3-cyanopropyldimethylfluorosilane | 1639345-42-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-cyanopropyldimethylfluorosilane
• 英文别名: 4-(fluorodimethylsilyl)butanenitrile；4-(Fluorodimethylsilyl)butanenitrile；4-[fluoro(dimethyl)silyl]butanenitrile
• CAS: 1639345-42-8
• 化学式: C₆H₁₂FNSi
• 分子量: 145.252
• InChiKey: RZHGQUVEZKATLV-UHFFFAOYSA-N

物化性质

• 沸点：
  185.5±23.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)
• LogP：
  2.17 at 20℃ and pH7

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyanopropyldimethylfluorosilane 在 六氟磷酸锂 、 水 作用下， 以 neat (no solvent) 为溶剂， 反应 528.0h， 生成
  参考文献：
  名称：

  增强锂离子电池热稳定性的有机硅电解质的热分解和水解机理

  摘要：

  The high flammability and thermal instability of conventional carbonate electrolytes limit the safety and performance of lithium-ion batteries (LIBs) and other electrochemical energy storage devices. Organosilicon solvents have shown promise due to their reduced flammability and greater chemical stability at high temperatures. A series of organosilicon electrolytes with different functional substituents were studied to understand the structural origins of this enhanced stability. The thermal and hydrolytic stability of organosilicon and carbonate solvents with LiPF6 was probed by storage at high temperatures and with added water. Quantitative monitoring of organosilicon and carbonate electrolyte decomposition products over time using NMR spectroscopy revealed mechanisms of degradation and led to the discovery of a key PF5-complex that forms in organosilicon electrolytes to inhibit further salt breakdown. Increased knowledge of specific structural contributions to electrolyte stability informs the development of future electrolyte solvents to enable the safer operation of high-performing lithium-ion batteries. (C) 2017 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0671709jes
• 作为产物：
  描述：

  (3-氰基丙基)二甲基氯硅烷 在 氟化铵 作用下， 反应 2.5h， 生成 3-cyanopropyldimethylfluorosilane
  参考文献：
  名称：

  锂电池助剂3-氰丙基二甲基氟硅烷的合成方 法

  摘要：

  本发明涉及有机硅化合物合成技术领域，具体涉及一种锂电池助剂3‑氰丙基二甲基氟硅烷的合成方法。所述合成方法为：将4‑氯正丁腈滴加到钠的无水溶剂中进行反应，得到N≡CCH2CH2CH2Na的悬浊液，再经过以下两种路线的任一种，得到3‑氰丙基二甲基氟硅烷；路线一为N≡CCH2CH2CH2Na先和二甲基二氯硅烷反应得到3‑氰丙基二甲基氯硅烷，再经氟化得到3‑氰丙基二甲基氟硅烷；路线二为二甲基二氯硅烷先进行氟化得到二甲基二氟硅烷，再与N≡CCH2CH2CH2Na反应得到3‑氰丙基二甲基氟硅烷。本发明所用原料容易获取、成本低廉、纯度更高，所用方法易于反应，经济可行。

  公开号：

  CN109897059B

文献信息

• [EN] PREPARATION OF FLUOROSILICON COMPOUNDS<br/>[FR] PRÉPARATION DE COMPOSÉS DE FLUOROSILICIUM
  申请人：ARKEMA INC

  公开号：WO2016032767A1

  公开（公告）日：2016-03-03

  Methods of synthesizing fluorosilanes containing cyano-substituted alkyl groups are provided. For example, 3-cyanopropyldimethylfluorosilane may be produced by reacting tetramethyldisiloxane and boron trifluoride to obtain fluorodimethylsilane and then reacting the fluorodimethylsilane with allyl cyanide, in the presence of a hydrosilylation catalyst

  提供了含有氰基取代烷基基团的氟硅烷合成方法。例如，可以通过将四甲基二硅氧烷和三氟化硼反应以获得氟二甲基硅烷，然后在氢硅烷化催化剂存在下将氟二甲基硅烷与丙烯腈反应来制备3-氰丙基二甲基氟硅烷。
• [EN] FUNCTIONALIZED SILANES AND ELECTROLYTE COMPOSITIONS AND ELECTROCHEMICAL DEVICES CONTAINING THEM<br/>[FR] SILANES FONCTIONNALISÉS ET COMPOSITIONS D'ÉLECTROLYTES ET DISPOSITIFS ÉLECTROCHIMIQUES LES CONTENANT
  申请人：SILATRONIX INC

  公开号：WO2016054621A1

  公开（公告）日：2016-04-07

  Described are compounds of the structure R4-a-Si-(Sp-Y)a-Zb, wherein "a" is integer from 1 to 4; "b" is an integer from 0 to (3 x a); "Z," which is absent when "b "R" or formula (II), wherein each "R" is halogen, C1-6 linear or branched alkyl, alkenyl, or alkynyl or C1-6 linear or branched halo-alkyl, halo-alkenyl, or halo-alkynyl; each "Sp" C1-15 linear or branched alkylenyl or CMS linear or branched halo-alkylenyl; and each "Y" an organic polar group. Also described are electrolyte compositions containing one or more of these compounds.

  描述了具有结构R4-a-Si-(Sp-Y)a-Zb的化合物，其中"a"是从1到4的整数；"b"是从0到(3 x a)的整数；"Z"在"b"小于等于(3 x a)时存在，"R"或者公式(II)中不存在，其中每个"R"是卤素，C1-6直链或支链烷基，烯基，或炔基或C1-6直链或支链卤代烷基，卤代烯基，或卤代炔基；每个"Sp"是C1-15直链或支链烷基亚基或CMS直链或支链卤代烷基亚基；每个"Y"是有机极性基团。还描述了含有这些化合物中的一个或多个的电解质组合物。
• METHOD FOR PRODUCING CYANOALKYL FLUOROSILANES
  申请人：Wacker Chemie AG

  公开号：US20180258108A1

  公开（公告）日：2018-09-13

  Cyanoalkylfluorosilanes are prepared in exceptionally high yield by the reaction of the corresponding cyanoalkylchlorosilanes with specific metal fluorides. The products are useful in lithium ion battery electrolyte composition.

  通过将相应的氰基烷基氯硅烷与特定的金属氟化物反应，制备出极高产率的氰基烷基氟硅烷。该产品在锂离子电池电解质组成中非常有用。
• [EN] ALKALI METAL PF 6 SALT STABILIZATION IN CARBONATE SOLUTIONS<br/>[FR] STABILISATION DE SEL DE PF6 DE MÉTAL ALCALIN DANS DES SOLUTIONS DE CARBONATE
  申请人：[en]SILATRONIX, INC.

  公开号：WO2023220034A1

  公开（公告）日：2023-11-16

  Disclosed herein is a stabilized salt-in-solvent mixture comprising a salt, a carbonate solvent, and an organosilicon (OS) compound, wherein the OS compound suppresses degradation reactions within the salt-in-solvent mixture. Also disclosed herein is a method of mitigating degradation of a salt/carbonate solution comprising adding to the salt/carbonate solution an amount of an OS compound that suppresses degradation reactions within the salt/carbonate solution. This OS compound may be added to the carbonate solvent before or after dissolution of the salt to form the salt-in-solvent mixture.
• Thermal and Hydrolytic Decomposition Mechanisms of Organosilicon Electrolytes with Enhanced Thermal Stability for Lithium-Ion Batteries
  作者：Sarah L. Guillot、Adrian Peña-Hueso、Monica L. Usrey、Robert J. Hamers

  DOI：10.1149/2.0671709jes

  日期：——

  The high flammability and thermal instability of conventional carbonate electrolytes limit the safety and performance of lithium-ion batteries (LIBs) and other electrochemical energy storage devices. Organosilicon solvents have shown promise due to their reduced flammability and greater chemical stability at high temperatures. A series of organosilicon electrolytes with different functional substituents were studied to understand the structural origins of this enhanced stability. The thermal and hydrolytic stability of organosilicon and carbonate solvents with LiPF6 was probed by storage at high temperatures and with added water. Quantitative monitoring of organosilicon and carbonate electrolyte decomposition products over time using NMR spectroscopy revealed mechanisms of degradation and led to the discovery of a key PF5-complex that forms in organosilicon electrolytes to inhibit further salt breakdown. Increased knowledge of specific structural contributions to electrolyte stability informs the development of future electrolyte solvents to enable the safer operation of high-performing lithium-ion batteries. (C) 2017 The Electrochemical Society. All rights reserved.