1,2,3,4,5,6,7-heptachloronaphthalene | 32241-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4,5,6,7-heptachloronaphthalene
• 英文别名: 1H-heptachloronaphthalene
• CAS: 32241-08-0
• 化学式: C₁₀HCl₇
• 分子量: 369.289
• InChiKey: NDZIBNJHNBUHKW-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C
• 蒸汽压力：
  8.50e-08 mmHg
• 保留指数：
  2668.6

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  17
• 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

• 作为反应物：
  描述：

  1,2,3,4,5,6,7-heptachloronaphthalene 在 nitronium tetrafluoborate 、 sodium methylate 作用下， 以 环丁砜 、 乙腈 为溶剂， 反应 9.0h， 生成 heptachloro-8-methoxynaphthalene
  参考文献：
  名称：

  Brady, John H.; Tahir, Nazir; Wakefield, Basil J., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2425 - 2428

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基萘 在 二氯化二硫 、 三氯化铝 、 磺酰氯 、 硫酸 、 溴 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 四氯化碳 、 苯甲腈 为溶剂， 反应 145.25h， 生成 1,2,3,4,5,6,7-heptachloronaphthalene
  参考文献：
  名称：

  Extensive chlorination of methylnaphthalenes, Friedel-Crafts alkylation of pentachlorobenzene by heptachloro(chloromethyl)naphthalenes, and related results

  摘要：

  The chlorination of 2-methylnaphthalene (1) and 1-methylnaphthalene (12) by means of Silberrad's reagent (initial components: SO2Cl2, S2Cl2, and AlCl3) has been performed. From 1 or 12, the following compounds have been synthesized for first time: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene (3), nonachloro-7-(chloromethyl)-1,4-dihydronaphthalene (4), perchloro-3-vinylindene (2), perchloro-1-vinylindan, nonachloro-4-(chloromethyl)-1,4-dihydronaphthalene (11), heptachloro-7-(chloromethyl)naphthalene (6), heptachloro-8-(chloromethyl)naphthalene (10), heptachloro-7-methylnaphthalene, heptachloro-8-methylnaphthalene, 2-(bromochloromethyl)heptachloronaphthalene, 1-(bromochloromethyl)heptachloronaphthalene, heptachloro-7-formylnaphthalene (24), heptachloro-8-formylnaphthalene (26), (2-heptachloronaphthyl) (pentachlorophenyl)methane (17), and (1-heptachloronaphthyl) (pentachlorophenyl)methane (20). Silberrad's reagent interconverts dihydronaphthalenes 3 and 4. The AlCl3-promoted Friedel-Crafts alkylation of pentachlorobenzene (16) by naphthalenes 6 and 10, giving diarylmethanes 17 and 20, respectively, takes place in mild conditions (refluxing CS2) although the substrate and the alkylating agents are highly crowded polychloro compounds. By heating (100-degrees-C) a mixture of 17, 16, and AlCl3, 1H-heptachloronaphthalene (18) and bis(pentachlorophenyl)methane were obtained. Aldehyde 24, treated with Rh(PPh3)3Cl, gave 2H-heptachloronaphthalene, which was prepared in pure form for the first time. Under similar treatment, aldehyde 26 gave 18. The X-ray structures of indene 2 and dihydronaphthalene 11 are reported and discussed. Some probable mechanisms, as ell as IR, UV, and H-1 NMR spectra data of the compounds synthesized, are presented.

  DOI：

  10.1021/jo00047a026

文献信息

• 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
• Octachloroazulene
  作者：Yan Lou、Joanne Chang、Jeffrey Jorgensen、David M. Lemal

  DOI：10.1021/ja012051h

  日期：2002.12.1

  The title compound, the first perhaloazulene, has been synthesized from hexachlorobutadiene and cyclopentadiene. Further chlorination of 1,3,4,5,6,7-hexachloroazulene results in addition, not substitution, under electrophilic as well as free radical conditions. Radical chlorination of the hexachloroazulene affords in good yield a single decachlorotetrahydroazulene. Treatment of this Cl(10) compound

  由六氯丁二烯和环戊二烯合成了标题化合物，第一个全卤唑。1,3,4,5,6,7-六氯az唑在亲电子和自由基条件下进一步氯化而不是取代。六氯氮杂的自由基氯化提供了高产率的单一十氯四氢氮杂ene。用一当量的磷腈碱处理此Cl（10）化合物可得到九氯二氢杂氮烯，但第二等价物的加入会导致脱氯成1,2,3,4,5,6,7-庚七氯并脱氢成氯代。八氯氮杂烯。前三氮烯是通过酸催化或通过汞还原从Cl（9）化合物中干净地获得的。但是，在碳酸钙的存在下，Cl（9）中间体会产生深绿色的八氯氮杂烯。
• BRADY, J. H.;TAHIR, NAZIR;WAKEFIELD, B. J., J. CHEM. SOC. PERKIN TRANS., PT 1, 1984, N 10, 2425-2427
  作者：BRADY, J. H.、TAHIR, NAZIR、WAKEFIELD, B. J.

  DOI：——

  日期：——
• Extensive chlorination of methylnaphthalenes, Friedel-Crafts alkylation of pentachlorobenzene by heptachloro(chloromethyl)naphthalenes, and related results
  作者：R. Garcia、J. Riera、J. Carilla、L. Julia、E. Molins、C. Miravitlles

  DOI：10.1021/jo00047a026

  日期：1992.10

  The chlorination of 2-methylnaphthalene (1) and 1-methylnaphthalene (12) by means of Silberrad's reagent (initial components: SO2Cl2, S2Cl2, and AlCl3) has been performed. From 1 or 12, the following compounds have been synthesized for first time: nonachloro-3-(chloromethyl)-1,4-dihydronaphthalene (3), nonachloro-7-(chloromethyl)-1,4-dihydronaphthalene (4), perchloro-3-vinylindene (2), perchloro-1-vinylindan, nonachloro-4-(chloromethyl)-1,4-dihydronaphthalene (11), heptachloro-7-(chloromethyl)naphthalene (6), heptachloro-8-(chloromethyl)naphthalene (10), heptachloro-7-methylnaphthalene, heptachloro-8-methylnaphthalene, 2-(bromochloromethyl)heptachloronaphthalene, 1-(bromochloromethyl)heptachloronaphthalene, heptachloro-7-formylnaphthalene (24), heptachloro-8-formylnaphthalene (26), (2-heptachloronaphthyl) (pentachlorophenyl)methane (17), and (1-heptachloronaphthyl) (pentachlorophenyl)methane (20). Silberrad's reagent interconverts dihydronaphthalenes 3 and 4. The AlCl3-promoted Friedel-Crafts alkylation of pentachlorobenzene (16) by naphthalenes 6 and 10, giving diarylmethanes 17 and 20, respectively, takes place in mild conditions (refluxing CS2) although the substrate and the alkylating agents are highly crowded polychloro compounds. By heating (100-degrees-C) a mixture of 17, 16, and AlCl3, 1H-heptachloronaphthalene (18) and bis(pentachlorophenyl)methane were obtained. Aldehyde 24, treated with Rh(PPh3)3Cl, gave 2H-heptachloronaphthalene, which was prepared in pure form for the first time. Under similar treatment, aldehyde 26 gave 18. The X-ray structures of indene 2 and dihydronaphthalene 11 are reported and discussed. Some probable mechanisms, as ell as IR, UV, and H-1 NMR spectra data of the compounds synthesized, are presented.
• Brady, John H.; Tahir, Nazir; Wakefield, Basil J., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2425 - 2428
  作者：Brady, John H.、Tahir, Nazir、Wakefield, Basil J.

  DOI：——

  日期：——