6-溴苯并(a)芘 | 21248-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 6-溴苯并(a)芘
• 英文名称: 6-Bromobenzo[a]pyrene
• 英文别名: 6-bromobenzopyrene；6-Bromobenzo(A)pyrene
• CAS: 21248-00-0
• 化学式: C₂₀H₁₁Br
• 分子量: 331.211
• InChiKey: MJSYSGSEEADMTK-UHFFFAOYSA-N

物化性质

• 熔点：
  223.5°C
• 沸点：
  387.26°C (rough estimate)
• 密度：
  1.3975 (rough estimate)
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）
• 分解：
  When heated to decomposition it emits toxic fumes of ... /hydrogen bromide/.

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

多环芳烃的羟基化...以产生酚和二氢二醇是由微粒体酶催化的，并且可能涉及环氧的形成。预伯醇酸和相应的谷胱甘肽、半胱氨酰甘氨酸和半胱氨酸结合物...是...多环芳烃的主要代谢物...

HYDROXYLATION OF ... /POLYCYCLIC HYDROCARBONS/ TO GIVE PHENOLS & DIHYDRODIOLS IS CATALYZED BY MICROSOMAL ENZYMES & PROBABLY INVOLVES EPOXIDE FORMATION. PREMERCAPTURIC ACIDS & CORRESPONDING GLUTATHIONE, CYSTEINYLGLYCINE & CYSTEINE CONJUGATES ... ARE ... MAJOR METABOLITES OF ... /POLYCYCLIC HYDROCARBONS/

来源:Hazardous Substances Data Bank (HSDB)

代谢

多环芳烃苯并(a)芘(BaP)通过细胞色素P450的代谢形成苯并(a)芘醌类化合物的机制已经阐明。从未经诱导和经3-甲基胆蒽诱导的大鼠中制备Wistar大鼠肝微粒体，并将其与苯并(a)芘、6-氟苯并(a)芘(6FBP)、6-氯苯并(a)芘(6ClBP)或6-溴苯并(a)芘(6BrBP)一起孵育。代谢物通过高效液相色谱进行分析。NADPH和异丙基过氧化氢(CHP)被用作辅因子。在诱导的微粒体中，苯并(a)芘和6-氟苯并(a)芘在NADPH或异丙基过氧化氢的存在下显示出相似的代谢谱；两种化合物都能产生二氢二醇、酚和醌类化合物，而仅在使用异丙基过氧化氢时产生醌类化合物。在未诱导的微粒体和异丙基过氧化氢的存在下，苯并(a)芘和6-氟苯并(a)芘的代谢产生了相同的苯并(a)芘醌类化合物。未诱导的微粒体在NADPH的存在下能从苯并(a)芘中产生二氢二醇、酚和醌类化合物，而从6-氟苯并(a)芘中仅产生醌类化合物。6-氯苯并(a)芘和6-溴苯并(a)芘仅在诱导的微粒体和NADPH的存在下产生代谢物。研究了苯并(a)芘和6-氟苯并(a)芘的锰氧化以及苯并(a)芘和6-氟苯并(a)芘自由基阳离子高氯酸盐与水的反应。结果表明，苯并(a)芘和6-氟苯并(a)芘通过代谢形成苯并(a)芘醌类化合物只能来自它们的中间自由基阳离子。因此得出结论，苯并(a)芘和6-氟苯并(a)芘醌类化合物源于苯并(a)芘的初始单电子氧化形成其自由基阳离子。

The mechanism of formation of the benzo(alpyrene (BP) quinones from the metabolism of benzo(a)pyrene by cytochrome-p450 was delineated. Wistar-rat liver microsomes were prepared from uninduced and 3-methylcholanthrene induced rats and incubated with benzo(a)pyrene, 6-fluorobenzo(a)pyrene (6FBP), 6-chlorobenzo(a)pyrene (6ClBP), or 6-bromobenzo(a)pyrene (6BrBP). The metabolites were analyzed by high performance liquid chromatography. NADPH and cumene-hydroperoxide (CHP) were used as cofactors. Similar metabolic profiles were seen in the presence of NADPH or cumene-hydroperoxide with induced microsomes for benzo(a)pyrene and 6-fluorobenzo(a)pyrene; dihydrodiols, phenols and quinones were produced by both compounds with NADPH, while only quinones were produced with cumene-hydroperoxide. With uninduced microsomes and cumene-hydroperoxide, metabolism of benzo(a)pyrene and 6-fluorobenzo(a)pyrene produced the same benzo(a)pyrene quinones. Uninduced microsomes in the presence of NADPH produced dihydrodiols, phenols and quinones from benzo(a)pyrene, while only quinones were produced from 6-fluorobenzo(a)pyrene. 6-chlorobenzo(a)pyrene and 6-bromobenzo(a)pyrene produced metabolites only with induced nicrosomes and NADPH. The manganic oxidation of benzo(a)pyrene and 6-fluorobenzo(a)pyrene, and the reaction of benzo(a)pyrene and 6-fluorobenzo(a)pyrene radical cation perchlorates with water were investigated. Results indicated that metabolic formation of benzo(a)pyrene quinones from benzo(a)pyrene and 6-fluorobenzo(a)pyrene can only derive from their intermediate radical cation. /It was/ concluded that the benzo(a)pyrene and 6-fluorobenzo(a)pyrene quinones arise from an initial one electron oxidation of benzo(a)pyrene to its radical cation.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即进行急救：确保已经进行了充分的中毒物清洗。如果受害者停止呼吸，开始进行人工呼吸，最好使用训练过的需求阀复苏器、袋阀面罩装置或口袋面罩。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，防止窒息。保持受害者安静，维持正常体温。寻求医疗帮助。/芳香烃及其相关化合物/

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim 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 left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。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……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的咳嗽反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。/芳香烃及其相关化合物/

For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

许多具有亲电反应物类型的致癌物...会与DNA结合。...与...苯并(a)芘，通过其激活形式，7,8-二氢二醇-9,10-环氧物，发生/烷基化/反应是通过10号碳...到鸟嘌呤酸的2-氨基位置。此外，还存在与其他嘌呤和嘧啶的次要相互作用... /苯并(a)芘/

...NUMEROUS CARCINOGENS OF ELECTROPHILIC REACTANT TYPE...BIND TO DNA. ... WITH...B(A)P, THROUGH ITS ACTIVATED FORM, 7,8-DIHYDRODIOL-9,10-EPOXIDE, /ALKYLATION/ REACTION IS THRU 10 CARBON...TO THE 2-AMINO POSITION IN GUANYLIC ACID. IN ADDN, THERE ARE MINOR INTERACTIONS WITH OTHER PURINES & PYRIMIDINES... /BENZO(A)PYRENE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

... 研究已经证明，接触含有多种多环芳烃的焦炉排放物，导致了焦炉工人肺癌和泌尿生殖系统癌症死亡率的增加。/多环芳烃/

Mortality studies have demonstrated that exposure to coke oven emissions, which contain a variety of PAHs, caused increased incidences of lung and genitourinary cancer mortality in coke oven workers ... . /Polycyclic aromatic hydrocarbons/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

接触含有大量多环芳烃的杂酚油的工作人员患上了皮肤肿瘤... /多环芳烃/

Workers exposed to creosote containing numerous PAHs developed skin tumors ... . /Polycyclic aromatic hydrocarbons/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2903999090
• 储存条件：
  库房应保持干燥、低温和良好通风。

制备方法与用途

类别：有毒物质

可燃性危险特性：

• 热分解时会排出有毒的溴化氢烟雾。

储运特性：

• 应存放在干燥、低温且通风良好的库房中。

灭火剂：

• 可使用水、二氧化碳、沙土、泡沫或干粉进行扑灭。

反应信息

• 作为反应物：
  描述：

  6-溴苯并(a)芘 在 正丁基锂 、 过氯酰氟 作用下， 生成 6-氟苯并(a)芘
  参考文献：
  名称：

  One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation

  摘要：

  DOI：

  10.1021/jo00276a013
• 作为产物：
  描述：

  苯并[a]芘 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以86%的产率得到6-溴苯并(a)芘
  参考文献：
  名称：

  苯并[a]芘与脱氧鸟苷的C-8加合物的合成及光学性质

  摘要：

  8-(Benzo[a]pyren-6-yl)-2'-deoxyguanosine (Bp-dG) 是通过钯催化的 Suzuki-Miyaura 型交叉偶联反应从 6-苯并[a] 频哪醇酯制备的芘基硼酸和相应的溴化脱氧鸟苷前体。表征了 Bp-dG 的吸收和稳态荧光特性，并与 6-苯并‖a]芘的吸收和稳态荧光特性进行了比较。即使在紫外线照射下，修饰的核苷 Bp-dG 也对核苷水解表现出出乎意料的高稳定性。

  DOI：

  10.1055/s-2005-872262

文献信息

• POLYCYCLIC AROMATIC HYDROCARBON-BASED COMPOUNDS FOR MOLECULAR ELECTRONIC DEVICE AND MOLECULAR ELECTRONIC DEVICES COMPRISING SAME
  申请人：Korea University Research and Business Foundation

  公开号：US20210367154A1

  公开（公告）日：2021-11-25

  The present invention relates to polycyclic aromatic hydrocarbon-based compounds, for a molecular electronic device, enabling molecular rectification, and molecular electronic devices comprising a molecular layer formed by means of the compounds self-assembled on an electrode. The compounds according to the present invention can realize rectifying properties by being introduced between electrodes and thus enable a high rectification ratio by means of low voltage driving, and thus can be substituted for a silicon-based diode device and, more particularly, can be utilized for a wearable device, Bluetooth, an IoT enabling device and the like which require low voltage driving.

  本发明涉及基于多环芳烃的化合物，用于分子电子器件，实现分子整流，并且包括由这些化合物自组装在电极上形成的分子层的分子电子器件。根据本发明的化合物可以通过介入电极之间实现整流特性，从而通过低电压驱动实现高整流比，因此可以替代基于硅的二极管器件，更具体地，可以用于低电压驱动的可穿戴设备、蓝牙、物联网设备等需要低电压驱动的设备。
• Radical cations of benzo[α]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA
  作者：D. E. Stack、P. Cremonesi、A. Hanson、E. G. Rogan、E. L. Cavalieri

  DOI：10.3109/00498259509061890

  日期：1995.1

  1. Oxidation of benzo[a]pyrene (BP) by I2 in the presence of AgClO4 in benzene generates the BP.+ClO4-.AgI complex. This same method was used to produce radical cations from 6-FBP, 6-ClBP, 6-BrBP and 6-CH3BP. 2. Reaction of the BP, 6-FBP, 6-ClBP and 6-BrBP radical cation perchlorates with H2O produced BP 1,6-, 3,6- and 6,12- dione, whereas 6-CH3BP.+ClO4-.AgI yielded 6-CH2OHBP. 3. When BP.+ClO4-.AgI

  1.在Ag 在苯中的存在下，I2氧化苯并[a] py（BP），生成BP。+ ClO4-.AgI复合物。使用相同的方法由6-FBP，6-ClBP，6-BrBP和6-CH3BP产生自由基阳离子。2.BP，6-FBP，6-ClBP和6-BrBP自由基阳离子高氯酸盐与H 2 O反应生成BP 1,6-，3,6-和6,12-二酮，而6-CH3BP。+ -。 AgI产生6-CH 2 OHBP。3.当BP。+ -.AgI和6-FBP。+ -.AgI与NaOAc在H2O / CH3CN（9：1）中反应时，除醌外，还形成了6-OAcBP。在6-ClBP。+ -.AgI的情况下，除了二酮以外，还形成少量的1-OAc-6-ClBP和3-OAc-6-ClBP，而对于6-BrBP和6-CH3BP反应产物分别为BP二酮和6-CH 2 OHBP。4.这些结果证实了电荷在BP。+中位于
• Efficient Syntheses of <i>C</i>⁸-Aryl Adducts of Adenine and Guanine Formed by Reaction of Radical Cation Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons with DNA
  作者：Qing Dai、Daiwang Xu、Keunpoong Lim、Ronald G. Harvey

  DOI：10.1021/jo070518m

  日期：2007.6.1

  The synthesis of the C8-aryl adducts of adenine and guanine formed by reaction of the radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BP) and dibenzo[def,p]chrysene (DBC), with DNA is reported. The synthetic approach involves in the key step direct reaction of a PAH aldehyde with a di- or triamine precursor of a purine. The method is operationally

  所述的合成Ç 8腺嘌呤和鸟嘌呤的芳基的加合物通过致癌的多环芳香烃（PAHs），如苯并[的自由基阳离子的代谢物的反应而形成一个]芘（BP）和二苯并[ DEF，p ]屈（chrysene）（DBC ），带有DNA的报道。合成方法的关键步骤是将PAH醛与嘌呤的二胺或三胺前体直接反应。该方法操作简单，提供良好的加合物收率，并且范围广泛。衍生自BP（6-BP-8-Ade和6-BP-8-Gua）和DBC（10-DBC-8-Ade和10-DBC-8-Gua）的腺嘌呤和鸟嘌呤的C 8芳基加合物为通过这种方法以高收率合成。类似的C 8其他多环芳烃（蒽，苯并[ a ]蒽和）的芳基腺嘌呤和鸟嘌呤衍生物也很容易通过这种方法制备。这种合成方法优于目前可用的唯一方法。它需要短寿命的PAH自由基阳离子（通过电化学或化学方法生成）与2'-脱氧核糖核苷或相应的嘌呤碱基直接反应。它以低收率提供加合物，并伴随有复杂的副产物混合
• Synthesis of Pyrene and Benzo[<i>a</i>]pyrene Adducts at the Exocyclic Amino Groups of 2‘-Deoxyadenosine and 2‘-Deoxyguanosine by a Palladium-Mediated C−N Bond-Formation Strategy
  作者：Mahesh K. Lakshman、Felix N. Ngassa、Suyeal Bae、Dennis G. Buchanan、Hoh-Gyu Hahn、Heduck Mah

  DOI：10.1021/jo030113b

  日期：2003.7.1

  with the purine 2'-deoxynucleosides to date. In this paper we disclose the synthesis of the model adducts N(6)-(1-pyrenyl)-2'-deoxyadenosine and N(2)-(1-pyrenyl)-2'-deoxyguanosine as well as the first synthesis of the carcinogen-linked nucleoside derivatives N(6)-(6-benzo[a]pyrenyl)-2'-deoxyadenosine and N(2)-(6-benzo[a]pyrenyl)-2'-deoxyguanosine via a palladium-mediated C-N bond formation. Two different

  致癌的烃类苯并[a] py（BaP）的单电子氧化被认为会产生自由基阳离子中间体，并且已经提出该物种会在嘌呤核碱基的氮原子上引起烷基化。尽管已经分离出了几种不同的核苷加合物，它们是由这种代谢活化模式引起的，但是迄今为止，还没有选择性，全合成的任何烃与嘌呤2'-脱氧核苷的单电子氧化形成的稳定的环外氨基加合物。 。在本文中，我们公开了模型加合物N（6）-（1-pyrenyl）-2'-脱氧腺苷和N（2）-（1-pyrenyl）-2'-脱氧鸟苷的合成以及该化合物的第一个合成。致癌物连接的核苷衍生物N（6）-（6-苯并[a]苯甲酰基）-2'-脱氧腺苷和N（2）-（6-苯并[a]苯甲酰基）-2' -脱氧鸟苷通过钯介导的CN键形成。尝试了两种不同的偶联策略：将芳基溴化物与适当保护的核苷偶联以及将芳基胺与适当的卤核苷偶联。前者的适用性有限，因为通过这种方法仅制备了N（6）-（1-吡啶基）-2'-脱氧腺苷。另
• Specifically tritiated arene oxides
  作者：Haruhiko Yagi、Patrick Dansette、Donald M. Jerina

  DOI：10.1002/jlcr.2580120115

  日期：1976.1

  Convenient methods have been developed for the preparation of specifically tritiated arene oxides. K-Region arene oxides of phenanthene, benzo[a]anthracene and benzo[a]pyrene were prepared from triatiated cis dihydrodiols via the methoxydioxolane route and the non-K-region arene oxides, benzo[a]pyrene 7,8- and 9,10-oxide, were prepared via triated halphydrin esters.

  已经开发了用于制备特定氚化芳烃氧化物的便利方法。菲、苯并[a]蒽和苯并[a]芘的K区芳烃氧化物通过甲氧基二氧戊环路线和非K区芳烃氧化物、苯并[a]芘7,8-和9由三化顺式二氢二醇制备,10-氧化物是通过三化卤代醇酯制备的。