LINDANE CAS 58-89-9
Introduction：Basic information about LINDANE CAS 58-89-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
LINDANE Basic information
| Product Name: | LINDANE |
| Synonyms: | JUCUTIN(R);KEWLL(R);ISOTOX(R);LOREXANE(R);'LGC' (1103);'LGC' (1104);LINTOX(R);LINDANE |
| CAS: | 58-89-9 |
| MF: | C6H6Cl6 |
| MW: | 290.83 |
| EINECS: | 200-401-2 |
| Product Categories: | Organics;INSECTICIDE;Fluoroelastomer |
| Mol File: | 58-89-9.mol |
LINDANE Chemical Properties
| Melting point | 113-115 °C(lit.) |
| Boiling point | 373.64°C (rough estimate) |
| density | 1.7152 (rough estimate) |
| vapor pressure | 28.0, 55.3, 87.0, 168.8, 285.8, 297.0, and 538.5 at 19.58, 24.95, 28.42, 33.58, 37.82, 37.86, and43.32 °C, respectively (Boehncke et al., 1996) |
| refractive index | nD20 1.644 |
| Fp | 11 °C |
| storage temp. | 0-6°C |
| solubility | H2O: insoluble0.01g/L (practically) |
| Water Solubility | 7.3 mg l-1 (25 °C) |
| Merck | 13,5523 |
| BRN | 1907337 |
| Henry's Law Constant | 12.8 at 5 °C, 14.8 at 15 °C, 18.8 at 20 °C, 26.6 at 25 °C, 38.5 at 35 °C (gas stripping-GC, Cetin etal., 2006) |
| Exposure limits | NIOSH REL: TWA 0.5 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA0.5 mg/m3; ACGIH TLV: TWA 0.5 mg/m3. |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| IARC | 1 (Vol. 113) 2018 |
| NIST Chemistry Reference | Lindane(58-89-9) |
| EPA Substance Registry System | Lindane (58-89-9) |
Safety Information
| Hazard Codes | T,N,F,Xn,Xi |
| Risk Statements | 20/21-25-48/22-50/53-64-39/23/24/25-23/24/25-11-67-65-38-52/53-62-48/20-40-21 |
| Safety Statements | 36/37-45-60-61-62-33-29-16-9-7-22 |
| RIDADR | UN 2811 6.1/PG 1 |
| OEB | C |
| OEL | TWA: 0.5 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | GV4900000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 2903810000 |
| Hazardous Substances Data | 58-89-9(Hazardous Substances Data) |
| Toxicity | LD50 in male, female rats (mg/kg): 88, 91 orally (Gaines) |
| IDLA | 50 mg/m3 |
| Description | Lindane is one of eight different hexachlorocyclohexane(HCH), [58-89-9], C6H6Cl6, isomers andits Chemical Abstract name is 1α, 2α,3β,4α,5α,6β-hexachlorocyclohexane 58-89-9 (γ-HCH or γ -BHC, benzenehexachloride) (80). Commercial products containinglindane are marketed as either a mixture of isomersor as the pure γ -BHC isomer. Not unexpectedly, lindaneis a highly stable lipophilic compound and it hasbeen used extensively worldwide as an insecticide. Incontrast, hexachloropentadiene, [77-47-4], C5Cl6, is anextremely reactive industrial intermediate used as a chemicalintermediate in the synthesis of a broad range ofcyclodiene-derived pesticides, which include endosulfan,endrin, heptachlor, and several different organohalogenflame retardants (81). |
| Chemical Properties | white powder |
| Chemical Properties | Lindane is a white to yellow, crystalline powder with a slight, musty odor (pure material is odorless). |
| Chemical Properties | BHC is a white-to-brownish crystalline solidwith a musty, phosgene-like odor. |
| Physical properties | Colorless to yellow crystalline solid with a slight, musty, chlorinated-like odor. Odor thresholdconcentration is 12.0 mg/kg (Sigworth, 1964). Robeck et al. (1965) reported an odor threshold of330 ppb. |
| Originator | Kwell,Reed Carnrick,US,1952 |
| Uses | The only identified uses for hexachlorocyclohexane-containing products are based on the insecticidal activity of the γ isomer (lindane), which is considered to be the only insecticidally effective component (Extoxnet 1996). Lindane or technical-grade hexachlorocyclohexane containing the γ isomer is used primarily as an insecticide in the treatment of wood and wooden structures, seed grains, and livestock (ATSDR 2005, HSDB 2009). Other major uses are as an insecticide for several dozen fruit and vegetable crops, in baits and seed treatments for rodent control, and for treatment of scabies (mites) and lice. It is approved by the U.S. Food and Drug Administration foruse in three products for the treatment of lice and scabies (one lotionand two shampoos) (FDA 2009). Agricultural and pesticide uses accounted for about 270,000 kg (594,000 lb) of lindane and 450,000 kg (1 million pounds) of technical-grade hexachlorocyclohexane in 1974;the remaining uses were industrial or pharmaceutical (IARC 1979). |
| Uses | Pesticide and insecticide. |
| Definition | ChEBI: Beta-hexachlorocyclohexane is the beta-isomer of hexachlorocyclohexane. It has a role as a persistent organic pollutant. It is an organochlorine pesticide and a hexachlorocyclohexane. |
| Indications | Lindane (Gamma benzene hexachloride, Kwell, Thionex) is a cyclic chlorinatedhydrocarbon originally developed as an agricultural insecticide. It is absorbedthrough the chitinous exoskeleton and stimulates the nervous system, resulting inseizures and death of the insect. It is both a pediculicide and scabicide, with a45% to 70% ovicidal effect. Resistance has been shown to Pediculosis capitis andSarcoptes scabiei. Lindane can be absorbed through intact skin following topicalapplication and has the potential for CNS toxicity. It should therefore be used withgreat caution in infants, children <2 years of age, elderly patients, and pregnantand lactating women. It may be irritating to the eyes or mucous membranes; hence,these areas should be avoided. Irritant dermatitis may occur with use of excessive amounts or over prolonged periods. Toxicity, if overused, may result in nausea,vomiting, seizures, or even bone marrow suppression. Lindane is an organochlorine with very slow onset of action and poor ovicidal activity;it takes over 3 hours to kill the lice during which increased lice crawling andtwitching can cause increased pruritus for the patient. Lindane is available as ashampoo for the treatment of pediculosis capitis and/or pubis and in cream andlotion form for treating scabies and all forms of pediculosis. GBH also repelsticks and other arthropods and kills chiggers. |
| Manufacturing Process | Chlorine gas was gradually passed into 660 parts of benzene contained in alead-lined reaction vessel until 890 parts of the gas had been absorbed. Themixture was stirred continuously and the temperature maintained at 15°C to20°C. The supply of chlorine was then interrupted and the precipitated solid filteredoff and dried. In weight, it was found to be equivalent to 900 parts. Themother liquid was then mixed with 330 parts of benzene and the mixtureagain treated with 890 parts of chlorine in the manner described. After filtering the reaction mixture resulting from the second chlorination, thefiltrate was again mixed with a smaller quantity of benzene and againchlorinated in a similar manner. In this way, a continuous process for thepreparation of benzene hexachloride resulted. That benzene hexachloride isomer mixture is then the raw material for lindaneproduction. The production of lindane per se is not a chemical synthesisoperation but a physical separation process. It is possible to influence thegamma isomer content of benzene hexachloride to an extent during thesynthesis process. Basically, however, one is faced with the problem ofseparating a 99%-plus purity gamma isomer from a crude product containingperhaps 12 to 15% of the gamma isomer. The separation and concentrationprocess is done by a carefully controlled solvent extraction and crystallizationprocess. One such process is described by R.D. Donaldson et al. Anotherdescription of hexachlorocyclohexane isomer separation is given by R.H.Kimball. |
| Brand name | Benhexachlor;Gamex;Gamma benzene;Hexachloride. |
| Therapeutic Function | Pediculicide, Scabicide |
| World Health Organization (WHO) | Lindane has been available for more than 25 years and is widelyused as an agricultural and household pesticide. |
| General Description | Colorless solid with a musty odor; pure material is odorless. Used as a pesticide and scabicide. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | LINDANE is incompatible with strong bases. LINDANE is incompatible with powdered metals such as iron, zinc and aluminum. LINDANE is also incompatible with oxidizing agents. LINDANE can undergo oxidation when in contact with ozone. When exposed to alkalis, LINDANE undergoes dehydrochlorination. |
| Health Hazard | LINDANE is a stimulant of the nervous system, causing violent convulsions that are rapid in onset and generally followed by death or recovery within 24 hours. The probable human oral lethal dose is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150-lb (70 kg) person. |
| Health Hazard | High acute toxicity; symptoms — headache,dizziness, nausea, vomiting, diarrhea, tremor,cyanosis, epileptic convulsions; stimulant tonervous system, which can lead to violent convulsions; such convulsions may setrapidly that may either progress to recovery within 24 hours or could lead to death(Hayes 1982); ingestion of 2–10 g probably fatal to human; an irritant to eyeand skin; chronic exposure causes liverinjury; oral LD50 value (mice): 86 mg/kg;carcinogenic to animals, causing liver andlung tumors; exposure limit: TLV : TWA(skin) 0.5 mg/m3 (ACGIH, MSHA, andOSHA); RCRA Waste Number U120. |
| Fire Hazard | When heated to decomposition, LINDANE emits toxic fumes of chlorine, hydrochloric acid, and phosgene. |
| Agricultural Uses | Insecticide, Rodenticide: Lindane has been used against insects in a widerange of applications including treatment of animals,buildings, man for ectoparasites, clothes, water for mosquitoes,living plants, seeds and soils. Most applicationshave been canceled due to excessive residues, e.g., storedfoodstuffs, that may cause cancer. Formulators, distributorsand users of lindane represent a special risk group.The major use of lindane in recent years has been to pretreatseeds. Other uses include sunflowers, peas, wheat,barley and oats. Lindane is currently also used in lotions,creams and shampoos for the control of lice and mitesin humans. Not approved for use in EU countries. AU.S. EPA restricted Use Pesticide (RUP). Lindane shouldbe handled as a carcinogen, with extreme caution. Mostapplications have been canceled. It has not been producedin the U.S. since 1977; however, it is still imported intothe U.S. and formulated to treat head lice, body lice andscabies. |
| Trade name | AALINDAN®; AFICIDE®;AGRISOL G-20®; AGROCIDE®; AGRONEXIT®;AMEISENATOD®; AMEISENMITTEL (MERCK)®;APARASIN®; APHTIRIA®; APLIDAL®; ARBITEX®;BEN-HEX®; BENTOX 10®; CELANEX®;CHLORESENE®; CODECHINE®; DELSANEXDAIRY FLY SPRAY®; DETMOL-EXTRAKT®; DETOX25®; DEVORAN®; DOL GRANULE®; DRILL TOXSPEZIALAGLUKON®; DUAL MURGANIC RPB SEEDTREATMENT®; ENTOMOXAN®; EXAGAMA®;FORLIN®; GALLOGAMA®; GAMACID®;GAMAPHEX®; GAMENE®; GAMMA-COL®;GAMMALIN®; GAMMALIN 20; GAMMALEX®;GAMMASAN 30®; GAMMATERR®; GAMMAPHEX®;GAMMEX®; GAMMEXANE®; GAMMEXENE®;GAMMOPAZ®; GEXANE®; HECLOTOX®; HEXA®;HEXAFLOW®; HEXATOX®; HEXAVERM®;HEXICIDE®; HEXYCLAN®; HORTEX®; INEXIT®;ISOTOX®; JACUTIN®; KOKOTINE®; KWELL®;LENTOX®; LINDAGRAM®; LIDENAL®; LINDAFOR®;LINDAGAM®; LINDAGRAIN®; LINDAGRANOX®;LINDAPOUDRE®; LINDATOX®; LINDOSEP®;LINTOX®; LOREXANE®; MARSTAN FLY SPRAY®;MERGAMMA 30®; MILBOL 49®; MIST-O-MATICLINDEX®; MSZYCOL®; NEXEN FB®; NEXIT®;NEXIT-STARK®; NEXOL-E®; NICOCHLORAN®;NOVIGAM®; OMNITOX®; OVADZIAK®;OWADZIAK®; PEDRACZAK®; PFLANZOL®;QUELLADA®; RODESCO INSECT POWDER®;SANG GAMMA®; SILVANO®; SPRITZ-RAPIDIN®;SPRUEHPFLANZOL®; STREUNEX®; TAP 85®; TRI-6®; VITON® |
| Contact allergens | Lindane is a pesticide used for its antiinsect properties in agriculture, wood protection, in antiinsect paints and veterinary and human medicine against many and veterinary and human medicine against many and demodicidosis. Its use is controlled, particularlybecause of neurological toxicity |
| Clinical Use | Lindane is 1,2,3,4,5,6-hexachlorocyclohexane, -benzenehexachloride, or benzene hexachloride (Kwell, Scabene,Kwildane, G-Well). This halogenated hydrocarbon is preparedby the chlorination of benzene. A mixture of isomersis obtained in this process, five of which have been isolated:α, β, γ, δ, and ε. The γ-isomer, present to 10% to 13% inthe mixture, is responsible for the insecticidal activity. The -isomer may be separated by various extraction and chromatographictechniques.Lindane occurs as a light buff to tan powder with a persistentmusty odor, and it is bitter. It is insoluble in water butsoluble in most organic solvents. It is stable under acidic orneutral conditions but undergoes elimination reactions underalkaline conditions.The action of lindane against insects is threefold: it is a directcontact poison, it has a fumigant effect, and it acts as astomach poison. The effect of lindane on insects is similar tothat of DDT. Its toxicity in humans is somewhat lower thanthat of DDT. Because of its lipid solubility properties, however,lindane when ingested tends to accumulate in the body.Lindane is used locally as a cream, lotion, or shampoo forthe treatment of scabies and pediculosis. |
| Safety Profile | Confirmed carcinogenwith experimental carcinogenic andneoplastigenic data. A human systemicpoison by ingestion. Also a poison byingestion, skin contact, intraperitoneal,intravenous, and intramuscular routes.Human systemic effects by ingestion:convulsions, dyspnea, and cyanosis.Experimental teratogenic and reproductiveeffects. Mutation data reported. See alsoBENZENE HEXACHLORIDE and otherbenzene hexachloride entries. When heatedto decomposition it emits toxic fumes ofCl-, HCl, and phosgene. |
| Potential Exposure | The major commercial usage of BHCis based upon its insecticidal properties. α-BCH is used asan Agricultural chemical, pesticide, pharmaceutical, andveterinary drug. The 7-isomer has the highest acute toxic ity, but the other isomers are not without activity. It is gen erally advantageous to purify the 7-isomer from the lessactive isomers. The γ-isomer acts on the nervous system ofinsects, principally at the level of the nerve ganglia. As aresult, lindane has been used against insects in a wide rangeof applications including treatment of animals, buildings,humans for ectoparasites, clothes; water for mosquitoes;living plants; seeds and soils. Some applications have beenabandoned due to excessive residues, e.g., stored food stuffs. By voluntary action, the principal domestic producerof technical grade BHC requested cancellation of its BHCregistrations on September 1, 1976. As of July 21, 1978, allregistrants of pesticide products containing BHC voluntar ily canceled their registrations or switched their formerBHC products to lindane formulations. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. |
| Carcinogenicity | Lindane (as γ-hexachlorocyclohexane), hexachlorocyclohexane (technical grade), and other hexachlorocyclohexane isomers are reasonably anticipated to be human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals. |
| Environmental Fate | Biological. In a laboratory experiment, a strain of Pseudomonas putida culture transformedlindane to g-3,4,5,6-tetrachlorocyclohexane (g-TCCH), g-pentachlorocyclohexane(g-PCCH) and a-BHC (Benezet and Matsumura, 1973). g-TCCH was also reported as aproduct of lindane degradation by Clostridium sphenoides (MacRae et al., 1969; Heritageand MacRae, 1977, 1977a), an anaerobic bacterium isolated from flooded soils (MacRaeet al., 1969; Sethunathan and Yoshida, 1973a). Lindane degradation by Escherichia colialso yielded g-PCCH (Francis et al., 1975). Evidence suggests that degradation of lindanein anaerobic cultures or flooded soils amended with lindane occurs via reductive dehalogenationproducing chlorine-free volatile metabolites (Sethunathan and Yoshida, 1973a). After a 30-day incubation period, the white rot fungus Phanerochaete chrysosporiumconverted lindane to carbon dioxide. Mineralization began between the third and sixth dayof incubation. The production of carbon dioxide was highest between 3 to 18 days o Beland et al. (1976) studied the degradation of lindane in sewage sludge under anaerobicconditions. Lindane underwent reductive hydrodechlorination forming 3,4,5,6-tetrachlorocyclohex-1-ene (g-BTC). The amount of g-BTC that formed reached a maximumconc When lindane was incubated in aerobic and anaerobic soil suspensions for 3 weeks,0 and 63.8% was lost, respectively (MacRae et al., 1984). Using settled domestic wastewaterinoculum, lindane (5 and 10 mg/L) did not degrade after 28 days of incubation at25°C (Tabak et al., 1981). Soil. In moist soils, lindane biodegraded to g-pentachlorocyclohexene (Elsner et al.,1972; Kearney and Kaufman, 1976; Fuhremann and Lichtenstein, 1980). Under anaerobicconditions, degradation by soil bacteria yielded g-BTC and a-BHC (Kobayashi |
| Metabolic pathway | The metabolic pathways of gamma-HCH are complex and more than 80metabolites have been identified (Macholz and Kujawa, 1985). Dehydrohalogenationreactions are important. Gamma-HCH may be convertedinto other HCH isomers in the environment and also microorganisms andplants may convert gamma-HCH (1) into the alpha (2), beta (3), or delta(4) isomers (see Schemel). Bioisomerisation does not appear to be a significantpathway in mammals. In animals, metabolism of gamma-HCHgenerally leads to less-chlorinated, unsaturated metabolites. Chlorinatedphenols may be formed and excreted as glucuronides. In a detailed discussionof the biodegradation of gamma-HCH, the reaction mechanismsinvolved were critically reviewed (Kurihara and Nakajima, 1980).Oxygenation or glutathione conjugation are important initial stages inmetabolism. Key intermediates in the metabolic pathways are hexachlorocyclohexene(18), pentachlorocyclohexene (5) and tetrachlorocyclohexene(6) and these have been identified in a number of organisms(Macholz and Kujawa, 1985). |
| Solubility in water | Wt % at 20 °C: 30.31 in acetone, 22.42 in benzene, 19.35 in chloroform, 17.22 in ether, 6.02 inethanol (Windholz et al., 1983) 9.76 and 13.97 g/L in hexane at 10 and 20 °C, respectively (shake flask-GC, Mills and Biggar,1969) 92.8 g/kg in triolein at 25 °C (Chiou and Manes, 1986) |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly sealed containers in a cool, dryplace away from light and incompatible materials. Protectcontainers against physical damage. A regulated, markedarea should be established where this chemical is handled,used, or stored in compliance with OSHA Standard1910.1045. |
| Shipping | UN2761 Organochlorine pesticides, solid, toxic,Hazard Class: 6.1; Labels: 6.1-Poisonous materials. |
| Purification Methods | Crystallise it from EtOH. Purify it also by zone melting. Possible CANCER AGENT, TOXIC. [: Beilstein 1 H 23, : Beilstein 5 I 8, many isomers : Beilstein 5 III 41, 5 IV 55.] |
| Toxicity evaluation | The acute toxicity of lindane depends on the age, sex, andanimal species, and on the route of administration. Theoral LD50 in mice, rats, and guinea pigs is 86, 125–230,and 100–127 mg/kg, respectively. In contrast, most ofthe other isomers were considerably more toxic (94,95).Some of the other toxic responses caused by lindane inlaboratory animals include hepato- and nephrotoxicity,reproductive and embryotoxicity, mutagenicity in someshort-term in vitro bioassays, and carcinogenicity (80). Themechanism of the lindane-induced response is not known.Only minimal data are available on the mammaliantoxicities of hexachlorocyclopentadiene. |
| Degradation | Gamma-HCH is extremely stable to light, air, temperatures up to 180 °C,and to acids. It undergoes dechlorination in alkalis with DT50 values(22 °C) of 191 days (pH 7) and 11 hours (pH 9). It is photodegraded inorganic solvents (2-propanol or methanol) by UV irradiation (254 nm). |
| Incompatibilities | Lindane decomposes on contact withpowdered iron, aluminum, and zinc and with alkalis producing trichlorobenzene. Corrosive to metals |
| Waste Disposal | For the disposal of lindane, aprocess has been developed involving destructive pyrolysis@ 400-500℃ with a catalyst mixture which contains5%-10% of either cupric chloride, ferric chloride; zincchloride; or aluminum chloride on activated carbon.Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of wastecontaining this contaminant (≥100 kg/mo) must conformwith EPA regulations governing storage, transportation,treatment, and waste disposal. |
LINDANE Preparation Products And Raw materials
| Raw materials | Benzene-->Chlorine-->Tetrachlorvinphos-->CYCLOHEXANE-D12-->BETA-HCH-->CHLORDENE |
