2-(4-甲基苯基)磺酰苯酚 | 10371-01-4

• 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-(4-甲基苯基)磺酰苯酚
• 英文名称: 2-[(4-methylphenyl)sulfonyl]phenol
• 英文别名: 2-hydroxyphenyl-p-toluenesulfonate；2-hydroxyphenyl p-tolyl sulphone；2-hydroxyphenyl 4-tolyl sulfone；2-(toluene-4-sulfonyl)-phenol；2-(Toluol-4-sulfonyl)-phenol；(2-Hydroxy-phenyl)-p-tolyl-sulfon；Phenol, 2-[(4-methylphenyl)sulfonyl]-；2-(4-methylphenyl)sulfonylphenol
• CAS: 10371-01-4
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: GRNCNZGRNOWBKC-UHFFFAOYSA-N

物化性质

• 熔点：
  126-127 °C(Solv: ethanol (64-17-5))
• 沸点：
  430.2±38.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯基)磺酰苯酚 、 硫酸二甲酯 在 sodium hydroxide 作用下， 生成 1-methoxy-2-tosylbenzene
  参考文献：
  名称：

  Amin et al., Journal Of Scientific and Industrial Research, 1954, vol. 13 B, p. 181

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铝 作用下， 生成 2-(4-甲基苯基)磺酰苯酚
  参考文献：
  名称：

  DE532403

  摘要：

  公开号：

文献信息

• Graphite/Methanesulfonic Acid (GMA) as a New Reagent for Sulfonylation of Phenols and Thia-Fries Rearrangement of Aryl Sulfonates to Sulfonylphenols
  作者：Hashem Sharghi、Zahra Shahsavari-Fard

  DOI：10.1002/hlca.200490295

  日期：2005.1

  A new facile method for direct sulfonylation of phenols was developed. Graphite in methanesulfonic acid (GMA) was used to prepare sulfonylphenols by sulfonylation of phenol and naphthalene derivatives with p-toluenesulfonic acid (=4-methylbenzenesulfonic acid) (Table 1) and the thia-Fries rearrangement of aryl sulfonates (Table 4). Mechanistic studies showed that the sulfonylation reaction of phenols

  开发了一种新的直接苯酚磺酰化的简便方法。使用甲磺酸中的石墨（GMA）通过苯酚和萘衍生物与对甲苯磺酸（= 4-甲基苯磺酸）（表1）进行磺酰化以及芳基磺酸盐的硫-弗里斯重排（表4）来制备磺酰基苯酚。机理研究表明，GMA中苯酚的磺酰化反应是通过最初的磺酸盐形成，然后通过分子间机理使芳基磺酸盐的硫-弗里斯重排而发生的（方案3）。
• Regioselectivity control of radiation-induced reaction: electron beam-induced Fries rearrangement of sulfonamide within a β-cyclodextrin inclusion complex
  作者：Jun Kato、Hiroyuki Kakehata、Yasunari Maekawa、Takashi Yamashita

  DOI：10.1039/b606689e

  日期：——

  EB (electron beam) irradiation of sulfonamide within a β-cyclodextrin (β-CD) inclusion complex in the solid state induced the solvent-free Fries rearrangement, which proceeded at a shorter reaction time with reversed regioselectivity by inclusion into the β-CD, compared with that of sulfonamide crystals; the β-CD as a restricted nanospace had a large effect on the reactivity and regioselectivity of the solvent-free EB-Fries rearrangement.

  在固态下，δ-环糊精（δ-CD）包合复合物中的磺酰胺经电子束（EB）辐照后可诱导无溶剂弗里斯重排，与磺酰胺晶体相比，包合到δ-CD中的磺酰胺重排反应时间更短，且具有反向区域选择性；作为受限纳米空间的δ-CD对无溶剂EB-弗里斯重排的反应活性和区域选择性有很大影响。
• Aromatic Sulfonylation. II. Attacking Species under Various Conditions.
  作者：Yoshio Kohara、Michio Kobayashi、Hiroshi Minato

  DOI：10.1246/bcsj.43.520

  日期：1970.2

  p-Toluenesulfonylation of toluene and anisole in the presence of AlCl3, SbCl5 or TiCl4 was investigated in methylene chloride, nitromethane and nitrobenzene. Substitution took place at 8.6–13.4% and 86.6–91.4% para positions for toluene in methylene chloride, but 42.0–45.7% ortho and 54.2–58.0% para isomers were obtained in nitromethane and nitrobenzene. Sulfonylation of toluene with p-CH3C6H4SO2+ ClO4− afforded 44.8–46.3% ortho and 53.7–55.2% para isomers. Partial rate factors for toluene were pf=52.5 in methylene chloride, of=12.6±0.9, pf=31.4±2.0 in nitromethane, and of=16.0±1.7, pf=38.3±4.2 with p-CH3C4H4SO2+ClO4−. A plausible mechanism is proposed, in which the attacking species is TsCl-MCln complex in methylene chloride, but it is an ion pair, ArSO2+MCl−n+1, in nitromethane and nitrobenzene.

  研究了在二氯甲烷、硝基甲烷和硝基苯中，AlCl3、SbCl5 或 TiCl4 存在下甲苯和苯甲醚的对甲苯磺酰化反应。在二氯甲烷中，甲苯在 8.6-13.4% 的位置和 86.6-91.4% 的对位位置发生了取代，但在硝基甲烷和硝基苯中得到了 42.0-45.7% 的正异构体和 54.2-58.0% 的对位异构体。用 p-CH3C6H4SO2+ ClO4- 对甲苯进行磺化，可得到 44.8-46.3% 的正异构体和 53.7-55.2% 的对位异构体。甲苯在二氯甲烷中的部分速率因子为 pf=52.5，在硝基甲烷中为 of=12.6±0.9，pf=31.4±2.0，在 p-CH3C4H4SO2+ClO4- 中为 of=16.0±1.7，pf=38.3±4.2。提出了一种可信的机理，即在二氯甲烷中，攻击物种是 TsCl-MCln 复合物，但在硝基甲烷和硝基苯中，攻击物种是离子对 ArSO2+MCl-n+1。
• Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds
  作者：Ngoc-Lan Thi Nguyen、Quoc-Anh Nguyen、Tien Khoa Le、Thi Xuan Thi Luu、Kim-Ngan Thi Tran、Phuoc-Bao Pham

  DOI：10.3390/molecules27051644

  日期：——

  Chloroaluminate ionic liquid bound on magnetic nanoparticles (Fe3O4@O2Si[PrMIM]Cl·AlCl3) was prepared and used as a heterogenous Lewis acidic catalyst for the Friedel–Crafts sulfonylation of aromatic compounds with sulfonyl chlorides or p-toluenesulfonic anhydride. The catalyst’s stability, efficiency, easy recovery, and high recyclability without considerable loss of catalytic capability after four recycles

  制备了结合在磁性纳米颗粒上的氯铝酸盐离子液体（Fe3O4@O2Si[PrMIM]Cl·AlCl3），并将其用作多相路易斯酸性催化剂，用于芳族化合物与磺酰氯或对甲苯磺酸酐的傅克磺酰化反应。该催化剂的稳定性、效率、易回收性和高可循环性在四次循环后催化能力没有明显损失是其优势的证明。此外，化学计量比、底物范围广、反应时间短、砜类收率高和无溶剂反应条件也使该方法实用、环保和经济。
• COLOR DEVELOPING COMPOSITION CONTAINING MOLECULAR COMPOUND, AND RECORDING MATERIAL
  申请人：Kodama Satoshi

  公开号：US20110120345A1

  公开（公告）日：2011-05-26

  Provided is a color-developing composition containing a molecular compound which has as a component compound a compound represented by formula (I) [wherein Y represents a C1-C12 hydrocarbon group which is chained or branched and saturated or unsaturated, or a C1-C8 hydrocarbon group which is chained or branched, saturated or unsaturated and has an ether or thioether bond; R 1 , R 2 , R 3 and R 4 each independently represent a C1-C6 alkyl group or C2-C6 alkenyl group; n, p, q and r each represents any integer of 0 to 4; and m represents any integer of 0 to 2]. Also provided is a recording material with a sufficient color-forming sensitivity, superior storage stability, and especially with an extremely little background fogging in a heat resistance test.

  提供的是一种含有分子化合物的彩色显影组合物，该分子化合物的组分包括由式（I）表示的化合物[其中Y表示链状或支链的C1-C12烃基，饱和或不饱和，或链状或支链的C1-C8烃基，饱和或不饱和，且具有醚或硫醚键；R1、R2、R3和R4各自独立地表示C1-C6烷基或C2-C6烯基；n、p、q和r各自表示0至4的任意整数；m表示0至2的任意整数]。还提供了一种具有足够的显色敏感性、优异的储存稳定性，特别是在耐热性测试中具有极少背景雾化的记录材料。