异氰酸酯 | 75-13-8

• 物质功能分类: 化学试剂 - 有机试剂 - 氰酸酯/异氰酸酯
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 异氰酸酯
• 中文别名: 異氰酸；异氰酸
• 英文名称: isocyanic acid
• 英文别名: cyanic acid
• CAS: 75-13-8
• 化学式: CHNO
• 分子量: 43.025
• InChiKey: OWIKHYCFFJSOEH-UHFFFAOYSA-N

物化性质

• 熔点：
  -86 °C
• 沸点：
  41.91°C (rough estimate)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  3
• 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：
  40.9
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

氰化物可以通过口服、吸入和皮肤途径迅速被吸收，并分布到全身。氰化物主要通过罗丹酶或3-巯基丙酸硫转移酶代谢成硫氰化物。氰化物的代谢物通过尿液排出。

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

氰化物是电子传递链第四个复合体中细胞色素c氧化酶的抑制剂（存在于真核细胞线粒体膜中）。它与这种酶中的铁原子形成复合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。因此，电子传递链被中断，细胞无法再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到的影响尤为严重。氰化物也通过结合过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶和Cu/Zn超氧化物歧化酶来产生一些毒性效应。氰化物与变性血红蛋白中的铁离子结合，形成无活性的氰化变性血红蛋白。（L97）

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

短时间内接触高浓度的氰化物会对大脑和心脏造成伤害，甚至可能导致昏迷、癫痫、呼吸暂停、心脏骤停和死亡。长期吸入氰化物会引起呼吸困难、胸痛、呕吐、血象改变、头痛和甲状腺肿大。皮肤接触氰化物盐可能会引起刺激并产生溃疡。

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入 (L96)；口服 (L96)；经皮 (L96)

Inhalation (L96) ; oral (L96) ; dermal (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

氰化物中毒的特征包括快速、深大的呼吸和呼吸急促，全身无力，眩晕，头痛，头晕，混乱，抽搐/癫痫发作，最终失去意识。

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2933699090

制备方法与用途

根据上述内容，异氰酸酯主要用于以下行业：

1. 家电：冰箱、空调等设备的保温隔热材料。

2. 汽车：塑料和橡胶部件、座椅泡沫、仪表板等内饰件。

3. 建筑：墙体保温材料、防水涂料、密封胶、粘合剂。

4. 鞋业：鞋底发泡材料、内衬、鞋面涂层。

5. 家具：海绵、软垫、泡沫填充物。

6. 胶粘剂：热塑性聚氨酯弹性体、热固性树脂等合成胶黏剂的原料。

反应信息

• 作为反应物：
  描述：

  异氰酸酯 在 H₃N*Ti 作用下， 生成 氰胺
  参考文献：
  名称：

  A Facile Synthesis of Pd–C3N4@Titanate Nanotube Catalyst: Highly Efficient in Mizoroki–Heck, Suzuki–Miyaura C–C Couplings

  摘要：

  A Pd-C3N4@titanate nanotube (Pd-C3N4@TNT) catalyst workable in water medium, robust against leaching and agglomeration was prepared in a facile synthetic procedure using quite common chemicals such as TiO2 powder, urea and palladium acetate. The Pd-C3N4@TNT catalyst has been characterized by BET surface area and pore size distribution, X-ray diffraction, solid-state C-13 NMR spectroscopy, X-ray photoelectron spectroscopy and transmission electron microscopy. The Pd-C3N4@TNT is a green catalyst for the Miziroki-Heck and Suzuki-Miyaura C-C coupling reactions in water medium with high efficiency (> 99% product yields) due to atomic level immobilization of Pd in C3N4 networked titanate nanotubes. Pd-C3N4@TNT is robust against leaching and agglomeration due to stable and furthermore it is recyclable and usable at least for five repeated cycles. The use of water as solvent, absence of leaching and agglomeration, recyclability and reusability ascertains the greenness of Pd-C3N4@TNT) catalyst and process.Graphic AbstractNovel Pd-C3N4@titanate nanotube catalyst prepared from bulk TiO2 and urea by simple hydrothermal and thermal pyrolysis followed by immobilization of Pd is active and selective for Mizoroki-Heck, Suzuki-Miyaura C-C couplings in water medium.[GRAPHICS].

  DOI：

  10.1007/s10562-019-02955-9
• 作为产物：
  描述：

  silver cyanate 在 硫化氢 作用下， 生成 异氰酸酯
  参考文献：
  名称：

  Birckenbach, L.; Kolb, H., Berichte der Deutschen Chemischen Gesellschaft, 1935, vol. 68, p. 895 - 912

  摘要：

  DOI：

文献信息

• Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity
  作者：Amin Ismael、Carlos Serpa、M. Lurdes S. Cristiano

  DOI：10.1039/c2pp25210d

  日期：2013.2

  -5-ones derived from acyclic and unhindered allylic alcohols previously investigated but photolysis of the tetrazolone derived from the bulkier 3–methylcyclohex-2-enol 4c leads to formation of a benzimidazolone, indicating that, in this case, cyclization of the biradical formed upon extrusion of N2 involves the phenyl substituent and not the allylic moiety. Theoretical calculations (DFT(B3LYP)/3-21G*)

  碳环烯丙基醇衍生的四唑酮的光化学 环己-2-烯醇 和 3-甲基环己-2-烯醇并从天然萜烯醇中提取了神经醇，目的是评估溶剂的影响以及笨重的烯丙基部分对光产品选择性和稳定性的影响。衍生自四唑酮的光解内罗尔 和 环己-2-烯醇通过一种途径提供了相应的嘧啶酮作为主要产物，该途径似乎与先前从无环和无阻碍的烯丙醇衍生而来的其他1-allyl-4-phenyl-1,4-dihydro-5 H -tetrazol-5-one所提议的途径相似进行了研究，但对大体积3-甲基环己-2-烯醇4c衍生的四唑酮进行光解会导致苯并咪唑酮的形成，这表明在这种情况下，N 2挤出时形成的双自由基的环化反应涉及苯基取代基而不是烯丙基部分。进行了理论计算（DFT（B3LYP）/ 3-21G *）以支持对实验结果和机理建议的解释。进行激光闪光光解实验的目的是弄清参与初级光裂解过程的中间体的性质。
• Experimental and Theoretical Understanding of the Gas Phase Oxidation of Atmospheric Amides with OH Radicals: Kinetics, Products, and Mechanisms
  作者：Nadine Borduas、Gabriel da Silva、Jennifer G. Murphy、Jonathan P. D. Abbatt

  DOI：10.1021/jp503759f

  日期：2015.5.14

  reactions proceed via C–H abstraction from alkyl groups and from formyl C(O)–H bonds when available. The latter process leads to radicals that can readily react with O2 to form isocyanates, explaining the detection of toxic compounds such as isocyanic acid (HNCO) and methyl isocyanate (CH3NCO). These contaminants of significant interest are primary oxidation products in the photochemical oxidation of formamide

  大气酰胺具有主要和次要来源，并以较低的pPTv水平存在于环境空气中。与OH基团五个不同的酰胺以更好地评估在大气酰胺的命运，在室温（298±3 K）速率系数在1个确定3烟雾箱使用在线质子转移反应质谱（PTR-小姐）。作为最简单的酰胺，甲酰胺对OH的速率系数为（4.44±0.46）×10 –12 cm 3摩尔–1 s –1，相当于大约1天的大气寿命。N-甲基甲酰胺，N-甲基乙酰胺和丙酰胺（甲酰胺的烷基版本）的速率系数为（10.1±0.6）×10 –12，（5.42±0.19）×10 –12和（1.78±0.43）×10 –12 cm 3摩尔–1 s –1。还研究了乙酰胺，但由于其缓慢的氧化动力学，我们报道的范围为（0.4–1.1）×10 –12 cm 3摩尔–1 s –1其与OH自由基的速率系数。监测并定量氧化产物，并使用简单的动力学盒模型拟合其时间迹线。为了进一步探讨该机理，使用从头算来确定
• Iminopropadienones, RNCCCO: syntheses and reactions
  作者：Thomas Mosandl、C. Oliver Kappe、Robert Flammang、Curt Wentrup

  DOI：10.1039/c39920001571

  日期：——

  Phenyliminopropadienone, PhNCCCO, is prepared and characterized, and initial chemical reactions are described.

  苯亚氨丙二烯酮，PhNCCCO，被制备并表征，同时描述了初步的化学反应。
• 3-Amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: A new class of CDK2 inhibitors
  作者：Paolo Pevarello、Daniele Fancelli、Anna Vulpetti、Raffaella Amici、Manuela Villa、Valeria Pittalà、Paola Vianello、Alexander Cameron、Marina Ciomei、Ciro Mercurio、James R. Bischoff、Fulvia Roletto、Mario Varasi、Maria Gabriella Brasca

  DOI：10.1016/j.bmcl.2005.10.071

  日期：2006.2

  We have recently reported about a new class of Aurora-A inhibitors based on a bicyclic tetrahydropyrrolo[3,4-c]pyrazole scaffold. Here we describe the synthesis and early expansion of CDK2/cyclin A-E inhibitors belonging to the same chemical class. Synthesis of the compounds was accomplished using a solution-phase protocol amenable to rapid parallel expansion. Compounds with nanomolar activity in the

  我们最近报道了一种基于双环四氢吡咯并[3,4-c]吡唑支架的新型Aurora-A抑制剂。在这里，我们描述了属于同一化学类别的CDK2 / cyclin AE抑制剂的合成和早期扩展。使用适合于快速平行扩展的溶液相方案完成化合物的合成。已经获得了在生化分析中具有纳摩尔活性并且能够有效抑制CDK2介导的肿瘤细胞增殖的化合物。
• Analysis of transition state mimicry by tight binding aminothiazoline inhibitors provides insight into catalysis by human O-GlcNAcase
  作者：N. Cekic、J. E. Heinonen、K. A. Stubbs、C. Roth、Y. He、A. J. Bennet、E. J. McEachern、G. J. Davies、D. J. Vocadlo

  DOI：10.1039/c6sc00370b

  日期：——

  2′-Aminothiazoline inhibitors of human OGA are tight binding transition state mimics for which binding depends on inhibitor pK_a.

  2'-氨基噻唑啉抑制剂是人OGA的紧密结合过渡态模拟物，其结合依赖于抑制剂的pKa。