五氯酚 | 87-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 五氯酚
• 中文别名: 五氯苯酚
• 英文名称: Pentachlorophenol
• 英文别名: PCP；2,3,4,5,6-pentachlorophenol
• CAS: 87-86-5
• 化学式: C₆HCl₅O
• mdl: MFCD00002162
• 分子量: 266.338
• InChiKey: IZUPBVBPLAPZRR-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C
• 沸点：
  310°C (decomp)
• 密度：
  1.978
• 物理描述：
  Pentachlorophenol appears as a white crystalline solid. Slightly soluble in water. Noncombustible. Toxic by inhalation, ingestion, and skin absorption. Used as a fungicide and as a wood preservative.
• 颜色/状态：
  White monoclinic, crystalline solid
• 气味：
  Phenolic odor
• 味道：
  Taste threshold of 30 ug/L
• 溶解度：
  Soluble in most organic solvents, for example acetone 215 g/L at 20 °C. Slightly soluble in ... parafins.
• 蒸汽密度：
  9.2 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  1.10X10-4 mm Hg at 25 °C
• 亨利常数：
  2.45e-08 atm-m3/mole
• 稳定性/保质期：

  1. 该物质为白色粉末或针状结晶，可溶于稀碱溶液、乙醇、丙酮、乙醚和苯等有机溶剂，微溶于烃类，几乎不溶于水。与氢氧化钠反应生成白色结晶状的五氯酚钠。

  2. 本品具有中等毒性，空气中浓度超标时需佩戴防毒面具；操作人员应穿戴防护服并佩戴安全面罩和防化学品手套。

  有毒。经口LD₅₀对雄大鼠为146 mg/kg，对雌大鼠为175 mg/kg。该物质对皮肤有刺激性，生产场所应保持良好通风，并要求操作人员穿戴相应的防护用具。

• 自燃温度：
  Not flammable (USCG, 1999)
• 分解：
  309 °C
• 腐蚀性：
  Noncorrosive in absence of moisture
• 汽化热：
  16,742.6 gcal/gmole
• 气味阈值：
  Odor thresholds for PCP soln at 30 deg and 60 °C were 857 and 12,000 ug/l, respectively.
• 解离常数：
  pKa = 4.70
• 碰撞截面：
  135.93 Ų [M-H]-
• 保留指数：
  1731.3;1719;1753;1762;1752;1775;1720;1720;1743;1700;1751.3;1731.8;1715;1715;1749

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

... 六氯苯的主要代谢物 ... .

... Major metabolite of HCB /hexachlorobenzene/ ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

单次口服给予恒河猴五氯-(14)C-苯(0.5 mg/kg)后.../7%以五氯酚的形式在尿液中排出。

Following single oral dose of pentachloro-(14)C-benzene (0.5 mg/kg) to Rhesus monkeys ... /7% was excreted/ as pentachlorophenol ... in urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

五氯苯酚在大鼠体内和体外被脱氯成四氯和三氯对苯二酚。脱氯作用由肝微粒体酶介导，其活性可通过几种已知的细胞色素P450诱导剂预处理来增强。在人体受试者中对单次口服剂量（0.1毫克/千克）进行的药代动力学研究发现，除了五氯苯酚的葡萄糖苷酸（约12%）之外，没有检测到其他代谢物。

Pentachlorophenol ... is dechlorinated in vivo and in vitro in rat to tetra- and tri-chlorohydroquinone ... Dechlorination is mediated by liver-microsomal enzymes, and their activity is enhanced by pre-treatment with several well-known inducers of cytochrome P450 ... Pharmacokinetic study of single oral dosage (0.1 mg/kg) ... in human subjects ... revealed no metabolites were detected apart from glucuronide of PCP (about 12%).

来源:Hazardous Substances Data Bank (HSDB)

代谢

细菌分离株，与腐生性棒状细菌有关，能够以五氯苯酚作为唯一的碳源和能源进行代谢。五氯苯酚迅速被代谢成二氧化碳。在绿僵菌的培养中，五氯苯酚被甲基化形成五氯茴香醚。同样，五氯茴香醚也通过曲霉属和头花霉属的五氯苯酚形成。

Bacterial isolate, related to saprophytic coryneform bacteria, was able to metabolize pentachlorophenol as sole source of carbon and energy. Pentachlorophenol was rapidly metabolized to CO2. In cultures of Trichoderma virgatum, pentachlorophenol was methylated to form pentachloroanisole. Similarly, pentachloroanisole was formed from pentachlorophenol by Penicillium sp and Cephaloascus fragrans.

来源:Hazardous Substances Data Bank (HSDB)

代谢

五氯苯酚是六氯苯和五氯苯的人类已知代谢物。

Pentachlorophenol is a known human metabolite of HEXACHLOROBENZENE and pentachlorobenzene.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

五氯苯酚是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强大的神经毒素，低剂量时会导致过度流涎和眼泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，后者在神经和肌肉接头处释放，以允许肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动不断传输，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计成与酶的活性位点结合。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐）以及一个末端的氧。

Pentachlorophenol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

评估：对于多氯酚及其钠盐的联合暴露对人类致癌性的证据有限。...对于五氯酚对实验动物致癌性的证据是充分的。总体评估：多氯酚或其钠盐的联合暴露可能对人类具有致癌性（2B组）。/多氯酚和钠盐/

Evaluation: There is limited evidence in humans for the carcinogenicity of combined exposures to polychlorophenols and their sodium salts. ... There is sufficient evidence in experimental animals for the carcinogenicity of pentachlorophenol. Overall evaluation: Combined exposures to polychlorophenols or to their sodium salts are possibly carcinogenic to humans (Group 2B). /Polychlorophenols & sodium salts/

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

分类：B2；可能的人类致癌物 分类依据：该分类基于不充分的人类数据和充足的动物致癌性证据：在B6C3F1小鼠的一种或两种性别中，使用两种不同的五氯酚制剂，发生多种生物学上重要的肿瘤类型（肝细胞腺瘤和癌、肾上腺髓质嗜铬细胞瘤、恶性嗜铬细胞瘤和/或血管瘤）的统计学显著增加。此外，两种制剂均观察到两种不常见肿瘤（肾上腺髓质嗜铬细胞瘤和血管瘤/血管肉瘤）的高发生率。这一分类得到了诱变数据支持，这些数据表明五氯酚具有潜在的裂变能力。 人类致癌性数据：不充分。 动物致癌性数据：充足。 /基于先前的分类系统/

CLASSIFICATION: B2; probable human carcinogen BASIS FOR CLASSIFICATION: The classification is based on inadequate human data and sufficient evidence of carcinogenicity in animals: statistically significant increases in the incidences of multiple biologically significant tumor types (hepatocellular adenomas and carcinomas, adrenal medulla pheochromocytomas, and malignant pheochromocytomas, and/or hemangiomas) in one or both sexes of B6C3F1 mice using two different preparations of pentachlorophenol. In addition, a high incidence of two uncommon tumors (adrenal medulla pheochromocytomas and hemangiomas/hemangiosarcomas) was observed with both preparations. The classification is supported by mutagenicity data, which provides some indication that pentachlorophenol has clastogenic potential. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Sufficient. /Based on former classification system/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3：已确认的动物致癌物，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

本研究的目标是了解多氯联苯（PCBs）、特定羟基化多氯联苯代谢物（OH-PCBs）和五氯酚（PCP）在东部斯洛伐克出生队列的脐带血血清中的胎盘传递情况。在2002-2004年期间，从斯洛伐克东部米哈尔奥夫采和斯维德尼克/斯特罗波夫两个地区的分娩妇女中平行收集脐带血标本和母体标本。本研究选择了92对母婴标本。定量分析了4-OH-CB107、3-OH-CB153、4-OH-CB146、3'-OH-CB138、4-OH-CB187和4'-OH-CB172。脐带血清中Sigma(17)PCBs、Sigma(6)OH-PCBs和PCP的中位浓度分别为0.92、0.33和0.69 ng/g湿重，与相应母体血清水平高度相关（相关系数分别为R(2) = 0.61、0.78和0.82）。脐带与母体Sigma(17)PCBs、Sigma(6)OH-PCBs和PCP的中位比值分别为0.18、0.75和1.10。脐带血清中Sigma(6)OH-PCBs与Sigma(17)PCBs的中位比值基于湿重浓度为0.38，是母体血清中这些化合物比值的约四倍（0.09）。PCP在脐带血清中的含量比任何测量的PCB或OH-PCB同系物都要丰富。与母体相比，OH-PCB代谢物的脐带与母体比值较高，这表明要么是胎盘传递率更高，要么是胎儿相对于母体部分的代谢更多。这些发现与它们优先与能够穿越胎盘的TTR结合一致。脐带与母体的比值因同系物而异（例如，4-OH-CB107 = 0.58，4-OH-CB146 = 0.74，3'-OH-CB138 = 1.01）。

The aim of the present study was to understand the placental transfer of polychlorinated biphenyls (PCBs), specific hydroxylated PCB metabolites (OH-PCBs), and pentachlorophenol (PCP) in blood serum, in a birth cohort from eastern Slovakia. During the period 2002-2004, cord blood specimens were collected in parallel with maternal specimens from women delivering in the two eastern Slovak districts of Michalovce and Svidnik/Stropkov. A total of 92 pairs of mother-cord specimens at delivery were selected for this study. 4-OH-CB107, 3-OH-CB153, 4-OH-CB146, 3'-OH-CB138, 4-OH-CB187, and 4'-OH-CB172 were quantified. The median concentrations of Sigma(17)PCBs, Sigma(6)OH-PCBs, and PCP in cord serum were 0.92, 0.33, and 0.69 ng/g wet wt, respectively, and highly correlated with the corresponding maternal serum levels (correlations were R(2) = 0.61, 0.78, and 0.82, respectively). The median cord to mother ratios of the Sigma(17)PCBs, Sigma(6)OH-PCBs, and PCP were 0.18, 0.75, and 1.10, respectively. The median ratio of the Sigma(6)OH-PCBs to the Sigma(17) PCBs in the cord serum was 0.38 from wet wt based concn, which was about four times higher than the ratio of these compounds in maternal serum (0.09). PCP was more abundant than any PCB or OH-PCB congener measured in cord serum. The higher cord to maternal ratios of OH-PCB metabolites as compared with the parent cmpd suggests either a higher placental transfer rate or greater metabolism in the fetus as compared with the maternal compartment. These findings are consistent with their preferential binding to TTR that can cross the placenta. The cord to maternal ratio varies by congener (e.g., 4-OH-CB107 = 0.58, 4-OH-CB146 = 0.74, 3'-OH-CB138 = 1.01).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

五氯苯酚在啮齿动物、猴子和人类经口服、皮肤接触或吸入暴露后可被迅速吸收。...主要组织沉积物在不同物种之间有所差异。在死亡与五氯苯酚暴露无关的人类中，肝脏（含五氯苯酚残留量为0.067微克/克）、肾脏、大脑、脾脏和脂肪（0.013微克/克）似乎是主要的沉积部位。在小鼠中，胆囊是主要的储存部位。在大鼠中，则是肾脏。

Rapid absorption of pentachlorophenol has been reported in rodents, monkeys, & humans following oral, dermal, or inhalation exposure. ... The major tissue deposits vary somewhat between species. In humans whose deaths were not related to pentachlorophenol exposure, the liver (containing pentachlorophenol residues of 0.067 ug/g), kidney, brain, spleen, & fat (0.013 ug/g) appeared to be major deposition sites. In the mouse, the gall bladder is a principal storage site. In the rat, it is the kidney.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当测量木材处理厂工人在5个月期间暴露于五氯苯酚时，血清和尿液中五氯苯酚的水平分别是348.4至3963微克/升和41.3至760微克/升。工作场所空气中的五氯苯酚残留量在5.1至15275.1纳克/立方米之间。

When worker exposure to pentachlorophenol at wood treatment plant was measured over 5 month period, serum and urine levels ... were 348.4 to 3963 ug/L and 41.3 to 760 ug/L, respectively. Pentachlorophenol residues in workplace air were in the range of 5.1 to 15275.1 ng/cu m.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C-PCP通过皮下或腹腔注射给小鼠。大部分活性物质（72-83%）在4天内通过尿液排出；大约一半在24小时内排出；仅有微量（0.05%）通过呼出气体排出。在胆囊及其内容物、胃底壁、胃肠道内容物和肝脏中观察到高活性。

(14)C-PCP was admin to mice by sc or ip injection. Most of the activity (72-83%) was excreted in urine in 4 days; about half, in 24 hr; and only trace (0.05%), in expired air. High activity observed in gallbladder and its contents, wall of stomach fundus, contents of GI tract, and liver.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  T+,N
• 安全说明：
  S16,S22,S36/37,S45,S52,S60,S61,S7
• 危险类别码：
  R40,R36/37/38,R24/25,R26,R50/53
• WGK Germany：
  3
• RTECS号：
  SM6300000
• 海关编码：
  2908110000
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 3155 6.1/PG 2

SDS

第一部分：化学品名称

制备方法与用途

制备方法

1. 将固体氢氧化钠加入搅拌槽中，搅拌状态下加水配制成约160g/L的溶液。接着，在搅拌条件下，按六氯苯与氢氧化钠摩尔比为1∶(2.5～2.6)的比例，将六氯苯逐步加入碱液中，搅拌均匀后通过泵送入高压水解釜中。待搅拌升温至釜内压力达2.0MPa时，停止加热。由于反应放热，反应釜内温度会自动升至约230℃，同时釜内压力达到2.55MPa。保持此温度反应20分钟，水解即完成。随后泄压出料，冷却结晶、过滤即可得到鳞片状固体五氯酚钠。

2. 将上述制得的五氯酚钠加入至反应釜中，在搅拌条件下逐步加入31%的盐酸进行酸化处理，控制温度在80～90℃。待酸化完全后，产物通过水洗、过滤和干燥步骤即可获得最终产品。

3. 由三氯苯经通氯氯化得到六氯苯；随后将六氯苯与一定浓度的烧碱溶液共同加热升温，在设定的温度及压力条件下进行水解反应。反应结束后，经过冷却、结晶、过滤以及干燥过程可最终制得五氯酚钠。

合成制备方法

1. 将固体氢氧化钠加入搅拌槽中，搅拌状态下加水配制成约160g/L的溶液。接着，在搅拌条件下，按六氯苯与氢氧化钠摩尔比为1∶(2.5～2.6)的比例，将六氯苯逐步加入碱液中，搅拌均匀后通过泵送入高压水解釜中。待搅拌升温至釜内压力达2.0MPa时，停止加热。由于反应放热，反应釜内温度会自动升至约230℃，同时釜内压力达到2.55MPa。保持此温度反应20分钟，水解即完成。随后泄压出料，冷却结晶、过滤即可得到鳞片状固体五氯酚钠。

2. 将上述制得的五氯酚钠加入至反应釜中，在搅拌条件下逐步加入31%的盐酸进行酸化处理，控制温度在80～90℃。待酸化完全后，产物通过水洗、过滤和干燥步骤即可获得最终产品。

3. 由三氯苯经通氯氯化得到六氯苯；随后将六氯苯与一定浓度的烧碱溶液共同加热升温，在设定的温度及压力条件下进行水解反应。反应结束后，经过冷却、结晶、过滤以及干燥过程可最终制得五氯酚钠。