2,3,4,5,6-五氯苯甲酸 | 1012-84-6

• 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: 2,3,4,5,6-五氯苯甲酸
• 英文名称: perchlorobenzoic acid
• 英文别名: Pentachlorbenzoesaeure；pentachlorobenzoic acid；2,3,4,5,6-pentachlorobenzoic acid
• CAS: 1012-84-6
• 化学式: C₇HCl₅O₂
• mdl: MFCD00092425
• 分子量: 294.349
• InChiKey: IONYGGJUUJFXJK-UHFFFAOYSA-N

物化性质

• 熔点：
  209.3°C
• 沸点：
  379.1±37.0 °C(Predicted)
• 密度：
  1.7324 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-五氯苯甲酸 在 氯化亚砜 作用下， 反应 48.0h， 以61%的产率得到五氯苯甲酰氯
  参考文献：
  名称：

  Photochemical behavior of stable free radicals: the photochemistry of perchlorodiphenylmethyl radical

  摘要：

  The excitation of perchlorodiphenylmethyl radical (PDM) at 530 nm leads to the lowest excited doublet, D1 (tau = 31 ns), from which emission is observed (PHI = 1 X 10(-3) +/- 0.0003). This state is quenched by electron donors and acceptors at a rate at or close to diffusion control and at much slower rates by oxygen and hydrogen atom donors. Fragmentation of PDM (PHI(d) = 0.06) occurs from a higher excited doublet (D(n), n greater-than-or-equal-to 2) producing intermediates that are trapped by O2, chlorine, or hydrogen donors, yielding products 1-6. Experimental evidence suggests a structure-photoreactivity correlation in the perchlorinated arylmethyl radicals in which the partitioning between photochemical cyclization or fragmentation depends on the twist angle between the appended phenyl rings.

  DOI：

  10.1021/j100103a025
• 作为产物：
  描述：

  3,4-二氯苯甲酸 在 盐酸 、 manganese(IV) oxide 作用下， 生成 2,3,4,5,6-五氯苯甲酸
  参考文献：
  名称：

  Claus; Buecher, Chemische Berichte, 1887, vol. 20, p. 1621

  摘要：

  DOI：
• 作为试剂：
  描述：

  9-十八烯 在 咪唑 、 2,3,4,5,6-五氯苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-phenyl-8-octadecenyl-10-urethane
  参考文献：
  名称：

  由9,10-环氧十八烷和苯基异氰酸酯形成恶唑烷酮的研究

  摘要：

  AbstractThe formation of oxazolidone from 9,10‐epoxyoctadecane and phenylisocyanate was studied. One branch of epoxidized vegetable oil with one epoxy group per chain corresponds to 9,10‐epoxyoctadecane. This model could explain the probability of oxazolidone formation from natural oil‐derived epoxides. Epoxidized natural oils are TG consisting of glycerin and three FA with or without one to three epoxy groups in the middle of the chain. To study oxazolidone formation from an internal epoxy group without possible interference from the side reactions on the ester group, 9,10‐epoxyoctadecane was selected as the most appropriate model compound. Epoxy groups in the middle of allong aliphatic chain are of low reactivity toward isocyanates, and preparation of oxazolidones requires fairly harsh conditions such as high temperatures and catalysts, which also promote side reactions. The dominant side reaction is rearrangement of the epoxy groups. We found that the direction and magnitude of the rearrangement and the yield of any particular product depended on the catalyst used. Lithium chloride, aluminum trichloride, and zinc iodide catalyzed oxazolidone formation, along with the catalysis of side reactions such as ketone and carbonate formation. Aluminum trichloride showed the highest conversion of 9,10‐epoxyoctadecane to oxazolidone. Aluminum triisopropoxide, triphenylantimony iodide, and imidazole did not catalyze the formation of oxazolidone. They were effective as catalysts of epoxy group rearrangement and promoted the formation of hydroxyl, ketone, and carbonate compounds. Hydroxyl groups reacted with isocyanate to produce urethane.

  DOI：

  10.1007/s11746-003-0744-7

文献信息

• [EN] LOW VISCOSITY IONIC LIQUIDS<br/>[FR] LIQUIDES IONIQUES DE FAIBLE VISCOSITÉ
  申请人：INVISTA TECH SARL

  公开号：WO2011100232A1

  公开（公告）日：2011-08-18

  Disclosed is an ionic liquid formula (I): wherein: n is 1 or 2; R1 is selected from H and (C1-C6)alkyl; R2 is selected from -(CH2)wO[(CH2)xO(CH2)y]m(CH2)zCH3 and wherein w is 1 to 6, x is 1 to 6, y is 0 to 6, z is 0 to 6, m is 0 to 3 and [w+m(x+y)+z] is less than or equal to 12; and R3 is selected from H and methyl, wherein if n is 1 then R3 is methyl, and if n is 2 then R3 is H. Also disclosed are electrochemical devices and devices employing such electrochemical devices as energy sources.

  揭示了一种离子液体配方（I）：其中：n为1或2；R1从H和（C1-C6）烷基中选择；R2从-(CH2)wO[(CH2)xO(CH2)y]m(CH2)zCH3中选择，其中w为1至6，x为1至6，y为0至6，z为0至6，m为0至3，[w+m(x+y)+z]小于或等于12；R3从H和甲基中选择，如果n为1，则R3为甲基，如果n为2，则R3为H。还公开了使用这种离子液体的电化学器件和使用这种电化学器件作为能源源的器件。
• LOW VISCOSITY IONIC LIQUIDS
  申请人：Seddon Kenneth Richard

  公开号：US20120050945A1

  公开（公告）日：2012-03-01

  Disclosed is an ionic liquid: wherein: n is 1 or 2; R 1 is selected from H and (C 1 -C 6 )alkyl; R 2 is selected from —(CH 2 ) w O[(CH 2 ) x O(CH 2 ) y ] m (CH 2 ) z CH 3 and wherein w is 1 to 6, x is 1 to 6, y is 0 to 6, z is 0 to 6, m is 0 to 3 and [w+m(x+y)+z] is less than or equal to 12; and R 3 is selected from H and methyl, wherein if n is 1 then R 3 is methyl, and if n is 2 then R 3 is H. Also disclosed are electrochemical devices and devices employing such electrochemical devices as energy sources.

  揭示了一种离子液体： 其中： n为1或2； R1从H和(C1-C6)烷基中选择； R2从—(CH2)wO[(CH2)xO(CH2)y]m(CH2)zCH3中选择， 其中w为1至6，x为1至6，y为0至6，z为0至6，m为0至3， [w+m(x+y)+z]小于或等于12；以及 R3从H和甲基中选择，其中 如果n为1，则R3为甲基， 如果n为2，则R3为H。 还公开了使用这种离子液体的电化学器件和使用这种电化学器件作为能源源的器件。
• Method for Estimating S_N1 Rate Constants: Solvolytic Reactivity of Benzoates
  作者：Mirela Matić、Bernard Denegri、Olga Kronja

  DOI：10.1021/jo3013308

  日期：2012.10.19

  pentafluorobenzoate (PFB) and 2,4,6-trifluorobenzoate (TFB) leaving groups have been derived from the solvolysis rate constants of X,Y-substituted benzhydryl PFBs and TFBs measured in a series of aqueous solvents, by applying the LFER equation: log k = sf(Ef + Nf). The heterolysis rate constants of dianisylmethyl PFB and TFB, and those determined for 10 more dianisylmethyl benzoates in aqueous ethanol,

  五氟苯甲酸酯（PFB）和2,4,6-三氟苯甲酸酯（TFB）离开基团的核官能度是通过应用LFER方程从在一系列水性溶剂中测量的X，Y取代的苯甲基PFB和TFB的溶剂分解速率常数得出的：log k = s f（E f + N f）。二苯胺基甲基PFB和TFB的杂解速率常数，以及在乙醇水溶液中另外10种苯甲酰甲基苯甲酸酯的杂化速率常数，构成了一组参考苯甲酸酯，其实验ΔG with与ΔH correlat相关。（通过PCM量子化学方法计算）模型环氧环的形成。由于具有极好的相关性（r = 0.997），因此已经建立了计算取代苯甲酸酯LG的核官能度的方法，最终提供了一种测定给定溶剂中任何苯甲酸酯的S N 1反应性的方法。使用Δ ģ ⧧ VSΔ ħ ⧧的相关性，并考虑小号˚F基于相似性，已在90％，80％和70％的乙醇水溶液中确定了约70种苯甲酸酯的核官能度参数。计算得出的取代苯甲酸酯离去基团的固有壁垒
• NOVEL PHENOL DERIVATIVE
  申请人：Kobashi Seiichi

  公开号：US20120184587A1

  公开（公告）日：2012-07-19

  Disclosed are a novel compound and a pharmaceutical product, each having a remarkable uricosuric effect. Specifically disclosed are: a novel phenol derivative represented by general formula (1) that is shown in FIG. 1 ; a pharmaceutically acceptable salt thereof; a hydrate of the derivative or the salt; and a solvate of the derivative or the salt. (In the formula, R 1 and R 2 may be the same or different and each represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylsulfanyl group, an alkylsulfinyl group, an alkylsulfonyl group, a lower alkyl-substituted carbamoyl group, a saturated nitrogen-containing heterocyclic N-carbonyl group, a halogen atom, a cyano group or a hydrogen atom; R 3 represents a lower alkyl group, a haloalkyl group, a halogen atom, a hydroxy group or a hydrogen atom; and X represents a sulfur atom, an —S(═O)— group or an —S(═O) 2 — group.)

  揭示了一种新型化合物和一种药物产品，每种都具有显著的利尿酸效果。具体揭示了：一种新型酚衍生物，其通式（1）如图1所示；其药学上可接受的盐；该衍生物或盐的水合物；以及该衍生物或盐的溶剂化合物。（在该式中，R1和R2可以相同也可以不同，每个代表较低的烷基基团、较低的烯基基团、较低的炔基基团、较低的烷氧基团、卤代烷基基团、卤代烷氧基团、烷基硫基团、烷基亚硫基团、烷基磺基团、较低烷基取代的氨基甲酰基团、饱和的含氮杂环N-羰基团、卤素原子、氰基或氢原子；R3代表较低的烷基基团、卤代烷基基团、卤素原子、羟基或氢原子；X代表硫原子、—S(═O)—基团或—S(═O)2—基团。）
• Electrocarboxylation of Chlorinated Aromatic Compounds
  作者：Dirk Golinske、Jürgen Voss、Gunadi Adiwidjaja

  DOI：10.1135/cccc20000862

  日期：——

  Chorinated benzenes (1, 4), biphenyls (6, 9), dibenzofurans (10, 15, 17, 18), 2-chlorodibenzo[1,4]dioxine (24) and 1-chloronaphthalene (26) as well as dibenzofuran (12) and naphthalene (27) themselves were transformed into carboxylic acids by galvanostatic electroreduction in the presence of carbon dioxide ("electrocarboxylation"). Dry DMF was used as solvent, zinc or stainless steel as cathode and magnesium as a sacrificial anode in an undivided cell. Hydrogenation of aromatic rings was not observed. However, reductive addition of two molecules of carbon dioxide to form dihydrodicarboxylic acids, e.g. 22 and 29, occurs in the dibenzofuran and naphthalene series.

  氯苯（1，4），联苯（6，9），二苯并呋喃（10，15，17，18），2-氯二苯并[1,4]二噁英（24）和1-氯萘（26）以及二苯并呋喃（12）和萘（27）本身在存在二氧化碳的条件下通过恒电流电还原转化为羧酸（“电羧化反应”）。干燥DMF被用作溶剂，锌或不锈钢作为阴极，镁作为牺牲阳极在一个不分隔的电池中。芳香环的氢化反应没有观察到。然而，在二苯并呋喃和萘系列中发生两分子二氧化碳还原加成形成二氢二羧酸，例如22和29。