1-溴-2-氯乙炔 | 25604-70-0

• 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
• 中文名称: 1-溴-2-氯乙炔
• 英文名称: Bromchloracetylen
• 英文别名: Bromochloroacetylene；1-bromo-2-chloroethyne
• CAS: 25604-70-0
• 化学式: C₂BrCl
• 分子量: 139.379
• InChiKey: MTFOKIURMVQHRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  4
• 可旋转键数：
  0
• 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

反应信息

• 作为反应物：
  描述：

  二茂铁 、 1-溴-2-氯乙炔 在 AlCl₃ 作用下， 以 二氯甲烷 为溶剂， 以13.5%的产率得到1-ferrocenyl-2-bromoacetylene
  参考文献：
  名称：

  Chemical routes to fine tuning the redox potential of monolayers covalently attached on H–Si(100)

  摘要：

  A closely related series of three ferrocene derivatives, bearing a short carbon-carbon tethering arm for covalent attachment to H-terminated Si(1 0 0). has been used to produce electroactive hybrid materials. Three different grafting procedures have been applied for the first time on this type of molecules in order to obtain the full series of possible unsaturations in the C-C lateral chain bound to Si: ethyl, vinyl and ethynyl group, respectively, associated with the surface species (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-CH2-CH2-Si (EtFC/Si), (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-CH=CH-Si (VFC/Si), and (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-C C-Si (EFC/Si).The surface reactions here applied involve Grignard derivatization, Lewis acid catalysis and nucleophilic substitution by an acetylide anion. The redox potentials of the three molecule/surface hybrids, measured by cyclic voltammetry, are 0.059, 0.136 and 0.251 V vs. Ag/Ag+, respectively, from EtFC/Si to EFC/Si and are supposedly following the increasing trend of the extent of unsaturation in the tethering arm. The above trend in redox potentials parallels the one experimentally found and theoretically reproduced for the corresponding isolated molecules, which shows that the adopted functionalization procedures may be used to control the number of residual unsaturations in the C-C arm. The presence and chemical nature of the redox species covalently attached to Si are strongly supported after evaluation of XPS spectra and electrochemical data. The formation of electroactive hybrids on Si with tuneable well-defined switching potentials can be highly beneficial to the development of Si-based memory devices. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2010.05.009
• 作为产物：
  描述：

  Squaric acid bromidechloride 700.0 ℃ 、0.1 Pa 条件下， 生成 1-溴-2-氯乙炔
  参考文献：
  名称：

  Squaric acid difluoride

  摘要：

  Hitherto unknown squaric acid difluoride (3,4-difluoro-3-cyclobutene-1,2-dione) (1a) has been synthesized in 71% yield by gas phase fluorination of squaric acid dichloride (1c) with KF at 250 degrees C. (1a) has been characterized by multinuclear NMR, mass, IR and Raman spectra. The IR spectrum is in excellent agreement with its ab initio prediction (MP2, 6-311 + G(2d, p)). The vacuum thermolysis of (1a) at 700 degrees C does not yield the expected decarbonylation product FCCF (2a) although the precursor of the latter, F2CCCO, and three C3F4 isomers (propyne, allene, cyclopropene) which are also found as decomposition products of (2a) have been identified. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00138-4

文献信息

• Decomposition of [NiRR′L2] complexes induced by bromine or anodic oxidation
  作者：Juan M. Coronas、Guillermo Muller、Mercedes Rocamora

  DOI：10.1016/0022-328x(86)80013-4

  日期：1986.2

  R-R′, RBr and R′Br. The formation of the products R-R′ is increasingly favoured the greater the electronegativity of the organic ligands. The reductive elimination giving RBr takes place more readily the greater the electronegativity of the organic ligand R. The product of the reductive elimination reaction is “NiIBr”, “NiIR”, or “NiIR′”, which in the presence of bromine give Ni2+, [NiBr(RBr)L2], phosphonium

  已经对化合物t- [NiRR'L 2 ]（L = PMe 2 Ph和PEt 3； R =芳基或乙烯基）和[Ni（mes）（邻甲苯基）bipy]的分解进行了研究（ mes = mesityl）通过电化学方法或溴氧化诱导。镍的无有机金属化合物III，分离在上述反应中，但Ni的五配位中间体III推测。Ni III中间体形成后很容易发生分解。如果分解是电化学诱导的，则中间体分解，仅给出偶联产物RR'。当溴用作氧化剂时，Ni III仅在配体的体积允许与中心原子配位的情况下形成中间体。因此，[Ni（C 2 Cl 3）（mes）（PMe 2 Ph）2完全不分解，仅获得[Ni（C 2 Cl 3）（mesBr 2）（PMe 2 Ph）2 ]。中间体“ Ni III RR'BrL 2进行还原性消除，得到RR'，RBr和R'Br。有机配体的电负性越大，越来越倾向于形成产物RR'。有机配体R的电负性越大，给出RB
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: C: MVol.D2, 4.3.5.5, page 381 - 382
  作者：

  DOI：——

  日期：——
• Steudel, R., Zeitschrift fur Naturforschung, 1968, vol. 23 b, p. 1163 - 1171
  作者：Steudel, R.

  DOI：——

  日期：——
• Squaric acid difluoride
  作者：Michael Senzlober、Hans Bürger、Reint Eujen、Achim Gelessus、Walter Thiel

  DOI：10.1016/s0022-1139(99)00138-4

  日期：1999.11

  Hitherto unknown squaric acid difluoride (3,4-difluoro-3-cyclobutene-1,2-dione) (1a) has been synthesized in 71% yield by gas phase fluorination of squaric acid dichloride (1c) with KF at 250 degrees C. (1a) has been characterized by multinuclear NMR, mass, IR and Raman spectra. The IR spectrum is in excellent agreement with its ab initio prediction (MP2, 6-311 + G(2d, p)). The vacuum thermolysis of (1a) at 700 degrees C does not yield the expected decarbonylation product FCCF (2a) although the precursor of the latter, F2CCCO, and three C3F4 isomers (propyne, allene, cyclopropene) which are also found as decomposition products of (2a) have been identified. (C) 1999 Elsevier Science S.A. All rights reserved.
• Chemical routes to fine tuning the redox potential of monolayers covalently attached on H–Si(100)
  作者：Andrea Giacomo Marrani、Fabrizio Cattaruzza、Franco Decker、Pierluca Galloni、Robertino Zanoni

  DOI：10.1016/j.electacta.2010.05.009

  日期：2010.8

  A closely related series of three ferrocene derivatives, bearing a short carbon-carbon tethering arm for covalent attachment to H-terminated Si(1 0 0). has been used to produce electroactive hybrid materials. Three different grafting procedures have been applied for the first time on this type of molecules in order to obtain the full series of possible unsaturations in the C-C lateral chain bound to Si: ethyl, vinyl and ethynyl group, respectively, associated with the surface species (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-CH2-CH2-Si (EtFC/Si), (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-CH=CH-Si (VFC/Si), and (eta(5)-C5H5)Fe2+(eta(5)-C5H4)-C C-Si (EFC/Si).The surface reactions here applied involve Grignard derivatization, Lewis acid catalysis and nucleophilic substitution by an acetylide anion. The redox potentials of the three molecule/surface hybrids, measured by cyclic voltammetry, are 0.059, 0.136 and 0.251 V vs. Ag/Ag+, respectively, from EtFC/Si to EFC/Si and are supposedly following the increasing trend of the extent of unsaturation in the tethering arm. The above trend in redox potentials parallels the one experimentally found and theoretically reproduced for the corresponding isolated molecules, which shows that the adopted functionalization procedures may be used to control the number of residual unsaturations in the C-C arm. The presence and chemical nature of the redox species covalently attached to Si are strongly supported after evaluation of XPS spectra and electrochemical data. The formation of electroactive hybrids on Si with tuneable well-defined switching potentials can be highly beneficial to the development of Si-based memory devices. (C) 2010 Elsevier Ltd. All rights reserved.