-1,2-
dihydroxynaphthalene and 3-chlorosalicylic acid (Callahan et al., 1979). When 2-chloronaphthalene
was statically incubated in the dark at 25 °C with yeast extract and settled domestic
wastewater inoculum, complete biodegradation was observed after 7 d (Tabak et al., 1981).
Chemical/Physical. The hydrolysis rate constant for 2-chloronaphthalene at pH 7 and 25 °C was
determined to be 9.5 x 10-6/h, resulting in a half-life of 8.3 yr (Ellington et al., 1988). At 85.5 °C,
hydrolysis half-lives of 255, 156, and 244 d were reported at pH values of 2.93, 7.10, and 9.58,
respectively (Ellington et al., 1977).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 280, 96, 33, and 11 mg/g, respectively (Dobbs and Cohen, 1980). | [Shipping]
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. | [Purification Methods]
Distil 2-chloronaphthalene in a vacuum, then crystallise it from 25% EtOH/water, then dry it under vacuum (see also the 1-isomer above). [Beilstein 5 H 541, 5 I 262, 5 II 445, 5 III 1573, 5 IV 1660.] | [Incompatibilities]
All are incompatible with oxidizers
(chlorates, nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, epoxides. Keep away from
heat. Penta- is also incompatible with acids, alkalis. | [Waste Disposal]
High-temperature incineration
with flue gas scrubbing. 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. | [References]
[1] MORRIS C, BARNSLEY E A. The cometabolism of 1- and 2-chloronaphthalene by pseudomonads[C]. 1900. DOI:10.1139/M82-005.
[2] JIAN YU. The Biodegradation Experiment of 1-chloronaphthalene and 2-chloronaphthalene[J]. 2012 International Conference on Biomedical Engineering and Biotechnology, 2012. DOI:10.1109/ICBEB.2012.399.
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