1-{[bromo(difluoro)methyl]sulfanyl}-4-chlorobenzenenzene | 78840-52-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-{[bromo(difluoro)methyl]sulfanyl}-4-chlorobenzenenzene
• 英文别名: 1-chloro-4-(bromodifluoromethylsulfanyl)benzene；bromodifluoro(4-chlorophenylthio)methane；1-[Bromo(difluoro)methyl]sulfanyl-4-chlorobenzene
• CAS: 78840-52-5
• 化学式: C₇H₄BrClF₂S
• 分子量: 273.529
• InChiKey: CMTHFPOINZWVJE-UHFFFAOYSA-N

物化性质

• 沸点：
  195.4±40.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{[bromo(difluoro)methyl]sulfanyl}-4-chlorobenzenenzene 在 silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到对氯三氟甲基苯硫醚
  参考文献：
  名称：

  ¹⁸ F‐Labeling of Aryl‐SCF ₃ , ‐OCF ₃ and ‐OCHF ₂ with [ ¹⁸ F]Fluoride

  摘要：

  AbstractWe report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic 18F‐fluorination of aryl‐OCHFCl, ‐OCF2Br and ‐SCF2Br precursors under mild conditions. This AgI‐mediated process allows for the first time access to a range of 18F‐labeled aryl‐OCHF2, ‐OCF3 and ‐SCF3 derivatives, inclusive of [18F]riluzole. The 18F‐labeling of these medicinally important motifs expands the radiochemical space available for PET applications.

  DOI：

  10.1002/anie.201504665
• 作为产物：
  描述：

  二溴二氟甲烷 、 4-氯苯硫酚 在 sodium hydride 作用下， 生成 1-{[bromo(difluoro)methyl]sulfanyl}-4-chlorobenzenenzene
  参考文献：
  名称：

  溴二氟甲基硫化物的制备及其转化为三氟甲基硫化物

  摘要：

  溴二氟甲基硫化物是通过硫醇盐与CF 2 BrX（x = Br，Cl）反应制得的。用各种无机氟化物处理溴代二氟甲基硫化物可制得三氟甲基硫化物。

  DOI：

  10.1016/s0040-4039(01)92888-6

文献信息

• New preparation of difluoroiodomethylsulfanylbenzenes and their radical addition to unsaturated compounds initiated by sodium dithionite
  作者：Xueyan Yang、Xiang Fang、Xianjin Yang、Min Zhao、Yizheng Han、Yongjia Shen、Fanhong Wu

  DOI：10.1016/j.tet.2007.12.018

  日期：2008.2

  Difluoroiodomethylsulfanylbenzene (3a) and 1-chloro-4-difluoroiodomethylsulfanylbenzene (3b) are novel and efficient difluoromethylating reagents via the reaction with unsaturated compounds, such as alkenes, ethynylbenzene, pent-4-en-1-ols, and pent-4-enoic acids initiated by Na2S2O4, to afford the corresponding adducts, tetrahydrofuran derivatives, and γ-butyrolactones containing difluoromethylene

  二氟碘甲基硫烷基苯（3a）和1-氯-4-二氟碘甲基硫烷基苯（3b）是通过与不饱和化合物（如烯烃，乙炔基苯，戊-4-烯-1-醇和戊-4-烯醇）反应而形成的新型高效二氟甲基化试剂。由Na 2 S 2 O 4引发的酸，以中等至良好的产率得到相应的加合物，四氢呋喃衍生物和含二氟亚甲基的γ-丁内酯。
• AIBN-initiated radical addition of gem-difluorinated alkyl iodides to alkynes and the Pd-catalyzed Sonogashira coupling reaction of E-phenyl difluoromethylene vinylic iodides with terminal alkynes
  作者：Xiang Fang、Xueyan Yang、Xianjin Yang、Shenjie Mao、Zhonghua Wang、Guorong Chen、Fanhong Wu

  DOI：10.1016/j.tet.2007.07.087

  日期：2007.10

  The addition of gem-difluorinated alkyl iodides to alkynes initiated by AIBN neatly gave the corresponding difluoromethylene vinyl iodides among which the stereoselectivity of aromatic acetylenes was high. The further coupling reaction of E-phenyl difluoromethylene vinyl iodides with terminal alkynes in the presence of catalytic palladium afforded the substituted difluorinated enynes.

  加入宝石-difluorinated烷基碘于由AIBN引发炔整齐，得到相应的二氟亚甲基乙烯基碘化物其中芳族乙炔的立体选择性是很高的。在催化钯的存在下，E-苯基二氟亚甲基乙烯基碘与末端炔的进一步偶联反应得到取代的二氟烯。
• Visible-Light-Induced Difunctionalization of 3-Butenoic Acid with Bromodifluoromethyl Heteroarylsulfones
  作者：Qianqian Liu、Xiaoping Wang、Xuefeng Gu、Huiming Dai、Zhibin Huang、Yingsheng Zhao

  DOI：10.1021/acs.orglett.4c02277

  日期：2024.8.2

  a visible-light-induced iridium-promoted direct bifunctionalization of 3-butenoic acid with bromodifluoromethyl heteroarylsulfones. This methodology enables the concurrent introduction of difluoromethyl heteroarylsulfone and bromine groups into 3-butenoic acid under mild reaction conditions. Various α-substituted 3-butenoic acids and bromodifluoromethyl heteroarylsulfones were found to be compatible

  在此，我们报道了可见光诱导的铱促进的 3-丁烯酸与溴二氟甲基杂芳基砜的直接双官能化。该方法能够在温和的反应条件下将二氟甲基杂芳基砜和溴基团同时引入3-丁烯酸中。各种α-取代的3-丁烯酸和溴二氟甲基杂芳基砜被发现是相容的，以中等至良好的收率产生相应的产物。该方法为氟代羧酸衍生物的合成开辟了一条新路线。
• A Convergent Route to Geminal Difluorosulfides and to Functionalized Difluorothiochromans, a New Family of Organofluorine Compounds
  作者：Pierre Salomon、Samir Z. Zard

  DOI：10.1021/ol5002939

  日期：2014.3.7

  The synthesis of the novel O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate and its radical addition to various terminal alkenes are described. The geminal difluorosulfide adducts undergo closure onto the aromatic ring by further treatment with peroxide to furnish difluorothiochromans, a new family of organofluorine compounds.
• Electrophilic Difluoro(phenylthio)methylation: Generation, Stability, and Reactivity of α-Fluorocarbocations
  作者：Nolan M. Betterley、Panida Surawatanawong、Samran Prabpai、Palangpon Kongsaeree、Chutima Kuhakarn、Manat Pohmakotr、Vichai Reutrakul

  DOI：10.1021/ol402631t

  日期：2013.11.15

  Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of alpha-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+).