2-cyanoethyl 2-cyanoacrylate | 1259537-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyanoethyl 2-cyanoacrylate
• 英文别名: cyanoethylcyanoacrylate；2-Cyanoethyl 2-cyanoprop-2-enoate
• CAS: 1259537-54-6
• 化学式: C₇H₆N₂O₂
• 分子量: 150.137
• InChiKey: YYMHAISUIVEQBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酸酐 、 cyanoethylcyanoacrylate anthracene adduct 在 四磷十氧化物 、 对苯二酚 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 56.0h， 生成 2-cyanoethyl 2-cyanoacrylate 、 dibenzobarallene
  参考文献：
  名称：

  Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development

  摘要：

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.

  DOI：

  10.1021/ma400837h

文献信息

• Synthesis and characterization of four alkyl 2-cyanoacrylate monomers and their precursors for use in latent fingerprint detection
  作者：Mark Tahtouh、John R. Kalman、Brian J. Reedy

  DOI：10.1002/pola.24449

  日期：2011.1.1

  Four novel cyanoacrylates, 2‐cyanoethyl 2‐cyanoacrylate, 1‐cyanoethyl 2‐cyanoacrylate, trideuteromethyl 2‐cyanoacrylate and pentadeuteroethyl 2‐cyanoacrylate have been synthesized using a Diels‐Alder protection/deprotection route involving anthracene. The common route for the synthesis of alkyl 2‐cyanoacrylates was found to be unsatisfactory for the production of small quantities of the targeted cyanoacrylates

  使用涉及蒽的狄尔斯-阿尔德保护/脱保护路线合成了四种新颖的氰基丙烯酸酯，2-氰基乙基2-氰基丙烯酸酯，1-氰基乙基2-氰基丙烯酸酯，3-氘代甲基2-氰基丙烯酸酯和十五烷基-乙基2-氰基丙烯酸酯。人们发现，合成2-氰基丙烯酸烷基酯的通用途径不能令人满意地生产少量的目标氰基丙烯酸酯，这些氰基丙烯酸酯有可能用作在困难表面上进行指纹的中红外光谱成像的试剂。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2010年
• Quick-setting adhesive composition
  申请人：JAPAN SYNTHETIC RUBBER CO., LTD.

  公开号：EP0026665A1

  公开（公告）日：1981-04-08

  A quick-setting adhesive composition comprises a 2-cyanoacrylate and at least one 1,1-disubstituted diene, the amount of said diene being greater than 50% of the total weight of the two components. This composition can be used in place of conventional 2-cyanoacrylate adhesives but has improved impact resistance, peel resistance, heat resistance and water resistance.

  一种速凝粘合剂组合物由 2-氰基丙烯酸酯和至少一种 1,1-二取代二烯组成，所述二烯的含量大于两种成分总重量的 50%。这种组合物可以替代传统的 2-氰基丙烯酸酯粘合剂，但具有更好的抗冲击性、抗剥离性、耐热性和耐水性。
• US4196271A
  申请人：——

  公开号：US4196271A

  公开（公告）日：1980-04-01
• US4313865A
  申请人：——

  公开号：US4313865A

  公开（公告）日：1982-02-02
• Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development
  作者：Alfonso Bentolila、Jalindar Totre、Ilana Zozulia、Michal Levin-Elad、Abraham J. Domb

  DOI：10.1021/ma400837h

  日期：2013.6.25

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.