dibromobutadiyne | 36333-41-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代乙炔及其衍生物
• 英文名称: dibromobutadiyne
• 英文别名: Dibrom-butadiin；Dibrom-diacetylen；1,4-Dibrombutadiin；Dibromdiacetylen；1,4-dibromobuta-1,3-diyne
• CAS: 36333-41-2
• 化学式: C₄Br₂
• 分子量: 207.852
• InChiKey: WTNKPRUJYFZQFT-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  158.5°C (rough estimate)
• 密度：
  2.4252 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903399090

反应信息

• 作为反应物：
  描述：

  dibromobutadiyne 在 溴 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以36%的产率得到tetrabromobutatriene
  参考文献：
  名称：

  Tetrabromobutatriene:  Completing the Perhalocumulene Series

  摘要：

  Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br-2 at -25 degreesC in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.

  DOI：

  10.1021/ol049734x
• 作为产物：
  描述：

  丁二炔 在 次溴酸钾 作用下， 生成 dibromobutadiyne
  参考文献：
  名称：

  Straus; Kollek; Hauptmann, Chemische Berichte, 1930, vol. 63, p. 1897

  摘要：

  DOI：

文献信息

• Synthesis of the Stable Ordered Conjugated Polymer Poly(dibromodiacetylene) from an Explosive Monomer
  作者：Hongjian Jin、Christopher N. Young、Gary P. Halada、Brian L. Phillips、Nancy S. Goroff

  DOI：10.1002/anie.201504713

  日期：2015.12

  nitrile side groups, in which halogen bonds align the dibromobutadiyne monomers for topochemical polymerization. The cocrystals with the bis(nitrile) oxalamide host undergo complete ordered polymerization to PBDA, demonstrated by solid‐state MAS‐NMR, Raman, and optical absorption spectroscopy. Once formed, the polymer can be separated from the host; unlike the monomer, PBDA is stable at room temperature

  二溴丁二炔是一种极不稳定的化合物，即使在惰性气氛下也能在室温下爆炸。这种不稳定性使对二溴丁二炔的研究几乎完全限于光谱表征。在这里，我们报告了一种通过共晶中的拓扑化学反应来控制二溴丁二炔反应性的方法，从而导致了有序的聚合物聚（二溴二乙炔），PBDA。在低温（−15至-18°C）下，二溴丁二炔可与含有吡啶基或腈侧基的草酰胺主体分子形成共晶体，其中卤素键使二溴丁二炔单体排列成拓扑化学聚合反应。固态MAS-NMR，拉曼光谱和光学吸收光谱证明，与双（腈）草酰胺共晶体共完成有序聚合成PBDA。一旦形成，聚合物可以与主体分离；与单体不同，PBDA在室温下稳定。
• DE495787
  申请人：——

  公开号：——

  公开（公告）日：——
• A Step-Growth Approach to Metal-Capped One-Dimensional Carbon Allotropes: Syntheses of C12, C16, and C20μ-Polyynediyl Complexes
  作者：Tamás Bartik、Berit Bartik、Monika Brady、Roman Dembinski、J. A. Gladysz

  DOI：10.1002/anie.199604141

  日期：1996.3.1
• Toward Metal-Capped One-Dimensional Carbon Allotropes:  Wirelike C₆−C₂₀ Polyynediyl Chains That Span Two Redox-Active (η⁵-C₅Me₅)Re(NO)(PPh₃) Endgroups
  作者：Roman Dembinski、Tamás Bartik、Berit Bartik、Monika Jaeger、J. A. Gladysz

  DOI：10.1021/ja992747z

  日期：2000.2.1

  Reaction of the butadiynyl complex (eta(5)-C5Me5)Re(No)(PPh3)(C drop CC drop CH) (ReC4H) with Cu(OAc)(2) (pyridine, 80 degrees C) gives the mu-octatetraynediyl complex ReC8Re (70%). Analogous cross-coupling of ReC4H and ReC2H gives (after chromatography) ReC4Re (14%), ReC6Re (44%), and ReC8Re (15%). Longer sp carbon chains are accessed by reactions of ReC4H with n-BuLi and CuI, which give ReC4Cu. This isolable species is treated in situ with BrC drop CSiEt3 or BrC drop CC drop CSiMe3 (excess EtNH2, THF) to give ReC6SiEt3 or ReC8SiMe3 (84-77%). Desilylations (wet n-Bu4N+F-) yield ReC6H or ReC8H (88-73%). Then Cu(OAc)(2) (pyridine, 50 degrees C) gives ReC12Re or ReC16Re (71-67%). The former is also available from ReC4Cu and BrC drop CC drop CBr (45%), and ReC10Re can be accessed by cross-coupling. ReC6H and ReC8H are similarly converted to ReC10SiR3 (R = Me, Et; 51-26%) and ReC12SiMe3 (43%). Desilylation of ReC10SiR3 gives labile ReC10H, but only black powder is obtained from ReC12SiMe3. In situ coupling of ReC10H gives ReC20Re (52-34%), which unlike lower homologues is not obtained in analytically pure form. The effects of chain length upon visible spectra (progressively red-shifted and more intense bands; epsilon > 190 000 M-1 cm(-1)), IR/ Raman nu(C drop C) patterns (progressively more bands),C-13 NMR chemical shifts (asymptotic limit of 64-67 ppm for ReC drop C((C) under bar drop (C) under bar)(n)), cyclic voltammetry (decreased reversibility of two oxidations; a gradual shift of the first to thermodynamically less favorable potentials, so that only a single oxidation is observed for ReC20Re), and thermal stabilities (solid-state decompositions at 155 degrees C, ReC20Re, and 178-217 degrees C, lower homologues) are studied in detail.