2,3,4-三溴苯酚 | 138507-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,3,4-三溴苯酚
• 英文名称: 2,3,4-tribromo-phenol
• 英文别名: 2,3,4-tribromophenol；2,3,4-Tribrom-phenol；tribromophenol；Phenol, tribromo-
• CAS: 138507-65-0
• 化学式: C₆H₃Br₃O
• 分子量: 330.801
• InChiKey: OUCSIUCEQVCDEL-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  302.5±37.0 °C(Predicted)
• 密度：
  2.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 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

单次口服给药14C 1,2-双(2,4,6-三溴苯氧基)乙烷(BTBPE)给常规和大胆管插管的雄性Sprague-Dawley大鼠。确定了组织的分布、排泄和代谢。BTBPE是一种低体积的溴化阻燃剂，用于树脂或塑料，同行评审期刊中的毒性数据非常有限。BTBPE在亲脂性溶液中相当不溶，这使得剂量制备变得困难。大部分的14C (>94%)在72小时内通过两组大鼠的粪便排出，组织保留最少。亲脂性组织含有最高浓度的BTBPE，例如胸腺、脂肪组织、肾上腺、肺和皮肤。代谢物通过尿液、胆汁和粪便排出，但水平非常低。粪便中的代谢物被定性为单一羟基化、单一羟基化并脱溴、在单个芳香环上的二羟基化/脱溴、每个芳香环上的单一羟基化并伴有脱溴，以及醚键两侧的断裂以产生三溴酚和三溴苯氧基乙醇...

A single oral dose of (14)C 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) was administered to conventional and bile-duct cannulated male Sprague-Dawley rats. Tissue disposition, excretion and metabolism was determined. BTBPE is a low-volume brominated flame retardant used in resins or plastics, and toxicity data in peer-reviewed journals is extremely limited. BTBPE was fairly insoluble in lipophilic solutions, which made dose preparation difficult. The great majority of (14)C (>94%) was excreted in the feces of both groups of rats at 72 hr, and tissue retention was minimal. Lipophilic tissues contained the highest concentrations of BTBPE, e.g. thymus, adipose tissue, adrenals, lung, and skin. Metabolites were excreted in the urine, bile and feces, but at a very low level. Fecal metabolites were characterized as monohydroxylated, monohydroxylated with debromination, dihydroxylated/debrominated on a single aromatic ring, monohydroxylated on each aromatic ring with accompanying debromination, and cleavage on either side of the ether linkage to yield tribromophenol and tribromophenoxyethanol...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者身体前倾或将其置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/替代和体外测试/ 全反式维甲酸诱导分化及未分化的SH-SY5Y人神经母细胞瘤细胞培养暴露于一系列浓度的三溴苯酚，持续24、48和72小时，并在形态学、基础细胞毒性和生化水平上评估其效果。通过总蛋白含量的定量评估，神经母细胞瘤细胞数量随着三溴苯酚浓度的增加和暴露时间的延长而逐渐受到抑制。根据平均有效浓度，分化培养物比未分化细胞敏感近三倍。通过中性红摄取评估的溶酶体功能在未分化细胞中受到刺激。所有处理均刺激了MTS代谢，尤其在24小时时分化细胞的作用更为显著。乙酰胆碱酯酶活性随着未分化细胞暴露时间的延长而增加，而在分化细胞中，24小时时的活性增加了一倍。从12.5微摩尔开始，形态学改变明显，表现为水样变性和细胞数量的减少，从该浓度开始，还观察到细胞核固缩和凋亡小体。总之，三溴苯酚的主要效果是诱导神经母细胞瘤细胞分化，表现为细胞生长的抑制和乙酰胆碱酯酶活性的增加，临界细胞浓度为0.1微摩尔。在高浓度下观察到凋亡。诱导细胞分化和分化细胞的特殊敏感性可以解释三溴苯酚在胚胎毒性和胎儿毒性潜力中涉及的一些机制。

/ALTERNATIVE and IN VITRO TESTS/ Retinoic acid differentiated and non-differentiated SH-SY5Y human neuroblastoma cell cultures were exposed to a range of concentrations of tribromophenol for 24, 48 and 72 hr and the effects evaluated at morphological, basal cytotoxicity and biochemical levels. Neuroblastoma cell number, evaluated by quantification of total protein content, was increasingly inhibited in accordance with the concentration of tribromophenol and the exposure time period. According to the mean effective concentrations, differentiated cultures were nearly three times more sensitive than naive cells. Lysosomal function evaluated by the neutral red uptake was stimulated, particularly in non-differentiated cells. MTS metabolism was stimulated by all the treatments, with more potency at 24 h for differentiated cells. Acetylcholinesterase activity increased with the time of exposure in non-differentiated cells, while in differentiated cells the activity was doubled at 24 hr. Morphological alterations were evident from 12.5 uM, showing hydropic degeneration and reduction in cell number, and from that concentration, piknosis and apoptotic bodies were observed. In conclusion, the main effects detected for tribromophenol were the induction of neuroblastoma cell differentiation, as expressed by the inhibition of cell growth and the increase in acetylcholinesterase activity with a critical cell concentration of 0.1 uM. Apoptosis was observed at high concentrations. The induction of cell differentiation and the special sensitivity of differentiated cells can explain some mechanisms involved in the embryotoxic and fetotoxic potential of tribromophenol.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

遗传毒性：在短期处理中，三溴苯酚在0.050毫克/毫升和0.10毫克/毫升的剂量下，无论是否具有代谢激活系统，都引起了结构性的染色体畸变。没有诱导多倍体。在短期处理中，较高两个剂量的细胞结构性染色体畸变明显增加，无论是否具有代谢激活（频率分别为：0.050毫克/毫升时为10.5%，0.10毫克/毫升时为23.5%）。没有诱导多倍体。在短期处理中，无代谢激活时的0.050毫克/毫升和有代谢激活时的0.10毫克/毫升观察到了细胞遗传学效应。

/GENOTOXICITY/ In the short-term treatment, /tribromophenol/ induced structural chromosomal aberration at doses of 0.050 mg/mL and 0.10 mg/mL, with and without metabolic activation systems. No polyploidy was induced. Cells with structural chromosomal aberrations were apparently increased at the two higher doses in the short-term treatment with and without metabolic activation (frequencies: 10.5 % at 0.050 mg/mL and 23.5 % at 0.10 mg/mL). Polyploidy was not induced. Cytogenetic effects were observed at 0.050 mg/mL in the short-term treatment without metabolic activation and at 0.10 mg/mL in the short-term treatment with metabolic activation.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

三溴苯酚在雄性和雌性Holzman白化大鼠体内的吸收、分布和消除进行了研究，在大鼠单次口服给药剂量从4.04到5.34 mg/kg后。三溴苯酚在大鼠体内迅速被吸收。大部分放射性物质（77%）通过尿液迅速排出，2%到14%在48小时内通过粪便排出。这种物质在大鼠体内的药代动力学似乎遵循一个室开放模型系统。

... The absorption, distribution, and elimination of /tribromophenol/ were examined in male or female Holzman albino rats after a single oral administration at doses from 4.04 to 5.34 mg/kg. /Tribromophenol/ was rapidly absorbed in rats. The bulk of the radioactivity (77 %) was readily excreted via urine and 2 to 14 % were eliminated in the feces, within 48 hours. The pharmacokinetics of this substance in rats appeared to follow a one compartment open model system.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  2,3,4-三溴苯酚 在 氢氧化钾 、 硝酸 作用下， 生成 2,3,4-tribromo-6-nitro-anisole
  参考文献：
  名称：

  Kohn; Strassmann, Monatshefte fur Chemie, 1924, vol. 45, p. 601

  摘要：

  DOI：
• 作为产物：
  描述：

  间溴苯酚 在 溴 、 溶剂黄146 作用下， 反应 3.0h， 生成 2,3,4-三溴苯酚
  参考文献：
  名称：

  多溴联苯醚（BDE）；制备参考标准品和氟化内部分析标准品

  摘要：

  四个新的二氟化四-和五溴用于GC-MS / GC-ECD分析BDE内部标准，2F - BDE 47，2F - BDE 85，2F - BDE 99和2F - BDE 119，已经在纯度98-99.0％制备主要由新tribromodifluorophenols（耦合19 - 21）和对称bromodiphenyliodonium盐（8，22）。四种二氟化BDEs作为定量BDE分析的内标物显示出令人鼓舞的特性。四溴，五溴，六溴和七溴BDE参考标准品，BDE 75，BDE 85，BDE 138和BDE 183的纯度也达到98.4％至99.8％。

  DOI：

  10.1016/j.tet.2006.01.092

文献信息

• [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。
• AZOLE DERIVATIVE, INTERMEDIATE COMPOUND, METHOD FOR PRODUCING AZOLE DERIVATIVE, AGRICULTURAL OR HORTICULTURAL CHEMICAL AGENT, AND PROTECTIVE AGENT FOR INDUSTRIAL MATERIAL
  申请人：Kureha Corporation

  公开号：US20200288714A1

  公开（公告）日：2020-09-17

  It is provided a plant disease controlling agent having low toxicity to human and animals and excellent handling safety, and showing excellent controlling effects on various plant diseases and high antibiotic action to plant disease germs. A compound represented by the following the general formula (I), or an N-oxide or agrochemically acceptable salt thereof.

  提供一种植物病害控制剂，对人类和动物毒性低，具有出色的操作安全性，在各种植物病害上显示出优秀的控制效果，并对植物病原菌具有高抗生素作用。 由以下一般式（I）表示的化合物，或其N-氧化物或农药可接受的盐。
• [EN] MICROBIOCIDAL QUINOLINE (THIO)CARBOXAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS MICROBIOCIDES DE QUINOLÉINE (THIO)CARBOXAMIDE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2019053010A1

  公开（公告）日：2019-03-21

  Compounds of the formula (I) wherein the subsitiuents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

  式(I)中的化合物，其中取代基如权利要求1所定义。此外，本发明涉及包括式(I)化合物的农药组合物，制备这些组合物以及在农业或园艺中使用这些化合物或组合物来对抗、预防或控制植物、收获的农作物、种子或非生物材料受植物病原微生物，特别是真菌的侵害。
• [EN] MICROBIOCIDAL ANILIDE DERIVATIVES<br/>[FR] DÉRIVÉS D'ANILIDES MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017076982A1

  公开（公告）日：2017-05-11

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

  式（I）中的化合物，其中取代基如权利要求1中定义的那样，可用作杀虫剂，尤其是杀真菌剂。
• [EN] FUNGICIDAL COMPOSITIONS<br/>[FR] COMPOSITIONS FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2018219773A1

  公开（公告）日：2018-12-06

  A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

  一种含有成分（A）和（B）混合物的杀菌组合物，其中成分（A）和（B）如权利要求1中所定义，以及将该组合物用于农业或园艺中，用于控制或预防植物被植物病原微生物，尤其是真菌的侵害。