1,2,3,4,6-五氯萘 | 67922-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,2,3,4,6-五氯萘
• 英文名称: 1,2,3,4,6-Pentachloronaphthalene
• 英文别名: PCN-50；1,2,3,4,6-pentachloro-naphthalene；1,2,3,4,6-Pentachlor-naphthalin
• CAS: 67922-26-3
• 化学式: C₁₀H₃Cl₅
• 分子量: 300.399
• InChiKey: BAOLNVSMVTYGDA-UHFFFAOYSA-N

物化性质

• 沸点：
  373.7±37.0 °C(Predicted)
• 密度：
  1.638±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、乙酸乙酯（少量）、DCM
• 蒸汽压力：
  1.10e-06 mmHg
• 保留指数：
  2184.2

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• 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

反应信息

• 作为产物：
  描述：

  苯并[ghi]苝 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 1,2,3,4,6-五氯萘
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k

文献信息

• �ber die Sulfurierung der 1-Naphtol-3,6-disulfos�ure. (Eine weitere Ausnahme der Regel vonArmstrong &Wynne)
  作者：L. Blangey、H. E. Fierz-David、J. C. Ulrich、H. Bretscher

  DOI：10.1002/hlca.19510340215

  日期：——

  Durch energische Sulfurierung der 1-Naphtol-3,6-disulfosäure wurde die bisher unbekannte 1-Naphtol-2,3,4,6-tetra-sulfosäure hergestellt, und es wurde ihr Verhalten gegen Säuren, Alkalien und Ammoniak untersucht.

  1-萘酚-3,6-二磺酸的剧烈硫化制得了以前未知的1-萘-2,3,4,6-四磺酸，并研究了其对酸，碱和氨的行为。
• Degradation of one-side fully-chlorinated 1,2,3,4-tetrachloronaphthalene over Fe–Al composite oxides and its hypothesized reaction mechanism
  作者：Yalu Liu、Huijie Lu、Wenxiao Pan、Qianqian Li、Guijin Su、Minghui Zheng、Lirong Gao、Guorui Liu、Wenbin Liu

  DOI：10.1039/c7ra01775h

  日期：——

  aromatic ring, was evaluated over three of the prepared rod-like Fe–Al composite oxides (FeAl-1, FeAl-5 and FeAl-10). The results showed that their reactive activities were in the order of FeAl-5 ≈ FeAl-10 ≫ FeAl-1, which could be attributed to their different pore structural properties and reactive sites caused by the different phase interaction between iron species and the γ-Al2O3. The generation of

  在制备的三种棒状Fe-Al复合氧化物（FeAl-1，FeAl- 5和FeAl-10）。结果表明，它们的反应活性约为FeAl-5≈FeAl-10≫ FeAl-1，这可能归因于它们的孔结构性质和反应位点不同，这是由于铁物种与γ-之间的不同相间相互作用引起的。 Al 2 O 3。三氯萘（1,2,3-TrCN和1,2,4-TrCN，即CN-13和CN-14），二氯萘（1,2-DiCN，1,3-DiCN，1,4-DiCN）的生成和2,3-DiCN，即CN-3，CN-4，CN-5和CN-10）和一氯萘（1-MoCN和2-MoCN，即CN-1和CN-2）提示发生了连续的加氢脱氯反应。在三个不同的系统中，CN-14的含量从CN-13的71.5％增至77.7％，这表明在β位置发生了第一个加氢脱氯步骤是优选的。这与八氯萘（CN-75）脱氯过程中在微/纳米Fe 3 O 4上观察到的在α-位置的偏好不同。。一侧和
• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• Mil'tsov; Karavan; Nikiforov, Russian Journal of Organic Chemistry, 1999, vol. 35, # 5, p. 698 - 702
  作者：Mil'tsov、Karavan、Nikiforov、Tribulovich、Varentsov

  DOI：——

  日期：——
• De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes
  作者：F. Iino、T. Imagawa、M. Takeuchi、M. Sadakata

  DOI：10.1021/es980857k

  日期：1999.4.1

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.