(1S,2R,3R,4S,6R,7R)-1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.02,6]dec-8-ene | 57-74-9

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机氯杀虫剂
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (1S,2R,3R,4S,6R,7R)-1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.02,6]dec-8-ene
• CAS: 57-74-9
• 化学式: C₁₀H₆Cl₈
• 分子量: 409.8
• InChiKey: BIWJNBZANLAXMG-DPSYREKSSA-N

物化性质

• 熔点：
  106-108℃
• 沸点：
  492.46°C (rough estimate)
• 密度：
  1.80
• 闪点：
  11 °C
• 溶解度：
  Miscible with acetone, cyclohexanone, deodorized kerosene, ethanol, 2-propanol, trichloroethylene (Worthing and Hance, 1991)
• 暴露限值：
  NIOSH REL: IDLH 0.5 mg/m3, IDLH 100 mg/m3; OSHA PEL: TWA 0.5 mg/m3; ACGIH TLV: TWA 0.5 mg/m3, STEL 2 mg/m3.
• 物理描述：
  TECHNICAL-GRADE PRODUCT: LIGHT YELLOW-TO-AMBER VISCOUS LIQUID.
• 颜色/状态：
  Viscous, amber-colored liquid
• 气味：
  PENETRATING; AROMATIC; SLIGHTLY PUNGENT, LIKE CHLORINE
• 蒸汽密度：
  14: (air= 1 at boiling point of chlordane)
• 蒸汽压力：
  9.75X10-6 mm Hg @ 25 °C
• 亨利常数：
  2.93e-04 atm-m3/mole
• 稳定性/保质期：
  Dehydrohalogenates in presence of alkali
• 分解：
  Hazardous decomposition products: Toxic gases and vapors, such as hydrogen chloride, chlorine, phosgene, and carbon monoxide. ...
• 粘度：
  69 poises at 25 °C (about that of 95% glycerol); viscosity reduced by heating to 120-140 °F
• 燃烧热：
  -4,000 BTU/LB= -2,200 CAL/G= -93X10+5 JOULES/KG (EST)
• 表面张力：
  LIQUID SURFACE TENSION: 25 DYNES/CM= 0.025 N/M @ 20 °C (EST)
• 气味阈值：
  Odor low: 0.0084 mg/cu m; Odor high: 0.0419 mg/cu m
• 折光率：
  Index of refraction: 1.56-1.57 @ 25 °C/D

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

在每隔一天口服处理28天的实验鼠中，技术级氯丹的cis-和trans-氯丹在第一天就达到了全身的最高水平，尽管反复给药，但下降到了较低的水平；cis-和trans-非氯丹以及过氧氯丹在整个研究期间呈增加趋势。测试样本中cis-与trans-氯丹的比例以及cis-与trans-非氯丹的比例（分别为6:7和1:4）以及在实验结束时小鼠体内的比例（分别为5:3和1:7）表明，trans-氯丹比cis-氯丹更易被代谢，而cis-非氯丹比trans-非氯丹更易被代谢。随着反复给药，氯丹异构体的含量减少，而过氧氯丹的含量增加，这表明氯丹能够诱导其自身的代谢。

In mice treated orally every other day for 28 days with technical chlordane, cis- and trans-chlordane reached peak levels in the whole body on the first day and declined to lower levels in spite of repeated dosing; cis- and trans-nonachlor and oxychlordane increased during the entire study period. The ratio of cis- to trans-chlordane and cis- to trans-nonachlor in the test sample (6:7 and 1:4, respectively) and in the mouse body at termination of the experiment (5:3 and 1:7, respectively) suggests that trans-chlordane is metabolized more readily than cis-chlordane and that cis-nonachlor is metabolized more readily than trans-nonachlor. The decreasing content of the chlordane isomers and the increasing content of oxychlordane with repeated dosing suggests that chlordane induces its own metabolism.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氯化丹（chlordane）和氧化氯丹通过大鼠肝微粒体的代谢在体外进行了研究。从雄性Sprague-Dawley大鼠制备的肝微粒体在37°C下与12.3纳米摩尔氯化丹一起孵化15分钟，在有或没有还原型NADPH生成系统的存在下，在空气或氮气或一氧化碳气氛中。大鼠肝微粒体在空气中和NADPH的存在下与11.8纳米摩尔氧化氯丹一起孵化，并在37°C下，有或没有0.2 mM 1,1,1-三氯丙烯-2,3-氧化物的存在下孵化15分钟。在NADPH的存在下和空气条件下，大约11%的氯化丹被代谢。当反应混合物中缺少NADPH时，没有发生代谢。当氮气代替空气时，氯化丹的降解减少了67%。在一氧化碳气氛下，没有氯化丹的代谢发生。当孵化混合物中缺少1,1,1-三氯丙烯-2,3-氧化物时，氧化氯丹被大量代谢。当其存在时，1,1,1-三氯丙烯-2,3-氧化物导致代谢的氧化氯丹数量急剧减少。作者得出结论，氯化丹的氧化降解是由肝微粒体细胞色素P-450催化的。氧化氯丹是氯化丹的氧化代谢物，通过肝环氧水合酶进一步代谢。

The metabolism of trans-chlordane (chlordane) and oxychlordane by rat liver microsomes was studied in vitro. Liver microsomes prepared from male Sprague-Dawley rats were incubated with 12.3 nmol chlordane in the presence or absence of a reduced NADPH generating system under air or atmospheres of nitrogen or carbon monoxide for 15 min at 37 degrees C. Rat liver microsomes were incubated with 11.8 nmol oxychlordane in air with NADPH and in the presence or absence of 0.2 mM 1,1,1-trichloropropene-2,3-oxide for 15 min at 37 degrees C. Approximately 11% of the chlordane was metabolized in the presence of NADPH and under air. No metabolism occurred when NADPH was absent from the reaction mixture. Degradation of chlordane was decreased by 67% when nitrogen was substituted for air. No chlordane metabolism occurred under the carbon-monoxide atmosphere. Oxychlordane was metabolized to an appreciable extent when 1,1,1-trichloropropene-2,3-oxide was absent from the incubation mixture. When present, 1,1,1-trichloropropene-2,3-oxide caused a sharp decrease in the amount of oxychlordane that was metabolized. The authors conclude that oxidative degradation of chlordane is catalyzed by hepatic microsomal cytochrome P-450. Oxychlordane, an oxidized metabolite of chlordane, is metabolized further by hepatic epoxide-hydrolase.

来源:Hazardous Substances Data Bank (HSDB)

代谢

代谢过程似乎主要是氧化性的，涉及肝脏微粒体细胞色素P-450。环氧水合酶可能是参与进一步降解环氧氯丹的主要酶，但这个过程在动物和人类中似乎进行得较慢。此外，还原脱卤作用，可能是形成反应性自由基中间体的结果，可能在氯丹的毒性中发挥重要作用。

Metabolism appears to be largely oxidative, involving hepatic microsomal cytochrome P-450. Epoxide hydrolase is probably the predominant enzyme involved in further degradation of oxychlordane, but the process appears to be slow in animals and humans. In addition, reductive dehalogenation, probably resulting in the formation of reactive free radical intermediates, may be important in the toxicity of chlordane.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氯丹分子的代谢涉及四条途径...第一种提出的代谢途径是从分子第三位羟基化开始，形成3-羟基氯丹。这一反应被认为是微粒体多功能氧化酶（MFO）系统介导的。3-羟基氯丹的脱水导致1,2-二氯氯代烯，并最终形成其他代谢物，如氧化氯丹和L-羟基-2-氯氯代烯。或者，3-羟基氯丹可能会经历氯原子被羟基取代，形成单氯二羟基和三羟基衍生物。第二条途径从脱氢氯化开始形成七氯。这一反应的机制尚未完全了解，但认为是细胞色素P-450系统和/或谷胱甘肽-S-转移酶型酶介导的。七氯的进一步代谢导致1-羟基氯代烯、七氯环氧化物，或最终形成1-氯-2,3-二羟基二氢氯丹。第三条途径从氯丹脱卤化形成L-氯二氢氯丹开始，可能由微粒体MFO系统介导。进一步的反应可能涉及水解和与葡萄糖醛酸的共轭。第四条代谢途径，也可能是最不为人所知的，涉及水解去除一个氯原子，并以其羟基取代形成L-氯-2-羟基氯丹氯醇。这一产物可能经历进一步的代谢，形成二氢氯丹的单氯二羟基和三羟基衍生物。大鼠肝脏微粒体的研究表明，细胞色素P-450可能是催化顺式氯丹降解最重要的酶。环氧化物水解酶可能是催化氧化氯丹降解的主要酶。还原脱卤，产生自由基，在氯丹的毒性中也可能很重要。

Metabolism for the chlordane molecule involves four routes ... The first proposed metabolic route starts with hydroxylation at position three of the molecule to form 3-hydroxychlordane. This reaction is thought to be mediated by the microsomal mixed-function oxidase (MFO) system. Dehydration of 3-hydroxychlordane leads to 1,2-dichlorochlordene and eventually to other metabolites such as oxychlordane and l-hydroxy-2-chlorochlordene. Alternatively, 3-hydroxychlordane may undergo replacement of chlorines by hydroxyl groups to form monochlorodihydroxylated and -trihydroxylated derivatives. The second pathway starts with dehydrochlorination to form heptachlor. The mechanism of this reaction is not completely understood but is thought to be mediated by the cytochrome P-450 system and/or by glutathione-S-transferase type enzymes. Further metabolism of heptachlor leads to 1-hydroxychlordene, heptachlor epoxide, or eventually to 1-chloro-2,3-dihydroxydihydrochlordene. The third pathway starts with dehalogenation of chlordane to form l-chlorodihydrochlordene, probably mediated by microsomal MFO systems. Further reactions probably involve hydrolysis and conjugation with glucuronic acid. The fourth metabolic pathway, and probably the least understood, involves hydrolytic removal of a chlorine atom and its replacement by a hydroxyl group to form l-chloro-2-hydroxychlordene chlorohydrin. This product may undergo further metabolism to form monochlorodihydroxy- and trihydroxy- derivatives of dihydrochlordene. Studies with rat hepatic microsomes suggest that cytochrome P-450 may be the most important enzyme to catalyze degradation of trans-chlordane. Epoxide hydrolase is probably the predominant enzyme to catalyze degradation of oxychlordane. Reductive dehalogenation, with the production of free radicals, may also be important in the toxicity of chlordane.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别：氯丹是一种氯化的环二烯类杀虫剂。氯丹是一种合成产品，工业氯丹是一种粘稠的琥珀色液体，具有刺激性氯味。它不溶于水，但溶于大多数有机溶剂，包括丙酮、环己酮、乙醇、脱臭煤油、异丙醇和三氯乙烯。氯丹是一种持久性、非系统性接触和摄入杀虫剂，具有一定的熏蒸作用。它用于陆地上对抗白蚁、甲虫、夜蛾幼虫、直翅目、地下白蚁以及许多其他害虫。它还控制家庭害虫、人类和家畜的害虫，并可作为木材防腐剂。美国所有氯丹的注册都已取消。 人类暴露：氯丹是一种中枢神经系统刺激剂。肝脏和肾脏是氯丹影响的其他器官。突然出现的抽搐之前伴有呕吐。由环二烯杀虫剂引起的癫痫可能在暴露后长达48小时出现，然后可能在初始发作后的几天内周期性地再次出现。强直-阵挛性抽搐通常伴有混乱、不协调、兴奋性，在某些情况下还会伴有昏迷、低血压和呼吸衰竭。不要给予脂肪、油或牛奶，因为这些会增强从肠道吸收。儿童、配方工人、自杀企图者、居住在用氯丹处理的住宅中的人意外中毒。有抽搐障碍史的人预计会因暴露而面临增加的风险。暴露途径包括摄入、吸入、皮肤和眼睛接触。氧氯丹是氯丹的代谢物，在母乳样本中发现。在一个孩子中，血清半衰期为88天。另一项研究确定，一个摄入含有氯丹的产品的个体的半衰期为34天。在一例急性暴露于氯丹的男性中，出现了短暂的少尿，伴有蛋白尿、血尿和轻度高血压。一名30岁的女性接触氯丹一个月后出现肌阵挛性抽搐，之前接触过氯丹出现周围性麻木、厌食、恶心和疲劳。功能障碍性出血归因于肝酶诱导和避孕药代谢增加。一名职业暴露于氯丹的男性出现了感觉异常，随后右手动和手臂抽搐。随后的事件以同样的方式开始，以强直-阵挛性癫痫发作和昏迷结束。有报道称，接触氯丹/七氯的病例与白血病和其他血液疾病有关，主要发生在家庭环境中。其他癌症的风险略有增加，包括白血病、非霍奇金淋巴瘤和软组织肉瘤以及脑癌、皮肤癌、膀胱癌和胃癌。人类细胞暴露于氯丹时没有发现致突变性。 动物/细胞研究：在4只雄性兔子的研究中，每隔4天口服给予（14）C-α和γ-氯丹的混合物，吸收良好。吸入（14）-氯丹蒸汽30分钟的 rats 保留了吸入氯丹总量的77%。在大鼠和兔子研究中，使用放射性标记的氯丹口服给药，放射性物质在组织中分布良好。无论是单次口服给药氯丹还是喂食含有该化合物的饮食，大鼠在脂肪组织、肝脏、肾脏、大脑和肌肉中保留的最高残留水平。与α异构体相比，保留了更多γ异构体。兔子氯丹的组织分布与大鼠相似。氯丹代谢缓慢。氯丹的大多数代谢物毒性较低，但氧氯丹的急性毒性更高。在大鼠的体内和体外研究中，发现了氯丹生物转化的两条途径，并显示代谢物包括反式氯丹、1,2-二氯二氯丹、氧氯丹、1-羟基-2-氯-2,3-环氧氯丹、氯丹、氯醇和1,2-反式-二羟基二氢氯丹以及七氯的代谢物。氯丹通过粪便排出。氯化烃杀虫剂通过改变神经细胞膜的电气生理和相关的酶促性质发挥作用，导致钠和钾离子通过膜的改变。干扰钙运输和Ca+2-ATP酶活性也可能涉及。环二烯化合物拮抗γ-氨基丁酸（GABA）的作用，后者诱导神经元摄取氯离子。环二烯杀虫剂阻断此活动导致神经元部分复极化，并处于不受控制的兴奋状态。氯丹和工业氯丹在小鼠和大鼠口服给药后诱导肿瘤。研究表明，在雌雄小鼠中均观察到肝细胞肿瘤的增加。在大鼠中观察到甲状腺滤泡细胞肿瘤的发生率增加。在一项研究中，观察到雄性大鼠用氯丹处理后恶性纤维组织细胞瘤的发生率增加。在一项研究中，观察到用工业级氯丹处理的雄性大鼠肝脏腺瘤的小幅增加。在动物研究中未发现致畸性。在Ames沙门氏菌微体试验中，α-氯丹和γ-氯丹未显示致突变性。氯丹未能在小鼠中引起显性致死效应。氯丹抑制了啮齿动物细胞间的间隙连接通讯，并诱导基因突变，

IDENTIFICATION: Chlordane is a chlorinated cyclodiene insecticide. Chlordane is a synthetic product, technical chlordane is a viscous amber colored liquid with a pungent chlorine like odor. It is insoluble in water but soluble in most organic solvents including acetone, cyclohexanone, ethanol, deodorized kerosene, isopropanol and trichloroethylene. Chlordane is a persistent, non-systemic contact and ingested insecticide with some fumigant action. It is used on land against formicidae, coleoptera, noctuidae larvae, saltatoria, subterranean termites and many other insect pests. It also controls household insects, pests of man and domestic animals and is a wood preservative. All U.S. registrations of chlordane have been cancelled. HUMAN EXPOSURE: Chlordane is a central nervous system stimulant. The liver and kidney are the other organs affected by chlordane. A sudden onset of convulsions preceded by vomiting. Seizures caused by cyclodiene pesticides may appear as long as 48 hr after exposure and then may reappear periodically over several days following the initial episode. Tonic-clonic convulsions usually are accompanied by confusion, incoordination, excitability and in some instances coma, hypotension and respiratory failure. Do not give fats, oils or milk since these will enhance absorption from the intestinal tract. Accidental poisoning can occur in children, formulating workers, suicide attempts, individuals who live in chlordane treated residences. Individuals with a history of convulsive disorders would be expected to be at increased risk from exposure. Routes of exposure include ingestion, inhalation, dermal and eye contact. Oxychlordane is a metabolite of chlordane was found in breast milk samples. Serum half life in one child was 88 days. Another study a half life of 34 days was determined from an individual who consumed a product containing chlordane. During an acute exposure to chlordane, a man experienced a brief episode of oliguria with proteinuria, hematuria and mild hypertension. In a 30 yr old female exposed to chlordane had myoclonic jerks after a month delay, and from previous exposure had circumoral numbness, anorexia, nausea and fatigue. Dysfunctional bleeding was attributed to hepatic enzyme induction and increased metabolism of contraceptive medicine. One man occupationally exposed to chlordane developed episodes of paresthesia and latter twitching of the right hand and arm. Additional episodes, beginning in the same way ended with grand mal seizures followed by unconsciousness. Case reports of leukemia and other blood dyscrasias have been associated with exposure to chlordane/heptachlor primarily in domestic situations/ Small excess risks for other cancers including leukemia, non-Hodgkins lymphoma and soft tissue sarcomas and cancers of the brain, skin, bladder and stomach were observed. No evidence of mutagenicity was noted in human cells exposed to chlordane. ANIMAL/CELL STUDIES: In studies on 4 male rabbits a combination of (14)C-alpha and gamma-chlordane were administered orally at 4 day intervals it was well absorbed. Rats that inhaled (14)-chlordane vapor for 30 minutes retained 77% of the total inhaled chlordane. In rat and rabbit studies using radiolabelled chlordane administered orally the radioactivity was well distributed among tissues. Rats whether being treated with a single oral dose of chlordane or fed diets containing this compound, retained the highest levels of residues in adipose tissue, liver, kidney, brain and muscle. More of the gamma isomer was retained compared to the alpha isomer. The tissue distribution of chlordane in rabbits was similar to rats. Chlordane is metabolized slowly. Most metabolites of chlordane are less toxic but oxychlordane is acutely more toxic. In vivo and in vitro studies in rats have revealed two routes of biotransformation of chlordane and shown that metabolites include trans-chlordane, 1,2-didichlorochlordene, oxychlordane, 1-hydroxy-2-chloro-2,3-epoxychlordene, chlordene, chlorohydrin and 1,2-trans-dihydroxydihydrochlordene as well as metabolites of heptachlor. Chlordane is excreted in the feces. Chlorinated hydrocarbon insecticides act by altering the electrophysiological and associated enzymatic properties of nerve cell membranes, causing a change in sodium and potassium ion flow through the membrane. Disturbances of calcium transport and Ca+2-ATPase activity may also be involved. The cyclodiene compounds antagonize the action of gamma-aminobutyric acid (GABA) which induces the uptake of chloride ions by neurons. The blockage of this activity by cyclodiene insecticides results in only partial repolarization of the neuron and a state of uncontrolled excitation. Chlordane and technical chlordane induced tumors in mice and rats after oral administration. The studies demonstrated increases of hepatocellular neoplasms in mice of both sexes. Increased incidences of thyroid follicular cell neoplasms were observed in rats treated with chlordane. An increased incidence of malignant fibrous histiocytomas was observed in one study in male rats treated wi th chlordane. A small increase in liver adenomas was seen in one study in male rats treated with technical grade chlordane. No evidence of teratogenicity was found in animal studies. Alpha-chlordane and gamma-chlordane tested in the Ames Salmonella microsome assay showed no mutagenicity. Chlordane did not cause dominant lethal effects in mice. Chlordane did inhibit gap junctional intercellular communication and induced gene mutations in rodent cells but did not induce unscheduled DNA synthesis. Chlordane did not damage bacterial or plasmid DNA. Protein deficiency has been shown to double the acute toxicity of chlordane in rats. Chlordane has shown to increase the hepatotoxic effects of carbon tetrachloride in rats.[

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：B2组可能的人类致癌物

Cancer Classification: Group B2 Probable Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

证据权重特征：根据1986年癌症风险评估指南，氯丹被归类为B2级，可能是人类致癌物。 ...人类致癌性数据：证据不足。动物致癌性数据：足够。

WEIGHT OF EVIDENCE CHARACTERIZATION: Chlordane is classified as B2, probable human carcinogen, using the 1986 Guidelines for Carcinogen Risk Assessment. ...HUMAN CARCINOGENICITY DATA: Inadequate evidence. ANIMAL CARCINOGENICITY DATA: Sufficient.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：对于氯丹和七氯对人类致癌性的证据不足。对于氯丹和七氯在实验动物中的致癌性有足够的证据。总体评估：氯丹和七氯可能对人类致癌（2B组）。

Evaluation: There is inadequate evidence in humans for the carcinogenicity of chlordane and heptachlor. There is sufficient evidence in experimental animals for the carcinogenicity of chlordane and heptachlor. Overall evaluation: Chlordane and heptachlor are possibly carcinogenic to humans (Group 2B).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3；已确认对动物有致癌性，但对人类的相关性未知。

A3; Confirmed animal carcinogen with unknown relevance to humans.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

通过皮肤吸收，更容易通过肺部，以及从... /胃肠道/ tract。

...Absorbed through skin, more readily via the lungs, and from ... /gastrointestinal/ tract.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在儿童中，脂肪浓度在单次剂量后继续上升至摄入后第8天，并且3个月后脂肪-血清分配比是1470:1。

In a child, fat concentration ... after single dose continued to rise through 8th post-ingestion day, and after 3 months fat-serum partition was 1470:1.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

主要排泄途径是胆汁，尽管几乎所有有机氯化合物都会产生可测量的尿液代谢物。许多未代谢的农药通过肠道（肠肝循环）有效地被重新吸收，从而大大减缓了粪便排泄。/固体有机氯杀虫剂/

The chief route of excretion is biliary, although nearly all organochlorines yield measurable urinary metabolites. ... Many of the unmetabolized pesticides are efficiently reabsorbed by the intestine (enterohepatic circulation) substantially retarding fecal excretion. /Solid organochlorine insecticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 接受静脉注射的Wistar大鼠 ... (14)C-α-氯丹显示，总注入活性的29%在60小时内通过粪便排出，仅有1%通过尿液排出。 /顺式异构体/

... Wistar rats that received iv ... (14)C-alpha-chlordane showed that 29% of total injected radioactivity was excreted within 60 hr in feces and only 1% was excreted in urine. /cis-isomer/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 职业暴露等级：
  C
• 职业暴露限值：
  TWA: 0.5 mg/m3 [skin]
• 危险等级：
  6.1(b)
• 立即威胁生命和健康浓度：
  100 mg/m3
• 危险品标志：
  Xn,N,Xi,F,T
• 安全说明：
  S16,S26,S33,S36,S36/37,S45,S60,S61,S7
• 危险类别码：
  R21/22,R11,R39/23/24/25,R40,R36/37/38,R50/53,R23/24/25
• WGK Germany：
  2
• 海关编码：
  29038200
• 危险品运输编号：
  2995
• RTECS号：
  PB9800000
• 包装等级：
  II
• 危险类别：
  6.1(b)

制备方法与用途

化学性质

琥珀色粘稠液体，沸点为175℃。它不溶于水但能溶解在有机溶剂中。其相对密度范围为1.59至1.63（25/4℃），折光率为nD25 1.56至1.57。该化合物在碱性溶液中容易分解，失去杀虫效果。

用途

环戊二烯类含氯杀虫剂，主要用于消灭地下害虫如蝼蛄、地老虎以及稻草害虫等，并且对于防治白蚁尤为有效。

生产方法

首先将环戊二烯用氯气氯化，在40-60℃条件下得到四氯环戊烷。接着进一步加热并通入氯气，生成多氯环戊烷。然后将其在汽化釜中气化，并与氯气在500-560℃下进行氯解，从而获得六氯环戊二烯。再将六氯环戊二烯于约55℃条件下与环戊二烯反应生成氯啶，随后在80℃左右通入氯气，则得到氯丹。

分类

农药

毒性分级

高毒

• 急性毒性：大鼠口服LD₅₀为200毫克/公斤；小鼠口服LD₅₀为145毫克/公斤

危险特性

• 与空气混合可形成爆炸性混合物
• 可燃，燃烧时产生有毒氯化物烟雾

储运特性

应储存在通风良好、低温干燥的库房中，并且需与氧化剂和食品添加剂分开存放。

灭火剂

水、泡沫灭火

职业标准

• 时间加权平均容许浓度（TWA）：0.5毫克/立方米（皮肤）
• 短时间暴露极限值（STEL）：1.5毫克/立方米（皮肤）