LINDANE
- CAS No.
- 58-89-9
- Chemical Name:
- LINDANE
- Synonyms
- 666;HCH;GAMMA-HCH;plk;G-BHC;DELTA-HCH;Viton;HGI;GAMMA-BHC;BBH
- CBNumber:
- CB5281877
- Molecular Formula:
- C6H6Cl6
- Molecular Weight:
- 290.81
- MOL File:
- 58-89-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/3/14 15:18:26
| 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 |
| Flash point | 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 et al., 2006) |
| Exposure limits | NIOSH REL: TWA 0.5 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA 0.5 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
Risk and Safety Statements
| Symbol(GHS) |    GHS06,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301-H312+H332-H362-H373-H410 | |||||||||
| Precautionary statements | P260-P263-P273-P280-P301+P310-P302+P352+P312 | |||||||||
| 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 | |||||||||
| OEB | C | |||||||||
| OEL | TWA: 0.5 mg/m3 [skin] | |||||||||
| RIDADR | UN 2811 6.1/PG 1 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | GV4900000 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 2903810000 | |||||||||
| Toxicity | LD50 in male, female rats (mg/kg): 88, 91 orally (Gaines) | |||||||||
| IDLA | 50 mg/m3 | |||||||||
| NFPA 704 |
|
LINDANE Chemical Properties,Uses,Production
Description
Lindane is one of eight different hexachlorocyclohexane (HCH), [58-89-9], C6H6Cl6, isomers and its Chemical Abstract name is 1α, 2α,3β,4α,5α,6β- hexachlorocyclohexane 58-89-9 (γ-HCH or γ -BHC, benzene hexachloride) (80). Commercial products containing lindane are marketed as either a mixture of isomers or as the pure γ -BHC isomer. Not unexpectedly, lindane is a highly stable lipophilic compound and it has been used extensively worldwide as an insecticide. In contrast, hexachloropentadiene, [77-47-4], C5Cl6, is an extremely reactive industrial intermediate used as a chemical intermediate in the synthesis of a broad range of cyclodiene-derived pesticides, which include endosulfan, endrin, heptachlor, and several different organohalogen flame retardants (81).
Chemical Properties
Lindane is a white to yellow, crystalline powder with a slight, musty odor (pure material is odorless).
Physical properties
Colorless to yellow crystalline solid with a slight, musty, chlorinated-like odor. Odor threshold concentration is 12.0 mg/kg (Sigworth, 1964). Robeck et al. (1965) reported an odor threshold of 330 ppb.
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).
Indications
Lindane (Gamma benzene hexachloride, Kwell, Thionex) is a cyclic chlorinated
hydrocarbon originally developed as an agricultural insecticide. It is absorbed
through the chitinous exoskeleton and stimulates the nervous system, resulting in
seizures and death of the insect. It is both a pediculicide and scabicide, with a
45% to 70% ovicidal effect. Resistance has been shown to Pediculosis capitis and
Sarcoptes scabiei.
Lindane can be absorbed through intact skin following topical
application and has the potential for CNS toxicity. It should therefore be used with
great caution in infants, children <2 years of age, elderly patients, and pregnant
and 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 and
twitching can cause increased pruritus for the patient. Lindane is available as a
shampoo for the treatment of pediculosis capitis and/or pubis and in cream and
lotion form for treating scabies and all forms of pediculosis. GBH also repels
ticks and other arthropods and kills chiggers.
World Health Organization (WHO)
Lindane has been available for more than 25 years and is widely used 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.
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 wide range of applications including treatment of animals, buildings, man for ectoparasites, clothes, water for mosquitoes, living plants, seeds and soils. Most applications have been canceled due to excessive residues, e.g., stored foodstuffs, that may cause cancer. Formulators, distributors and users of lindane represent a special risk group. The major use of lindane in recent years has been to pretreat seeds. 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 mites in humans. Not approved for use in EU countries. A U.S. EPA restricted Use Pesticide (RUP). Lindane should be handled as a carcinogen, with extreme caution. Most applications have been canceled. It has not been produced in the U.S. since 1977; however, it is still imported into the U.S. and formulated to treat head lice, body lice and scabies.
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 carcinogen with experimental carcinogenic and neoplastigenic data. A human systemic poison by ingestion. Also a poison by ingestion, skin contact, intraperitoneal, intravenous, and intramuscular routes. Human systemic effects by ingestion: convulsions, dyspnea, and cyanosis. Experimental teratogenic and reproductive effects. Mutation data reported. See also BENZENE HEXACHLORIDE and other benzene hexachloride entries. When heated to decomposition it emits toxic fumes of Cl-, HCl, and phosgene.
Potential Exposure
The major commercial usage of BHC is based upon its insecticidal properties. α-BCH is used as an Agricultural chemical, pesticide, pharmaceutical, and veterinary 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 less active isomers. The γ-isomer acts on the nervous system of insects, principally at the level of the nerve ganglia. As a result, lindane has been used against insects in a wide range of applications including treatment of animals, buildings, humans for ectoparasites, clothes; water for mosquitoes; living plants; seeds and soils. Some applications have been abandoned due to excessive residues, e.g., stored food stuffs. By voluntary action, the principal domestic producer of technical grade BHC requested cancellation of its BHC registrations on September 1, 1976. As of July 21, 1978, all registrants of pesticide products containing BHC voluntar ily canceled their registrations or switched their former BHC products to lindane formulations.
Carcinogenicity
Lindane (as γ-hexachlorocyclohexane), hexachlorocyclohexan e (technical grade), and other hexachlorocyclohexane isomers are reasonably anticipated to be human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals.
Metabolic pathway
The metabolic pathways of gamma-HCH are complex and more than 80 metabolites have been identified (Macholz and Kujawa, 1985). Dehydrohalogenation reactions are important. Gamma-HCH may be converted into other HCH isomers in the environment and also microorganisms and plants may convert gamma-HCH (1) into the alpha (2), beta (3), or delta (4) isomers (see Schemel). Bioisomerisation does not appear to be a significant pathway in mammals. In animals, metabolism of gamma-HCH generally leads to less-chlorinated, unsaturated metabolites. Chlorinated phenols may be formed and excreted as glucuronides. In a detailed discussion of the biodegradation of gamma-HCH, the reaction mechanisms involved were critically reviewed (Kurihara and Nakajima, 1980). Oxygenation or glutathione conjugation are important initial stages in metabolism. 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).
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.]
Incompatibilities
Lindane decomposes on contact with powdered iron, aluminum, and zinc and with alkalis producing trichlorobenzene. Corrosive to metals
Waste Disposal
For the disposal of lindane, a process has been developed involving destructive pyrolysis @ 400-500℃ with a catalyst mixture which contains 5%-10% of either cupric chloride, ferric chloride; zinc chloride; or aluminum chloride on activated carbon. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
LINDANE Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Super Crop Safe Limited | +91-9726022444 +91-9824169514 | Gujarat, India | 38 | 58 | Inquiry |
| High Grade Industries India Private Limited | 08068442243Ext 698 | Mumbai, India | 14 | 58 | Inquiry |
| Nakoda Corporation | 08048959416 | Madhya Pradesh, India | 16 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | China | 49391 | 58 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29826 | 58 | Inquiry |
| Hefei TNJ Chemical Industry Co.,Ltd. | 0551-65418671 | China | 34571 | 58 | Inquiry |