4-溴-4’-甲基联苯 | 50670-49-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 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: 4-溴-4’-甲基联苯
• 中文别名: 4-溴-4'-甲基联苯
• 英文名称: 4-bromo-4'-methylbiphenyl
• 英文别名: 4-bromo-4'-methyl-1,1'-biphenyl；4-bromo-4′-methylbiphenyl；4-bromo-4’-methylbiphenyl；4-methyl-4'-bromo-biphenyl；1-bromo-4-(4-methylphenyl)benzene
• CAS: 50670-49-0
• 化学式: C₁₃H₁₁Br
• 分子量: 247.134
• InChiKey: MYWLXURJCXISCT-UHFFFAOYSA-N

物化性质

• 熔点：
  136℃
• 沸点：
  314-315 °C
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2903999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-溴-4’-甲基联苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 0.25h， 生成 4-bromo-4'-(bromomethyl)-1,1'-biphenyl
  参考文献：
  名称：

  Conformationally restricted retinoids

  摘要：

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.

  DOI：

  10.1021/jm00377a022
• 作为产物：
  描述：

  1-溴-4-[4-(三氟甲基)苯基]苯 在 三乙基硅烷 、 四氯化钛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以83%的产率得到4-溴-4’-甲基联苯
  参考文献：
  名称：

  氢化钛催化四氯化钛催化加氢脱氟引发的三氟甲苯的转化

  摘要：

  以三乙基硅烷为还原剂，开发了四氯化钛催化的三氟甲苯衍生物的加氢脱氟反应。该反应通过容易获得的试剂产生了具有高化学选择性的各种甲苯衍生物。这种加氢脱氟过程已扩展到分子内Friedel-Crafts苄基化反应，从而以良好的收率提供了各种环大小的多环芳族化合物。

  DOI：

  10.1002/adsc.201500920

文献信息

• Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance
  作者：Szilvia Bunda、Krisztina Voronova、Ágnes Kathó、Antal Udvardy、Ferenc Joó

  DOI：10.3390/molecules25173993

  日期：——

  salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2−. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved

  水溶性的 salan 配体是通过对具有连接氮原子的各种桥接单元（接头）的 salens（N，N'-双（亚硅基）乙二胺和类似物）进行氢化和随后的磺化来合成的。Pd (II) 配合物是在硫柳胺和 [PdCl4]2- 的反应中获得的。配体和配合物的表征也包括广泛的 X 射线衍射研究。Pd (II) 配合物被证明是芳基卤化物和芳基硼​​酸衍生物在 80°C 下在水和空气中的 Suzuki-Miyaura 反应的高活性催化剂。对 Pd (II)-磺胺嘧啶催化剂的比较研究表明，催化活性随着接头长度的增加和配体 N 供体原子周围空间拥挤度的增加而大大增加；最高比活为40,000（mol底物）（mol催化剂×h）-1。
• Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction
  作者：Yongxin Han、Shawn D Walker、Robert N Young

  DOI：10.1016/0040-4039(96)00364-4

  日期：1996.4

  A method for attaching haloarylsilanes to polymer support was developed. The polymer bound arylhalides were reacted with a variety of ArB(OH)2 under the Suzuki cross-coupling reaction conditions and the coupled resins were cleaved by different electrophiles to give ipso-substitution products in good yields.

  开发了一种将卤代芳基硅烷连接到聚合物载体上的方法。在Suzuki交叉偶联反应条件下，使聚合物键合的芳基卤化物与各种ArB（OH）2反应，并通过不同的亲电试剂裂解偶联的树脂，从而以高收率得到ipso取代产物。
• Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
  作者：Hongyin Gao、Zhe Zhou、Doo-Hyun Kwon、James Coombs、Steven Jones、Nicole Erin Behnke、Daniel H. Ess、László Kürti

  DOI：10.1038/nchem.2672

  日期：2017.7

  Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C−C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (−NH2) and hydroxyl (−OH) groups to arylmetals in a scalable and environmentally

  芳基金属是非常有价值的碳亲核体，可以容易地和廉价地从芳基卤化物或芳烃制得，并且广泛用于实验室和工业规模以直接与各种亲电体反应。尽管CC键的形成一直是有机合成的主要内容，但是由于缺乏氨基，伯氨基（-NH 2）和羟基（-OH）以可扩展且对环境友好的方式直接转移至芳基金属仍然是一项艰巨的合成挑战。合适的杂原子转移试剂。在这里，我们演示了基准稳定的NH和N的使用衍生自易于获得的类萜骨架的-烷基恶唑烷，作为有效的多功能试剂，可用于结构多样的芳基和杂芳基金属的直接伯胺化和羟基化。这种实用且可扩展的方法可在低温下一步一步合成伯胺和苯酚，并且避免使用过渡金属催化剂，配体和添加剂，氮保护基，过量的试剂和苛刻的后处理条件。
• Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
  作者：Mincong Su、Xia Huang、Chuanhu Lei、Jian Jin

  DOI：10.1021/acs.orglett.1c04018

  日期：2022.1.14

  nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used

  已经使用（杂）芳基溴化物和乙酸乙烯酯作为偶联伙伴实现了镍催化的还原交叉偶联。这种温和、适用的方法提供了获得各种乙烯基芳烃、杂芳烃和苯并杂环化合物的可靠途径，这将扩大精细化学品和聚合物前体的化学空间。重要的是，使用了一种可持续溶剂二甲基异山梨醇，从绿色化学的角度来看，这使得该协议更具吸引力。
• 5-HYDROXYPYRIMIDINE-4-CARBOXAMIDE COMPOUND
  申请人：Kuribayashi Takeshi

  公开号：US20110112103A1

  公开（公告）日：2011-05-12

  The present invention provides compounds which promote erythropoietin production. Compounds represented by the following general formula (1) or pharmacologically acceptable salts thereof are provided: [wherein, R 1 represents a group —X-Q 1 , X-Q 1 -Y-Q 2 or X-Q 1 -Y-Q 2 -Z-Q 3 , X represents a single bond, —CH 2 — or the like, Q 1 represents a monocyclic or bicyclic heterocyclic group which may have substituent(s), Y represents a single bond, —CH 2 —, or the like, Q 2 represents a monocyclic or bicyclic hydrocarbon ring group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), Z represents a single bond, —CR 11 R 12 — or the like, R 11 and R 12 each independently represents a hydrogen atom, a halogen atom or the like, Q 3 represents a phenyl group which may have substituent(s), a C 3 -C 7 cycloalkyl group which may have substituent(s), a C 3 -C 7 cycloalkenyl group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), R 2 represents a C 1 -C 3 alkyl group or the like, and R 3 represents a hydrogen atom or a methyl group].

  本发明提供促进促红细胞生成素产生的化合物。提供以下一般式（1）表示的化合物或其药理学上可接受的盐： [其中，R 1 表示一个基团-X-Q 1 ，X-Q 1 -Y-Q 2 或X-Q 1 -Y-Q 2 -Z-Q 3 ，X表示一个单键，-CH 2 -或类似物，Q 1 表示可能具有取代基的单环或双环杂环基团，Y表示一个单键，-CH 2 -或类似物，Q 2 表示可能具有取代基的单环或双环碳氢环基团或可能具有取代基的单环或双环杂环基团，Z表示一个单键，-CR 11 R 12 -或类似物，R 11 和R 12 各自独立地表示氢原子、卤素原子或类似物，Q 3 表示可能具有取代基的苯基团，可能具有取代基的C 3 -C 7 环烷基团，可能具有取代基的C 3 -C 7 环烯基团或可能具有取代基的单环或双环杂环基团，R 2 表示C 1 -C 3 烷基团或类似物，R 3 表示氢原子或甲基基团]。

表征谱图