五氯酚钠 | 131-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 五氯酚钠
• 中文别名: 1,2,3,4,5-五氯酚钠；五氯苯酚钠
• 英文名称: sodium pentachlorphenate
• 英文别名: sodium pentachlorophenate；sodium pentachlorophenolate；pentachlorophenol sodium salt；sodium pentachlorophenoxide；sodium pentachlorophenol；sodium salt of pentachlorophenol；pentachlorophenate sodium salt；Natrium-pentachlorphenolat；sodium;2,3,4,5,6-pentachlorophenolate
• CAS: 131-52-2
• 化学式: C₆Cl₅O*Na
• 分子量: 288.32
• InChiKey: HCJLVWUMMKIQIM-UHFFFAOYSA-M

物化性质

• 稳定性/保质期：
  1. 水溶液呈弱碱性，加酸酸化至pH 6.8-6.6时，全部析出为五氯酚。受日光照射易分解，干燥时性质稳定，有特殊气味。 2. 空气中浓度超标时，必须佩戴防毒口罩。操作人员应穿防酸碱工作服、戴防化学品手套，必要时戴安全防护眼镜。尽可能减少与本品直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

PCP或其钠盐的主要代谢过程降解如下：(a)甲基化生成PCP的甲基醚，五氯茴香醚；(b)羟基的酰化反应生成五氯苯酚醋酸酯；(c)脱氯生成四氯酚；以及(d)羟基化生成四氯二羟基苯。这些初始步骤产生的代谢物会进一步转化... 因此，可能会产生许多物质，它们的积累程度各不相同；限速步骤是环裂解，形成如四氯丁二酸等氯代脂肪族化合物。进一步的脱氯可能会导致脂肪族化合物的进一步转化，形成低分子物质，如乙酸或琥珀酸，然后它们进入三羧酸循环。

The major metabolic processes degrading PCP or its sodium salt are as follows: (a)methylation to yield the methylether of PCP, pentachloroanisole; (b)acylation of the hydroxyl group resulting in pentachlorophenol acetate; (c)dechlorination to tetrachlorophenols; and(d)hydroxylation to tetrachlorodihydroxybenzenes. The metabolites originating from these initial steps are subject to further transformations... Thus, a number of substances may arise, which accumulate to different extents; the limiting step is the ring fission to chlorinated aliphatic compounds such as tetrachloromuconic acid. Further dechlorination may result in further transformations of the aliphatic compounds to form low molecular substances such as acetic acid or succinate, which then enter the tricarboxylic acid cycle.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在口服五氯苯酚的兔尿液中发现了五氯苯酚钠β-葡萄糖苷酸和氯醌。在给小鼠腹腔注射2小时后，在内脏器官中也观察到了氯醌。

In urine of rabbit orally admin pentachlorophenol, pentachlorophenyl sodium beta-glucuronide and chloranil were found. Chloranil was also observed in internal organs of mice 2 hr after ip injection.

来源:Hazardous Substances Data Bank (HSDB)

代谢

五氯苯酚在辣根中产生八氯联苯醌。/来自表格；五氯苯酚/

Pentachlorophenol yields octachlorobiphenylquinone in horseradish. /From table; pentachlorophenol/

来源:Hazardous Substances Data Bank (HSDB)

代谢

未改变的五氯苯酚会通过兔、大鼠、小鼠和猴的尿液排出。除了游离的五氯苯酚外，大鼠还会排出四氯-p-羟基醌和三氯-p-羟基醌。这两种代谢物以及母化合物都会以游离形式和葡萄糖苷酸形式排出。/五氯苯酚/

Unchanged pentachlorophenol is excreted in the urine of rabbit, rat, mouse, and monkey. In addition to free pentachlorophenol, rats excrete tetrachloro-p-hydroquinone and trichloro-p-hydroquinone. ... Both metabolites as well as the parent cmpd are excreted free and as glucuronides. /Pentachlorophenol/

来源:Hazardous Substances Data Bank (HSDB)

代谢

从成年Sprague Dawley大鼠分离的肝细胞与纯度为99%的分析级五氯苯酚、工业级五氯苯酚或其仅含有少量工业杂质的钠盐一起培养。工业级五氯苯酚以浓度依赖性的方式显著诱导单加氧酶活性，在浓度为30至50微摩尔时，最大反应约为14倍。暴露于50微摩尔工业级五氯苯酚钠盐后，单加氧酶诱导作用较小，仅2.7倍，而在暴露于50微摩尔分析级五氯苯酚后，几乎检测不到。任何一种五氯苯酚制剂的预处理均等程度地抑制了单加氧酶产物的二期代谢。通过培养液中乳酸脱氢酶的泄漏来评估的细胞膜损伤，也观察到了所有测试的五氯苯酚制剂。这些结果表明，单加氧酶诱导可归因于工业杂质，而细胞毒性效应是由五氯苯酚本身引起的。作者得出结论，测量培养的大鼠肝细胞中单加氧酶活性可能提供了一种检测复杂工业化学品中作为杂质存在的酶诱导剂的方法。/五氯苯酚/

Hepatocytes isolated from adult Sprague Dawley rats were incubated with analytical pentachlorophenol of 99% purity, technical grade pentachlorophenol, or its sodium salt, whic contains only minor concn of technical impurities. Monooxygenase activity was markedly induced by technical grade pentachlorophenol in a concn dependent pattern, with a maximum response of approx 14 fold seen at concn of 30 to 50 umol. Monooxygenase induction was much less marked after exposure to 50 umol sodium salt of technical grade pentachlorophenol, only 2.7 fold, and was barely detectable after exposure to 50 umol analytical pentachlorophenol. Phase II metabolism of monooxygenase product was equally inhibited by pretreatment with any of the pentachlorophenol preparations. Cell membrane damage, assessed by leakage of lactate dehydrogenase into the culture medium, was also observed with all the pentachlorophenol preparations tested. These results indicated that monooxygenase induction was attributable to technical impurities, while cytotoxic effects were caused by the pentachlorophenol itself. The authors conclude that the measurement of monooxygenase activity in cultured rat hepatocytes may provide a method of detecting enzyme inducers as contaminants in complex industrial chemicals. /Pentachlorophenol/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

来源:ILO International Chemical Safety Cards (ICSC)

毒理性

• 吸入症状

咳嗽。喉咙痛。请参阅摄入。

Cough. Sore throat. See Ingestion.

来源:ILO International Chemical Safety Cards (ICSC)

毒理性

• 皮肤症状

可能会被吸收！红色。疼痛。进一步见吸入。

MAY BE ABSORBED! Redness. Pain. Further see Inhalation.

来源:ILO International Chemical Safety Cards (ICSC)

毒理性

• 眼睛症状

红肿。疼痛。

Redness. Pain.

来源:ILO International Chemical Safety Cards (ICSC)

毒理性

• 摄入症状

发热。出汗。不协调。呼吸急促。呼吸困难。无力。头痛。恶心。呕吐。腹痛。眩晕。嗜睡。

Fever. Sweating. Incoordination. Shortness of breath. Laboured breathing. Weakness. Headache. Nausea. Vomiting. Abdominal pain. Dizziness. Drowsiness.

来源:ILO International Chemical Safety Cards (ICSC)

吸收、分配和排泄

... 在那些曾接触过五氯苯酚和钠盐混合物的死者肝脏、血液和尿液中发现了五氯苯酚。

... Pentachlorophenol was found in the liver, blood, and urine /of those fatalities who had been exposed to pentachlorophenol and sodium salt mixture/.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

兔子口服等效于94毫克五氯酚的氯五氯酚钠24小时后组织分布：尿液和粪便70.6%；胃和肠道6.76%；肌肉6.42%；皮肤2.22%；血液1.90%；肝脏和胆囊0.743%；肾脏0.267%；心脏、肺和睾丸0.171%；中枢神经系统0.096%。/来自表格/

Distribution in tissues of rabbit 24 hr after 1 oral dose of sodium pentachlorophenate equiv to 94 mg of pentachlorophenol: urine & feces 70.6% stomach & intestine 6.76%; muscle 6.42%; skin 2.22%; blood 1.90%; liver & gallbladder 0.743%; kidneys 0.267%; heart, lung & testes 0.171%; cns 0.096%. /From table/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

根据大鼠单次暴露于戊氯酚钠盐气溶胶的半衰期，戊氯酚的体内负担在多达5天的每日暴露后并未增加。结果表明，先前的暴露增加了动物消除化合物的能力。排泄似乎不足以解释观察到的效果。

... Based on the half-life following a single exposure of rats to an aerosol of the sodium salt, the body burden of pentachlorophenol did not increase following as many as 5 daily exposures. The results suggested that prior exposure increased the ability of animals to eliminate the cmpd. Excretion seemed insufficient to account for observed effect.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

五氯苯酚可以通过皮肤和胃肠道被吸收。每两只兔子中有一只被口服给予五氯苯酚钠盐的水溶液（0.25%），相当于每千克37毫克五氯苯酚……在给予的五氯苯酚量中，分别回收了92%和91%。大部分物质在尿液中找到，分别约有4%和7%存在于胃肠道中。其余部分在组织中均匀分布。在……兔子的尿液中，只有极少量的五氯苯酚以结合形式排出。/五氯苯酚/

Pentachlorophenol ... can be absorbed through skin & from GI tract. Each /of 2 rabbits/ was given 1 oral dose of sodium salt (0.25% aq soln) equivalent to 37 mg pentachlorophenol/kg ... of the admin quantities of pentachlorophenol, 92 & 91%, respectively, were recovered. Bulk of the material was found in urine & about 4 & 7%, respectively, were present in GI tract. Remainder was well distributed throughout the tissues. Only traces of pentachlorophenol are excreted in conjugated form in the urine of the ... rabbit. /Pentachlorophenol/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  储存于通风、低温、干燥的库房内，并与其他氧化剂和食品添加剂分开存放。

制备方法与用途

制备方法

1. 由六氯苯水解制得。
2. 在三氯苯中通入氯气进行氯化，生成六氯苯，再与一定浓度的烧碱溶液加热升温，在特定温度和压力下进行水解。反应产物经冷却、结晶、过滤和干燥后即可得到所需产品。
3. 利用六六六无效体为原料，通过高压水解制得五氯酚钠。具体步骤如下：先配制160g/L的氢氧化钠溶液，并按六氯苯与氢氧化钠摩尔比1:(2.5～2.6)的比例加入六氯苯，搅拌均匀后送入水解釜中。当搅拌升温至压力达到2MPa时停止加热，利用反应热使压力升至2.55MPa（相应温度为230℃），保持近20分钟后完成水解。随后卸压出料并冷却结晶，即可得到产品。

合成制备方法

1. 由六氯苯水解制得。
2. 在三氯苯中通入氯气进行氯化，生成六氯苯，再与一定浓度的烧碱溶液加热升温，在特定温度和压力下进行水解。反应产物经冷却、结晶、过滤和干燥后即可得到所需产品。

反应信息

• 作为反应物：
  描述：

  五氯酚钠 在 盐酸 作用下， 生成 五氯酚
  参考文献：
  名称：

  Cyclohexane extraction to remove chlorodibenzo-p-dioxins

  摘要：

  从至少含有一种氯代二苯并对二氧杂环戊烷杂质的多氯苯中去除氯代二苯并对二氧杂环戊烷的方法包括：制备多氯苯的水溶性碱性盐的水溶液，将水溶液与环己烷混合以从中提取二氧杂环戊烷，从环己烷相中倾倒纯化后的水溶液，对纯化后的水溶液进行中和以沉淀纯化后的多氯苯，并分离沉淀物。

  公开号：

  US04228309A1
• 作为产物：
  描述：

  五氯酚 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 五氯酚钠
  参考文献：
  名称：

  一种制备五氯酚钠液体产品的方法

  摘要：

  本发明公开了一种五氯酚钠液体产品的制备方法，包括以下步骤：苯酚与氯气发生氯氢取代反应，生成五氯酚熔融液；五氯酚熔融液经过水碎形成多空沙粒状五氯酚固体；五氯酚固体与氢氧化钠溶液发生中和反应，生成五氯酚钠粗溶液；用水对五氯酚钠粗溶液进行浓度调制，然后灌装成五氯酚钠液体产品。本发明的五氯酚钠液体产品制备方法，省去了蒸发、结晶、离心脱水三个工艺，节约了电量、天然气量和水量，且操作过程不会有刺激性气体溢出，过程安全可控，可完全实现自动化，生产效率显著提高，生产成本显著降低。

  公开号：

  CN105248415A
• 作为试剂：
  描述：

  CBZ-L-缬氨酸 、 甘氨酸乙酯盐酸盐 在 五氯酚钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以14%的产率得到1--1,3-dicyclohexyl-harnstoff
  参考文献：
  名称：

  Izdebski, Jan, Polish Journal of Chemistry, 1988, vol. 62, # 1-3, p. 297 - 300

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。

表征谱图