2,6-二溴-4-[1-(3-溴-4-羟苯基)-1-甲基乙基]苯酚 | 6386-73-8

• 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: 2,6-二溴-4-[1-(3-溴-4-羟苯基)-1-甲基乙基]苯酚
• 英文名称: 2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
• 英文别名: 2,6-dibromo-4-[2-(3-bromo-4-hydroxyphenyl)propan-2-yl]phenol；tribromobisphenol A；3,3',5-Tribromobisphenol A
• CAS: 6386-73-8
• 化学式: C₁₅H₁₃Br₃O₂
• 分子量: 464.979
• InChiKey: WYBOEVJIVYIEJL-UHFFFAOYSA-N

物化性质

• 熔点：
  107-110 °C
• 沸点：
  413.1±40.0 °C(Predicted)
• 密度：
  1.873±0.06 g/cm3(Predicted)
• 折光率：
  Index of refraction = 1.656[GuideChem; CAS No. 6386-73-8 (Phenol,2,6-dibromo-4-
• 解离常数：
  pKa = 7.80

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

四溴双酚A（TBBPA）通过腹腔注射（IP）给予大鼠高剂量单次给药后，能够迅速吸收进入血液，分布到体内器官，并最终被排出体外。在给药后的72小时内，大约51-65%的给予的14C标记剂量通过粪便排出，只有极少量（0.3%）通过尿液排出。粪便中的14C活动被鉴定为TBBPA（大约90%）和三溴双酚A（大约10%）。血液或器官中的14C活动的身份尚未确定。

TBBPA /tetrabromobisphenol A/ administered /to rats/ IP in high, single doses was readily absorbed into the blood, distributed in body organs and eliminated. During 72 hr following administration, 51-65% of the given (14)C-dose was excreted in feces, only a slight amount (0.3%) in the urine. The (14)C activity in feces was identified as TBBPA (approximately 90%) and tribromobisphenol A (approximately 10%). The identity of (14)C-activity in blood or organs was not determined.

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毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，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。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，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。寻求医疗帮助。 /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……。预期癫痫发作，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）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，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……。/毒物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"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（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

内分泌调节/四溴双酚A（TeBBPA）是双酚A（BPA）的一种四元溴化变体，是全球最常用的溴化阻燃剂之一。/作者/比较了TeBBPA、BPA及其溴化类似物单-(MBBPA)、二-(DBBPA)和三溴双酚A（TrBBPA）在雌激素依赖性人类乳腺癌细胞系MCF-7中的雌激素效力。所有化合物都与17beta-雌二醇竞争结合雌激素受体，尽管测试化学物质对雌激素受体的亲和力远低于17beta-雌二醇。与在无血清培养基中孵化相比，TrBBPA和TeBBPA在100%血清中孵化时对完整MCF-7细胞内的雌激素受体的可及性明显降低，表明它们与血清蛋白有很强的结合。BPA、MBBPA和DBBPA对受体的可及性仅略有降低。所有测试化合物都能诱导MCF-7细胞的增殖，随着溴代取代基数量的增加，潜力降低。TeBBPA没有诱导最大细胞生长，表明在高浓度下具有细胞毒性。BPA及其溴化类似物（TeBBPA除外）诱导孕酮受体和pS2的能力与17beta-雌二醇相当，尽管所需浓度更高。/这些/研究表明，与17beta-雌二醇相比，BPA及其溴化类似物对所有测试终点的雌激素效力要低得多，TeBBPA是最不具有雌激素性的化合物。

/ENDOCRINE MODULATION/ Tetrabromobisphenol A (TeBBPA) is a four-meta-brominated variant of bisphenol A (BPA) and is one of the most commonly used brominated flame retardants worldwide. /The authors/ compared the estrogenic potency of TeBBPA, BPA and the brominated analogs mono- (MBBPA), di- (DBBPA), and tribromobisphenol A (TrBBPA) in the estrogen-dependent human breast cancer cell line MCF-7. All of the compounds competed with 17beta-estradiol for binding to the estrogen receptor, although the affinity of the test chemicals to the estrogen receptor was much lower than that of 17beta-estradiol. TrBBPA and TeBBPA showed a considerably lower access to the estrogen receptors within intact MCF-7 cells incubated in 100% serum compared to incubation in serum-free medium, indicating a strong binding to serum proteins. BPA, MBBPA, and DBBPA showed only a slightly reduced access to the receptors. All of the test compounds induced proliferation in MCF-7 cells, the potential decreasing with increasing number of bromo-substitutions. TeBBPA did not induce maximal cell growth, indicating cytotoxic effects at high concentrations. BPA and the brominated analogs, except TeBBPA, induced progesterone receptor and pS2 to the same extent as 17beta-estradiol, although at much higher concentrations. /These/ studies demonstrate that compared to 17beta-estradiol, BPA and the brominated analogs have much lower estrogenic potencies for all of the endpoints tested, TeBBPA being the least estrogenic compound.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

内分泌调节/ 作者们/研究了溴代酚和酚类化合物的影响，其中一些是溴代阻燃剂，它们对纯化的非洲爪蟾甲状腺转运蛋白（xTTR）和非洲爪蟾甲状腺激素受体β的配体结合域（xTR LBD）与（125）I-3,3',5-L-三碘甲状腺原氨酸（（125）I-T(3)）的结合，以及对重组非洲爪蟾细胞系（XL58-TRE-Luc）中T(3)反应性报告基因的诱导，以及对非洲爪蟾蝌蚪T(3)诱导或自发的变态作用。在测试的溴代酚和酚类化合物中，3,3',5-三溴双酚A和3,3'-二溴双酚A分别是与xTTR和xTR LBD结合的（125）I-T(3)最有力的竞争者。在与羟基相邻的位置上有溴原子的结构更有效地与T(3)结合到xTTR和xTR LBD竞争。3,3',5-三溴双酚A和3,3',5,5'-四溴双酚A在0.1-1.0 uM的浓度下，在T(3)反应性报告基因分析中表现出T(3)激动剂和拮抗剂的活性。从牛胎儿和牛蛙蝌蚪获得的血清减弱了3,3',5-三溴双酚A的T(3)激动剂和拮抗剂活性，但没有减弱o-t-丁基酚的T(3)拮抗剂活性，因为xTTR对其没有显著的亲和力。在非洲爪蟾蝌蚪的体内短期基因表达分析中，使用内源性T(3)反应性基因作为分子标记，证实了0.5 uM 3,3',5-三溴双酚A的T(3)激动剂和拮抗剂活性。...结果表明，3,3',5-三溴双酚A影响T(3)与xTTR和xTR的结合，并且干扰细胞内T(3)信号传导途径。

/ENDOCRINE MODULATION/ /The authors/ investigated the effects of the brominated phenolic and phenol compounds, some of which are brominated flame retardants, on the binding of (125)I-3,3',5-L-triiodothyronine ((125)I-T(3)) to purified Xenopus laevis transthyretin (xTTR) and to the ligand-binding domain of X. laevis thyroid hormone receptor beta (xTR LBD), on the induction of a T(3)-responsive reporter gene in a recombinant X. laevis cell line (XL58-TRE-Luc) and on T(3)-induced or spontaneous metamorphosis in X. laevis tadpoles. Of the brominated phenolic and phenol compounds tested, 3,3',5-tribromobisphenol A and 3,3'-dibromobisphenol A were the most potent competitors of (125)I-T(3) binding to xTTR and the xTR LBD, respectively. Structures with a bromine in either ortho positions with respect to the hydroxy group competed more efficiently with T(3) binding to xTTR and the xTR LBD. 3,3',5-Tribromobisphenol A and 3,3',5,5'-tetrabromobisphenol A, at 0.1-1.0 uM, exerted both T(3) agonist and antagonist activities in the T(3)-responsive reporter gene assay. Sera obtained from fetal bovine and bullfrog tadpoles weakened the T(3) agonist and antagonist activities of 3,3',5-tribromobisphenol A, but not the T(3) antagonist activity of o-t-butylphenol, for which xTTR has no significant affinity. The T(3) agonist and antagonist activities of 0.5 uM 3,3',5-tribromobisphenol A were confirmed in the in vivo, short-term gene expression assay in premetamorphic X. laevis tadpoles using endogenous, T(3)-responsive genes as molecular markers. ...Results suggest that 3,3',5-tribromobisphenol A affects T(3) binding to xTTR and xTR and that it interferes with the intracellular T(3) signaling pathway.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  9
• 海关编码：
  2908199090
• 包装等级：
  II
• 危险品运输编号：
  UN 3152

反应信息

• 作为反应物：
  描述：

  2,6-二溴-4-[1-(3-溴-4-羟苯基)-1-甲基乙基]苯酚 在 ruthenium trichloride 、 sodium periodate 、 硫酸 、 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 3-(2-bromo-4-(2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl)phenoxy)propane-1,2-diol
  参考文献：
  名称：

  卤化双酚单取代醚的合成和毒性：为新兴污染物的潜在环境转化产物建立库

  摘要：

  作为卤代双酚类化合物的一个重要分支，卤代双酚单取代醚类化合物因其毒性和变异性在环境健康科学中受到了广泛关注。在本研究中，开发了一种双酚单取代醚副产物库的合成方法。通过使用通用且高效的方法，四氯双酚 A、四溴双酚 A 和四溴双酚 S 单取代烷基醚化合物的产率为 39-82%。随后，使用三种不同的细胞系（HepG2、小鼠原代星形胶质细胞和 Chang 肝细胞）筛选了 27 种化合物的细胞毒性。化合物2,6-二溴-4-[3,5-二溴-4-(2-羟基乙氧基)苯-1-磺酰基]苯酚在各种细胞中比其他化合物毒性更大，并且该化合物对正常肝细胞和癌细胞的敏感性不一致。化合物 2,6-dichloro-4-(2-{3,5-dichloro-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol 和 2,6- dibromo-4-(2-{3,5-dibromo-4-[(

  DOI：

  10.1002/cbdv.202000481
• 作为产物：
  描述：

  双酚A 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到2,6-二溴-4-[1-(3-溴-4-羟苯基)-1-甲基乙基]苯酚
  参考文献：
  名称：

  卤化双酚单取代醚的合成和毒性：为新兴污染物的潜在环境转化产物建立库

  摘要：

  作为卤代双酚类化合物的一个重要分支，卤代双酚单取代醚类化合物因其毒性和变异性在环境健康科学中受到了广泛关注。在本研究中，开发了一种双酚单取代醚副产物库的合成方法。通过使用通用且高效的方法，四氯双酚 A、四溴双酚 A 和四溴双酚 S 单取代烷基醚化合物的产率为 39-82%。随后，使用三种不同的细胞系（HepG2、小鼠原代星形胶质细胞和 Chang 肝细胞）筛选了 27 种化合物的细胞毒性。化合物2,6-二溴-4-[3,5-二溴-4-(2-羟基乙氧基)苯-1-磺酰基]苯酚在各种细胞中比其他化合物毒性更大，并且该化合物对正常肝细胞和癌细胞的敏感性不一致。化合物 2,6-dichloro-4-(2-{3,5-dichloro-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol 和 2,6- dibromo-4-(2-{3,5-dibromo-4-[(

  DOI：

  10.1002/cbdv.202000481

文献信息

• The UV/Fenton Degradation of Tetrabromobisphenol A Catalyzed by Nanocrystalline Chromium Substituted Magnetite
  作者：Yuanhong Zhong、Xiaoliang Liang、Zisen He、Wei Tan、Hongping He、Runliang Zhu、Yin Zhong、Jianxi Zhu、Peng Yuan、Zheng Jiang

  DOI：10.1166/jnn.2014.8967

  日期：2014.9.1

  The heterogeneous UV/Fenton degradation of tetrabromobisphenol A (TBBPA) catalyzed by nanocrystalline Fe3O4 and Fe2.04Cr0.96O4 was investigated, with focus on the influence of UV light and initial pH, degradation pathways and effect of Cr substation. The catalysts were prepared by a precipitation-oxidation method and characterized by chemical analysis, XRD, XAFS, TG-DSC, BET surface area and magnetometer. At pH 6.7 and under UV irradiation, almost complete degradation of TBBPA by Fe2.04Cr0.96O4 was accomplished within 240 min, and the leaching Fe ions were negligible. The substitution of chromium greatly increased the BET specific surface area and surface hydroxyl amount, which improved the heterogeneous UV/Fenton catalytic activity of magnetite. Moreover, Cr3+ on the octahedral sites enhanced the electron transfer process in the magnetite structure to accelerate the •OH generation. The produced •OH radicals preferentially attacked the C—Br bonds of TBBPA and then β-cleavaged the C—C bonds between benzene rings and isopropyl groups. The above results are of great significance for well understanding the effect of transition metal substitution on the UV/Fenton catalytic activity of magnetite and prospecting the application of magnetite minerals in environmental purification.

  研究了纳米晶 Fe3O4 和 Fe2.04Cr0.96O4 催化四溴双酚 A（TBBPA）的紫外/芬顿异相降解，重点考察了紫外光和初始 pH 值的影响、降解途径以及铬的亚基效应。催化剂采用沉淀氧化法制备，并通过化学分析、XRD、XAFS、TG-DSC、BET 表面积和磁力计进行表征。在 pH 值为 6.7 和紫外线照射条件下，Fe2.04Cr0.96O4 在 240 分钟内几乎完全降解了 TBBPA，且浸出的铁离子可以忽略不计。铬的取代大大增加了磁铁矿的 BET 比表面积和表面羟基量，提高了磁铁矿的异相紫外/芬顿催化活性。此外，八面体位点上的 Cr3+ 增强了磁铁矿结构中的电子传递过程，加速了 -OH 的生成。生成的 -OH 自由基优先攻击 TBBPA 的 C-Br 键，然后β-裂解苯环和异丙基之间的 C-C 键。上述结果对于深入理解过渡金属取代对磁铁矿紫外/芬顿催化活性的影响，以及探索磁铁矿在环境净化中的应用具有重要意义。
• Wood preservative compositions
  申请人：——

  公开号：US20040266885A1

  公开（公告）日：2004-12-30

  An insecticidal and termiticidal wood preservative composition contains as an active ingredient a compound of the formula: (I) wherein Y is a moiety selected from halogen, substituted aromatic ring and/or aliphatic residue, and n=1 to 4.

  一种杀虫和杀白蚁的木材防腐剂组合物含有一种式化合物作为活性成分：(I) 其中 Y 是选自卤素、取代芳环和/或脂肪族残基的分子，n 等于 1 至 4。
• Photochemical transformations of tetrabromobisphenol A and related phenols in water
  作者：Johan Eriksson、Sara Rahm、Nicholas Green、Åke Bergman、Eva Jakobsson

  DOI：10.1016/s0045-6535(03)00704-5

  日期：2004.1

  A method was developed for studies of the phototransformation at UV irradiation of aqueous solutions of tetrabromobisphenol A (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenol at various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbance spectra of the compounds and the emission spectra of the light-source were determined and used to calculate disappearance quantum yields of the photochemical reactions that were taking place. No major differences between the disappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yield of TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8 than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC-MS analysis and by comparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via different mechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenol and 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while the major degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane. (C) 2003 Elsevier Ltd. All rights reserved.
• MITCHELL, OLAN W.;MCKINNIE, BONNIE G.
  作者：MITCHELL, OLAN W.、MCKINNIE, BONNIE G.

  DOI：——

  日期：——
• WOOD PRESERVATIVE COMPOSITIONS
  申请人：Bromine Compounds Ltd.

  公开号：EP1409212A1

  公开（公告）日：2004-04-21