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1,2-苯并芴 | 238-84-6

中文名称
1,2-苯并芴
中文别名
1,2-苯并茀;11H-苯并[a]芴;柯芴
英文名称
benzo[a]fluorene
英文别名
11H-benzo[a]fluorene;1,2-benzofluorene;benzofluorene;benz[a]fluorene
1,2-苯并芴化学式
CAS
238-84-6;30777-18-5
化学式
C17H12
mdl
MFCD00039578
分子量
216.282
InChiKey
HKMTVMBEALTRRR-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    185-190 °C
  • 沸点:
    407°C(lit.)
  • 密度:
    1.1020 (estimate)
  • 闪点:
    11 °C
  • 溶解度:
    在二恶烷中的溶解度为0.1g/10mL,透明,无色
  • 最大波长(λmax):
    433nm(THF)(lit.)
  • 物理描述:
    COLOURLESS PLATE-LIKE CRYSTALS.
  • 颜色/状态:
    White or off-white powder
  • 蒸汽压力:
    2.43X10-7 mm Hg at 25 °C
  • 亨利常数:
    2.66e-05 atm-m3/mole
  • 稳定性/保质期:

    Stable under recommended storage conditions.[Sigma-Aldrich; Safety Data Sheet for 11H-Benzo

  • 分解:
    When heated to decomposition it emits acrid smoke and irritating vapors.
  • 汽化热:
    Enthalpy of vaporization: 83.7 kJ/mol at 398 K
  • 相对蒸发率:
    Evaporation at 20 °C is negligible
  • 保留指数:
    2167.6;2228.1;2178;2221;2221;2180;2221;2198.8;2226.8;366.5;366.7;367.5;364.44;364.45;364.86;365.4;364.9

计算性质

  • 辛醇/水分配系数(LogP):
    5.7
  • 重原子数:
    17
  • 可旋转键数:
    0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.058
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

毒理性
  • 毒性总结
鉴定和使用:苯并(a)是一种多环芳烃(PAH)。除了在PAH的生物化学研究中外,它没有商业用途。人体研究:苯并(a)作为环境中多核芳烃化合物总量中的少量成分存在。人类接触苯并(a)主要通过吸烟、吸入污染空气以及摄入含有燃烧产物的食物和。动物研究:在一项研究中,通过皮肤应用测试了苯并(a)对小鼠的致癌性,并在小鼠皮肤启动-促进试验中进行了测试。两项研究均得到了阴性结果。在涉及将苯并(a)皮下注射到小鼠的研究中,没有观察到注射部位的肿瘤。现有数据不足以评估苯并(a)对鼠伤寒沙门氏菌的致突变性。生态毒性研究:苯并(a)是一种已知的芳基烃受体(AhR)激动剂。
IDENTIFICATION AND USE: Benzo(a)fluorene is a polycyclic aromatic hydrocarbon (PAH). It does not have a commercial use, other than in biochemical research of PAH. HUMAN STUDIES: Benzo(a)fluorene is present as a minor component of the total content of polynuclear aromatic compounds in the environment. Human exposure to benzo(a)fluorene occurs primarily through the smoking of tobacco, inhalation of polluted air and by ingestion of food and water contaminated with combustion products. ANIMAL STUDIES: Benzo(a)fluorene was tested for carcinogenicity in mice in one study by skin application and in a mouse-skin initiation-promotion assay. Negative results were obtained in both studies. In a study involving subcutaneous administration of benzo(a)fluorene to mice, no injection-site tumor was observed. The available data were inadequate to evaluate the mutagenicity of benzo(a)fluorene to Salmonella typhimurium. ECOTOXICITY STUDIES: Benzo(a)fluorene is a known aryl hydrocarbon receptor (AhR) agonist.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
苯并[a]及其同类物对人类致癌性不可分类(第3组)。
benzo[a]fluorene /and analogs/ are not classifiable as to their carcinogenicity to humans (Group 3).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌物分类
国际癌症研究机构致癌物:苯并[a]
IARC Carcinogenic Agent:Benzo[a]fluorene
来源:International Agency for Research on Cancer (IARC)
毒理性
  • 致癌物分类
国际癌症研究机构(IARC)致癌物分类:第3组:无法归类其对人类致癌性
IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans
来源:International Agency for Research on Cancer (IARC)
毒理性
  • 致癌物分类
国际癌症研究机构专著:第92卷:(2010年)一些非杂环多环芳烃及其相关暴露
IARC Monographs:Volume 92: (2010) Some Non-heterocyclic Polycyclic Aromatic Hydrocarbons and Some Related Exposures
来源:International Agency for Research on Cancer (IARC)

安全信息

  • 危险等级:
    6.1(b)
  • 危险品标志:
    F,T
  • 危险类别码:
    R23/24/25,R39/23/24/25,R11
  • 海关编码:
    2902909090
  • 包装等级:
    III
  • 危险类别:
    6.1(b)
  • WGK Germany:
    3
  • 危险品运输编号:
    UN 2811

SDS

SDS:28bdb602bdbc696fe3b5d50d6f1a0bae
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

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文献信息

  • Au-Catalyzed Biaryl Coupling To Generate 5- to 9-Membered Rings: Turnover-Limiting Reductive Elimination versus π-Complexation
    作者:Tom J. A. Corrie、Liam T. Ball、Christopher A. Russell、Guy C. Lloyd-Jones
    DOI:10.1021/jacs.6b10018
    日期:2017.1.11
    The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates
    已经从机理和制备方面研究了分子内催化芳基三甲基硅烷芳烃的芳基化。该反应生成 5 至 9 元环,在研究的 44 个实例中,10 个包含杂原子 (N, O)。芳烃与芳基硅烷的束缚不仅提供了一种工具来探测 Ar-Au-Ar 中间体的构象灵活性的影响,通过芳基-芳基键的长度的系统调制,而且还提供了将中性和电子芳基化的能力在分子间过程中根本不发生反应的劣质芳烃底物。使分子内芳基化也导致了现象学上更简单的反应动力学,总体而言,这些特征促进了对线性自由能关系、动力学同位素效应、以及关于芳基电子需求和构象自由度对二芳基 (III) 物种还原消除速率影响的第一个定量实验数据。形成一系列生物的周转限制步骤对芳烃的反应性很敏感,并且对于带有强吸电子取代基的芳烃(σ > 0.43)从还原消除变为 π 络合。一个或两个环上的给电子取代基 (ρ = -2.0) 加速了还原消除,单个 σ 值本质上是可加的。两个芳环之间更长和更灵活的系链导致从
  • Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp<sup>2</sup>)–H Bond Functionalization
    作者:Shuai Xu、Ri Chen、Zihao Fu、Qi Zhou、Yan Zhang、Jianbo Wang
    DOI:10.1021/acscatal.6b03562
    日期:2017.3.3
    A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C–C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source
    已经开发出了一种高效且操作简单的催化的正[4 +1]环化反应。该反应的特征是在羧基中心上形成两个不同的C–C键。它代表了一种简便的方法,用于合成多种多环芳烃(PAH)和1 H-,并以易于获得的(三甲基甲硅烷基)重氮甲烷作为卡宾源。属卡宾迁移插入和C(sp 2)–H键活化被提议为该转变的关键步骤。该反应进一步证明了与各种过渡属催化的转化结合的基于卡宾的偶联的多功能性。
  • Palladium-Catalyzed Reaction of Haloarenes with Diarylethynes: Synthesis, Structural Analysis, and Properties of Methylene-Bridged Arenes
    作者:Che-Wei Lee、En-Chih Liu、Yao-Ting Wu
    DOI:10.1021/acs.joc.5b02111
    日期:2015.11.6
    Fluorenes and methylene-bridged polyarenes were easily and efficiently synthesized from haloarenes (or aryl triflates) and diarylethynes by a one-pot, two-step procedure. This protocol involves the palladium-catalyzed cycloisomerization and a subsequent base-mediated retro-aldol condensation. A major advantage is that the starting materials need not have ortho functional groups to complete the annulation
    和亚甲基桥接的聚芳烃可以通过一锅,两步程序从卤代芳烃(或芳基三氟甲磺酸酯)和二芳基乙炔轻松高效地合成。该方案涉及催化的环异构化和随后的碱介导的逆醛醇缩合。一个主要的优点是,起始材料不需要具有邻位官能团即可完成环化反应。使用二卤代芳烃,高度π-共轭卤代芳烃或二芳基炔烃扩大了设计产品的骨架。苯并[ a]的形成机理对]进行了研究。通过X射线晶体学证实了亚甲基桥联的环戊烯的碗状结构。研究了由此制备的产物的光物理和电化学性质。
  • East Timor and the new humanitarian interventionism
    作者:Nicholas J. Wheeler、Tim Dunne
    DOI:10.1111/1468-2346.00220
    日期:2001.10
    The fate of East Timor provides a barometer for how far the normative structure of international society has been transformed since the end of the Cold War. In 1975, the East Timorese were abandoned by a Western bloc that placed accommodating the Indonesian invasion of the island before the protection of human rights. Twenty-five years later, it was the protection of the civilian population on the island that loomed large in the calculations of these same states. Australia, which had sacrificed the rights of the people of East Timor on the altar of good relations with Indonesia, found itself leading an intervention force that challenged the old certainties of its ‘Jakarta first’ policy. The article charts the interplay of domestic and international factors that made this normative transformation possible. The authors examine the political and economic factors that led to the agreement in May 1999 between Portugal, Indonesia and the UN to hold a referendum on the future political status of East Timor. A key question is whether the international community should have done more to assure the security of the ballot process. The authors argue that while more could have been done by Australia, the United States and officials in the UN Secretariat to place this issue on the Security Council's agenda, it is highly unlikely that the international community would have proved capable of mobilizing the political will necessary to coerce Indonesia into accepting a peacekeeping force.The second part of the article looks at how the outbreak of the violence in early September 1999 fundamentally changed these political assumptions. The authors argue that it became politically possible to employ coercion against Indonesian sovereignty in a context in which the Habibie government was viewed as having failed to exercise sovereignty with responsibility. By focusing on the economic and military sanctions employed by Western states, the pressures exerted by the international financial institutions and the intense diplomatic activity at the UN and in Jakarta, the authors show how Indonesian political and military leaders were prevailed upon to accept an international force. At the same time, Australian reporting of the atrocities and how this prompted the Howard government to an intervention that challenged traditional conceptionsof Australia's vital interests, is considered. The conclusion reflects on how thiscase supports the claim that traditional notions of sovereignty are increasinglyconstrained by norms of humanitarian responsibility.
    东帝汶的命运为冷战刚刚结束以来国际社会的规范结构发生了多大的改变提供了晴雨表。1975年,东帝汶遭到了西方阵营的抛弃.该阵营把容忍印度尼西亚对东帝汶的入侵放在了保护人权之前。二十五年后,保护该岛平民成为这些国家最关心的事。曾经牺牲东帝汶人民权利并以此换取与印度尼西亚良好关系的澳大利亚发现自己正领导一支干预力量,对本国“雅加达优先”政策的老传统提出了挑战。本文着重描述了使得这一规范转变成为可能的国内外因素之间的相互作用。作者们探讨了导致1999年5月葡萄牙、印度尼西亚与联合国达成在东帝汶举行关于未来政治地位的全民公决协议的政治与经济因素。一个关键问题是,国际社会是否本应采取更多的行动来确保全民公决过程的安全。作者们认为,尽管澳大利亚、美国与联合国秘书处的官员们本可以采取更多的行动把这一问题放在联合国安理会的议程表上,但是国际社会已经不可能具有动员必要的政治意愿来迫使印度尼西亚接受一支维和部队的能力了。 本文的第二部分研究了1999年9月初爆发的暴力是怎样从根本改变了这些政治假定的。作者们认为,如果将哈比比政府视为一个没有负责任地使用主权的政府,那么在这样的情形下,对印度尼西的主权使用强制就是政治上可能的。作者们将重点放在为了迫使印度尼西亚接受一支国际部队,西方国家所实施的经济与军事制裁、国际融机构施加的压力,以及联合国和雅加达的紧张外交活动。同时,还考虑到澳大利亚有关暴行的报道是怎样促使霍华德发动了这场干预行动的,这场干预行动挑战了澳大利亚关键利益的旧有传统观念。结论部分就这一事例如何支持如下主张进行了思考:传统的主权观念由于人道主义责任的规范而日益受到制约。
  • Synthese und Polymerisationseigenschaften substituierter ansa-Bis(fluorenyliden)komplexe des Zirconiums
    作者:Peter Schertl、Helmut G. Alt
    DOI:10.1016/s0022-328x(99)00074-1
    日期:1999.6
    The steric and electronic influence of various substituents at different positions of the fluorenylidene fragment effects the catalytical properties of the MAO activated bis(fluorenylidene) complexes [C13H8−nRn(CH2)2C13H8−nRn]ZrCl2 (n=0–2; R=H, alkyl, aryl, (CH)4, OCH3). We report the synthesis and characterization of 27 new ansa bis(fluorenylidene) zirconium dichloride complexes and illustrate
    各种取代基中的的片段的效果的不同位置的空间和电子影响MAO的催化性质活化双(基)配合物[C 13 ħ 8- ñ - [R Ñ (CH 2)2 C 13 ħ 8- Ñ ř ñ ]的ZrCl 2(ñ = 0-2; R = H,烷基,芳基,(CH)4 ,OCH 3)。我们报告了27种新ansa的合成和表征双(基)二配合物,并说明了它们在乙烯的均相催化聚合中的应用。将获得的结果与已知的双(基)配合物进行比较。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
hnmr
mass
cnmr
ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(S)-2-N-Fmoc-氨基甲基吡咯烷盐酸盐 (2S,4S)-Fmoc-4-三氟甲基吡咯烷-2-羧酸 黎芦碱 鳥胺酸 魏因勒卜链接剂 雷迪帕韦二丙酮合物 雷迪帕韦中间体6 雷迪帕韦 雷迪帕维中间体 雷迪帕维中间体 雷尼托林 锰(2+)二{[乙酰基(9H-芴-2-基)氨基]氧烷负离子} 醋酸丁酸纤维素 达托霉素杂质 赖氨酸杂质4 试剂9,9-Dioctyl-9H-fluoren-2-amine 螺[环戊烷-1,9'-芴] 螺[环庚烷-1,9'-芴] 螺[环己烷-1,9'-芴] 螺[3.3]庚烷-2,6-二-(2',2'',7',7''-四碘螺芴) 螺-(金刚烷-2,9'-芴) 螺(环己烷-1,9'-芴)-3-酮 藜芦托素 荧蒽 反式-2,3-二氢二醇 草甘膦-FMOC 英地卡胺 苯芴醇杂质A 苯甲酸-(芴-9-基-苯基-甲基酯) 苯甲酸-(9-苯基-芴-9-基酯) 苯并[b]芴铯盐 苯并[a]芴酮 苯基芴胺 苯基(9-苯基-9-芴基)甲醇 苯(甲)醛,9H-芴-9-亚基腙 苯(甲)醛,4-羟基-3-甲氧基-,(3-甲基-9H-茚并[2,1-c]吡啶-9-亚基)腙 芴甲氧羰酰胺 芴甲氧羰酰基高苯丙氨酸 芴甲氧羰酰基肌氨酸 芴甲氧羰酰基环己基甘氨酸 芴甲氧羰酰基正亮氨酸 芴甲氧羰酰基D-环己基甘氨酸 芴甲氧羰酰基D-Β环己基丙氨酸 芴甲氧羰酰基-O-三苯甲基丝氨酸 芴甲氧羰酰基-D-正亮氨酸 芴甲氧羰酰基-6-氨基己酸 芴甲氧羰基-高丝氨酸内酯 芴甲氧羰基-缬氨酸-1-13C 芴甲氧羰基-叔丁基二甲基硅-D-丝氨酸 芴甲氧羰基-beta-赖氨酰酸(叔丁氧羰基) 芴甲氧羰基-S-叔丁基-L-半胱氨酸五氟苯基脂