1,3,5-benzenetrisulfonyl fluoride | 368-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-benzenetrisulfonyl fluoride
• 英文别名: 1,3,5-tris(fluorosulfonyl)benzene；benzene-1,3,5-trisulfonyl fluoride；Benzol-1,3,5-trisulfonylfluorid
• CAS: 368-65-0
• 化学式: C₆H₃F₃O₆S₃
• 分子量: 324.279
• InChiKey: PBBSHDQCHWQIJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  166-167 °C
• 沸点：
  427.0±40.0 °C(Predicted)
• 密度：
  1.785±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-benzenetrisulfonyl fluoride 在 sodium sulfite 作用下， 以 氘代二甲亚砜 、 水 为溶剂， 生成
  参考文献：
  名称：

  1,3,5-三（氟磺酰基）苯的阴离子σ络合物

  摘要：

  我们已经发现，对称的苯三磺酸三氟化物1能够在芳环的自由位置进行亲核加成。其与亚硫酸钠，吗啉反应和丙二酸和乙酰乙酸酯，双甲酮和硝基甲烷导致相对稳定的阴离子σ-复合物的形成的碳负离子3 - 8。

  DOI：

  10.1016/j.tetlet.2008.02.151
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium fluoride 、 水 、 xylene 作用下， 生成 1,3,5-benzenetrisulfonyl fluoride
  参考文献：
  名称：

  CCLXXXVI。—芳族磺酰氟。一种方便的制备方法

  摘要：

  DOI：

  10.1039/jr9310002104

文献信息

• Process for the preparation of fluorinated benzene sulfonyl fluorides
  申请人：Allied-Signal Inc.

  公开号：US04886629A1

  公开（公告）日：1989-12-12

  The present invention relates to a process for the preparation of a fluorinated benzene sulfonyl fluoride comprising the step of: heating a benzene sulfonyl fluoride of the Formula (I) ##STR1## where Y is fluorine, chlorine, bromine, iodine, a methyl group, an ethyl group, or a propyl group; p is 0 to 3; and q is 2 to 6, in the presence of an alkali metal fluoride under conditions and for a time sufficient to provide a fluorinated benzene sulfonyl fluoride of the Formula (II) ##STR2## where x is 1 to 5; m=q-x; and Y and p are as defined above. The present invention also provides novel benzene sulfonyl fluorides of the Formula (III) ##STR3## where each Y is meta or para to --SO.sub.2 F and is independently selected from the group consisting of chlorine, fluorine, fluorosulfonyl, methyl group, ethyl group, and propyl group; and p is 1 or 2. The fluorinated benzene sulfonyl fluorides are versatile fluorinated intermediates. They are readily converted to sulfonamides of potential activity, or the sulfonyl group can be converted into another functional group, or removed to provide fluorinated benzenes.

  本发明涉及一种制备氟代苯磺酰氟的方法，包括以下步骤：在碱金属氟的存在下，加热具有化学式（I）的苯磺酰氟 ##STR1## 其中，Y为氟、氯、溴、碘、甲基基团、乙基基团或丙基基团；p为0至3；q为2至6，条件和时间足以提供具有化学式（II）的氟代苯磺酰氟 ##STR2## 其中，x为1至5；m=q-x；Y和p如上所定义。本发明还提供具有化学式（III）的新型苯磺酰氟 ##STR3## 其中，每个Y都为对位或间位于--SO.sub.2 F，独立选择自氯、氟、氟磺酰、甲基基团、乙基基团和丙基基团；p为1或2。氟代苯磺酰氟是多功能的氟代中间体。它们可以轻松转化为具有潜在活性的磺酰胺，或者磺酰基可以转化为另一种功能基团，或者去除以提供氟代苯。
• [EN] POLYMERIZATION OF SILYL- AND FLUORO-CONTAINING MONOMERS<br/>[FR] POLYMÉRISATION DE MONOMÈRES CONTENANT DU FLUOR ET DU SILYLE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2016209920A1

  公开（公告）日：2016-12-29

  Condensation of fluoro-substituted and silyl-substituted monomers provides polymers suitable for use, e.g., as engineering polymers. A monomer composition is condensed in the presence of a bifluoride or poly(hydrogen fluoride) fluoride salt. The monomer composition contains a compound of formula F-X-F and a compound of formula (R1)3Si-Z-Si(R1)3, and forms an alternating X-Z polymer chain and a silyl fluoride byproduct. X has the formula -A(-R2-A)n -; each A is SO2, C(=O), or Het; R2 is an organic moiety; n is 0 or 1; Het is an aromatic nitrogen heterocycle; Z has the formula -L-R3-L-; each L is O, S, or N(R4); and each R3 is an organic moiety, and R4 comprises H or an organic moiety.

  氟取代和硅取代单体的缩聚提供了适用于工程聚合物的聚合物。在双氟化物或聚(氢氟酸)氟盐存在下缩聚单体组成物。单体组成物包含化合物F-X-F的公式和化合物(R1)3Si-Z-Si(R1)3的公式，并形成交替的X-Z聚合物链和一个硅氟化物副产物。X具有公式-A(-R2-A)n-；每个A是SO2，C(=O)或Het；R2是一个有机基团；n为0或1；Het是芳香族氮杂环；Z具有公式-L-R3-L-；每个L是O，S或N(R4)；每个R3是一个有机基团，R4包括H或一个有机基团。
• Interaction of 2,4,6-tris(fluorosulfonyl)chlorobenzene with O-, N-, S-, C-nucleophiles and F-anion
  作者：Andrey A. Filatov、Vladimir N. Boiko、Yurii L. Yagupolskii

  DOI：10.1016/j.jfluchem.2012.05.015

  日期：2012.11

  Reactions of 2,4,6-tris(fluorosulfonyl)chlorobenzene 1 with O-, N-, S-, C-nucleophiles and F-anion showed high reactivity of 1 that was defined by three strong electron withdrawing SO2F groups creating several electrophilic centers within the molecule. Conditions for selective chlorine atom substitution were defined that resulted in formation of corresponding ethers, amines and sulfides, while excess

  2,4,6-三（氟磺酰基）氯苯1与O-，N-，S-，C-亲核试剂和F-阴离子的反应显示1的高反应性，这由三个强吸电子SO 2 F基团定义分子内的亲电中心。定义了选择性氯原子取代的条件，该条件导致形成相应的醚，胺和硫化物，而亲核试剂的过量通常导致反应中涉及SO 2 F基团。两当量的氟阴离子源不仅引起氯-氟取代，而且还导致了在hem位具有两个氟原子的阴离子σ络合物的形成。还原氯苯1 发现用锌/ AcOH制备1,3,5-三（氟磺酰基）苯是一种选择。
• Reactions of 1,3,5-tris(fluorosulfonyl)benzene with some nucleophilic reagents
  作者：Oksana M. Kamoshenkova、Vladimir N. Boiko

  DOI：10.1016/j.jfluchem.2009.11.019

  日期：2010.2

  The reactions of 1,3,5-tris(fluorosulfonyl)benzene 1 with nucleophilic agents were investigated. It was found that morpholine, β,β,β-trifluoroethanol in the presence of triethylamine and sodium azide formed corresponding 1,3,5-trisulfonyl derivatives. In contrast, nucleophiles such as aniline, thiourea, and potassium thiocyanate do not react with compound 1 even in excess and under moderate heating

  研究了1,3,5-三（氟磺酰基）苯1与亲核试剂的反应。发现在三乙胺和叠氮化钠存在下吗啉，β，β，β-三氟乙醇形成相应的1,3,5-三磺酰基衍生物。相反，亲核试剂例如苯胺，硫脲和硫氰酸钾即使在过量和适度加热下也不与化合物1反应。发现了在三乙胺存在下，一个SO 2 F基团被吗啉，DMAP和苯胺选择性取代氟原子的条件，以及两个SO 2 F基团被DMAP选择性取代的条件。分离出化合物1与硝基甲烷的阴离子σ-络合物，作为单独的化合物。
• POLYMERIZATION METHOD AND POLYMERS FORMED THEREWITH
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20150315340A1

  公开（公告）日：2015-11-05

  Condensation of fluoro-substituted and silyl-substituted monomers provides polymers suitable for use, e.g., as engineering polymers. A monomer composition is condensed in the presence of a basic catalyst. The monomer composition contains a compound of formula F—X—F and a compound of formula (R 1 )3Si—Z—Si(R 1 )3, and forms an alternating X—Z polymer chain and a silyl fluoride byproduct. X has the formula -A(-R 2 -A)n-; each A is SO 2 , C(═O), or Het; R 2 is an organic moiety; n is 0 or 1; Het is an aromatic nitrogen heterocycle; Z has the formula -L-R 3 -L-; each L is O, S, or N(R 4 ); and each R 3 is an organic moiety, and R 4 comprises H or an organic moiety.

  含氟和硅烷取代单体的聚合物可以作为工程聚合物使用。在碱性催化剂的存在下，将单体组合物进行缩合反应。单体组合物包含化合物F—X—F和化合物(R1)3Si—Z—Si(R1)3，并形成交替的X—Z聚合物链和硅氟化物副产物。X的公式为-A(-R2-A)n-；每个A是SO2，C(═O)或Het；R2是有机基团；n为0或1；Het是芳香族氮杂环；Z的公式为-L-R3-L-；每个L是O，S或N(R4)；每个R3是有机基团，R4包括H或有机基团。