溴(氟)乙腈 | 96449-14-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 溴(氟)乙腈
• 英文名称: bromofluoroacetonitrile
• 英文别名: bromofluoro acetonitrile；2-bromo-2-fluoroacetonitrile
• CAS: 96449-14-8
• 化学式: C₂HBrFN
• mdl: MFCD07784278
• 分子量: 137.939
• InChiKey: PABLWEPPFMSACN-UHFFFAOYSA-N

物化性质

• 沸点：
  70.9±20.0 °C(Predicted)
• 密度：
  1.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T

反应信息

• 作为反应物：
  描述：

  溴(氟)乙腈 、 1,3-戊二醇 在 硫酸 作用下， 生成 2-(bromofluoromethyl)-4,4,6-trimethyl-1,3-oxazine
  参考文献：
  名称：

  A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide

  摘要：

  We report here the transformation of aldehydes to their (Z)-alpha-fluoro-alpha,beta-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.017
• 作为产物：
  描述：

  溴氟乙酰胺 在 四磷十氧化物 作用下， 生成 溴(氟)乙腈
  参考文献：
  名称：

  A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide

  摘要：

  We report here the transformation of aldehydes to their (Z)-alpha-fluoro-alpha,beta-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.017

文献信息

• Halonitriles, their preparation and use to make halopyridines
  申请人：The Dow Chemical Company

  公开号：US04562009A1

  公开（公告）日：1985-12-31

  Novel halonitriles, e.g., 2,4-dichloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile, method of preparation and use to make halopyridines, some of which are novel, e.g., 2-chloro-3-fluoro-5-methylpyridine. These compounds are intermediates in the preparation of pharmaceutical and agricultural products.

  新型卤代腈化合物，例如2,4-二氯-2-氟-5,5-二甲氧基-4-甲基戊腈，其制备方法及用于制备卤代吡啶，其中一些是新型的，例如2-氯-3-氟-5-甲基吡啶。这些化合物是制备药物和农业产品的中间体。
• 2-Fluoro-2-cyanoethenyl cyclopropane carboxylates as pesticides
  申请人：Roussel Uclaf

  公开号：US04565822A1

  公开（公告）日：1986-01-21

  Novel cyclopropanecarboxylates in all possible isomeric forms or mixtures thereof of the formula ##STR1## with a 1R,cis or 1R,trans structure and wherein X is a halogen, R is selected from the group consisting of (A) optionally unsaturated alkyl of 2 to 12 carbon atoms, (B) optionally unsaturated cycloalkyl of 3 to 12 carbon atoms, (c) ##STR2## Z is selected from the group consisting of --C.tbd.CH, --CH.sub.3 and --CN and Ar is selected from the group consisting of --C.sub.6 H.sub.5, --C.sub.6 F.sub.5, ##STR3## B is hydrogen or fluorine and X is fluorine, chlorine or bromine ##STR4## Y.sub.2 is selected from the group consisting of hydrogen, fluorine, chlorine bromine, --C.tbd.N and --C.tbd.CH, Y.sub.3, Y.sub.4, and Y.sub.5 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms optionally substituted by one or more functional groups, alkenyl of 2 to 8 carbon atoms and alkynyl of 2 to 8 carbon atoms, and two of Y.sub.3, Y.sub.4 and Y.sub.5 can form rings between them with the proviso that if X is bromine and R is ##STR5## and Z is cyano or ethynyl and A.sub.r is ##STR6## the carbon carrying Z is in the (S) configuration and the double bond in the 3-side chain may have E or Z structure useful in combatting pests such as insects, nematodes acarids.

  式子为##STR1##的所有可能异构体或其混合物的新型环丙烷羧酸酯，其中1R，顺式或1R，反式结构，X是卤素，R选择自由基组，包括（A）2-12个碳原子的可选不饱和烷基，（B）3-12个碳原子的可选不饱和环烷基，（C）##STR2##，Z选择自由基组，包括--C.tbd.CH，--CH.sub.3和--CN，Ar选择自由基组，包括--C.sub.6 H.sub.5，--C.sub.6 F.sub.5，##STR3##，B是氢或氟，X是氟、氯或溴##STR4##，Y.sub.2选择自由基组，包括氢、氟、氯、溴、--C.tbd.N和--C.tbd.CH，Y.sub.3，Y.sub.4和Y.sub.5分别选择自由基组，包括氢、氟、氯、溴、1-8个碳原子的烷基和3-8个碳原子的环烷基，可选地被一个或多个功能基取代，2-8个碳原子的烯基和2-8个碳原子的炔基，Y.sub.3，Y.sub.4和Y.sub.5中的两个可以在它们之间形成环，但如果X是溴，R是##STR5##，Z是氰基或乙炔基，A.sub.r是##STR6##，则携带Z的碳处于（S）构型，3侧链中的双键可能具有E或Z结构，可用于对抗害虫如昆虫，线虫和螨虫。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.9, 7, page 50 - 101
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• US3121734
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