2-Chloronaphthalene

2-Chloronaphthalene Basic information
Product Name:2-Chloronaphthalene
Synonyms:2-Chlornaftalen;2-chloro-naphthalen;2-naphthylchloride;b-Chloronaphthalene;Halowax;2-Chloronaphthalene,99%;2-Chloronaphthalene 100mg [91-58-7];2-Chloronaphthalene, 99% 5GR
CAS:91-58-7
MF:C10H7Cl
MW:162.62
EINECS:202-079-9
Product Categories:Naphthalene derivatives;CHAnalytical Standards;Alpha Sort;C;CAlphabetic;Chemical Class;Naphthalenes;Volatiles/ Semivolatiles;OLED
Mol File:91-58-7.mol
2-Chloronaphthalene Structure
2-Chloronaphthalene Chemical Properties
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. Sealed in dry,Room Temperature
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 Constant3.31 x 10-4 atm?m3/mol at 25 °C (gas stripping-UV spectrophotometry, Shiu and Mackay, 1997)
CAS DataBase Reference91-58-7(CAS DataBase Reference)
NIST Chemistry ReferenceNaphthalene, 2-chloro-(91-58-7)
EPA Substance Registry System2-Chloronaphthalene (91-58-7)
Safety Information
Hazard Codes Xi,T,F
Risk Statements 36/37/38-39/23/24/25-23/24/25-11
Safety Statements 37/39-26-45-36/37-16-7
RIDADR UN1230 3/PG 2
WGK Germany 3
RTECS QJ2275000
HS Code 29039990
Hazardous Substances Data91-58-7(Hazardous Substances Data)
ToxicityAcute oral LD50 for rats 2,078 mg/kg, mice 886 mg/kg (quoted, RTECS, 1985).
MSDS Information
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2-Chloronaphthalene English
ACROS English
2-Chloronaphthalene Usage And Synthesis
Chemical PropertiesWHITE TO ALMOST WHITE CRYSTALLINE POWDER
Chemical PropertiesThe chlorinated naphthalenes in which one or more hydrogen atoms have been replaced by chlorine to form wax-like substances, beginning with monochloronaphthalene and going on to the octachlor derivatives.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:
UsesChlorinated naphthalenes were formerly used in the production of electric condensers, insulating electric condensers, electric cables, and wires; additive for high pressure lubricants.
Uses2-Chloronaphthalene 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.
Synthesis Reference(s)The Journal of Organic Chemistry, 39, p. 1317, 1974 DOI: 10.1021/jo00923a036
General DescriptionMonoclinic plates or off-white crystalline powder. Melting point 59.5°C.
Air & Water ReactionsInsoluble in water.
Reactivity Profile2-Chloronaphthalene may react with strong oxidizing agents .
Fire HazardFlash point data for 2-Chloronaphthalene are not available. 2-Chloronaphthalene is probably combustible.
Potential ExposureIndustrial 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 fateBiological. 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).

ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification MethodsDistil 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.]
IncompatibilitiesAll 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 DisposalHigh-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.
1-CHLOROPYRENE 2-CHLORO-9,10-BIS(PHENYLETHYNYL)ANTHRACENE CHLORINATED HYDROCARBONS MIXTURE Octachloronaphthalene 9-CHLOROPHENANTHRENE 2,4-DICHLORO-1-NAPHTHOL 2-Chloroanthracene 9,10-BIS(4-ETHOXYPHENYL)-2-CHLOROANTHRACENE 1,2,3,4-TETRACHLORONAPHTHALENE 9,10-Bis(4-methoxyphenyl)-2-chloroanthracene HALOFANTRINE Polychlorinated Biphenyls (PCBs) 1,2,3,4,5,6-HEXACHLORO-7-METHOXYNAPHTHA- LENE, TECH. Halofantrine hydrochloride 6-chloro-2-naphthol 2-CHLORONAPHTHALENE (D7) 2-Chloronaphthalene 2-CHLORO-9,10-DIPHENYLANTHRACENE

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