2-bromobenz(5,6)indene | 398128-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromobenz(5,6)indene
• 英文别名: 2-bromo-1H-cyclopenta[b]naphthalene
• CAS: 398128-14-8
• 化学式: C₁₃H₉Br
• 分子量: 245.118
• InChiKey: MTYZKHYKPYWIBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2-bromobenz(5,6)indene 、 2,2’-联苯二硼酸 在 四(三苯基膦)钯 、 四丁基氢氧化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 以66%的产率得到bis(2-benz(5,6)indenyl)biphenyl
  参考文献：
  名称：

  A Suzuki Coupling Based Route to 2,2‘-Bis(2-indenyl)biphenyl Derivatives

  摘要：

  Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-BU)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.

  DOI：

  10.1021/jo016040i
• 作为产物：
  描述：

  2,3-二氢-1H-环戊烷并[B]萘-1-酮 在 sodium tetrahydroborate 、 溴 、 苯基三甲基溴化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 2-bromobenz(5,6)indene
  参考文献：
  名称：

  A Suzuki Coupling Based Route to 2,2‘-Bis(2-indenyl)biphenyl Derivatives

  摘要：

  Because of the promising performance in olefin polymerization of 2,2'-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2'-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2'-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2'-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2'-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-BU)(4)NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.

  DOI：

  10.1021/jo016040i

文献信息

• SUBSTITUTED BIS-2-INDENYL METALLOCENE COMPOUNDS
  申请人：SABIC GLOBAL TECHNOLOGIES B.V.

  公开号：US20210253749A1

  公开（公告）日：2021-08-19

  The present invention provides a compound according to formula (I): (I) wherein: R2 is a bridging moiety containing at least one sp2 hybridised carbon atom; each R4, R4′, R7 and R7′ are hydrogen or moieties comprising 1-10 carbon atoms, wherein each R4, R4′, R7 and R7′ are the same; each R5, R5′, R6 and R6′ are moieties comprising 1-10 carbon atoms, wherein each R5, R5′, R6 and R6′ are the same; and Z is a moiety selected from ZrX 2 , HfX 2 , or TiX 2 , wherein X is selected from the group of halogens, alkyls, aryls and aralkyls. Such compound allows for the preparation of catalyst systems that provide improved olefin reactivity, such as ethylene reactivity, increased molecular weight in olefin polymerisation, such as increased M w in ethylene polymerisation, and increased comonomer incorporation in copolymerisation reactions of olefins, such as in copolymerisation reactions of ethylene with 1-hexene.