silver cyanide | 330660-35-0

• 分子结构分类: 无机化合物 - 混合金属/非金属化合物 - 过渡金属有机体
• 英文名称: silver cyanide
• 英文别名: silver(I) cyanide；[Ag(CN)]；silver;cyanide
• CAS: 330660-35-0
• 化学式: Ag*CN
• 分子量: 133.886
• InChiKey: LFAGQMCIGQNPJG-UHFFFAOYSA-N

物化性质

• 物理描述：
  Silver cyanide appears as a white to gray odorless tasteless powder that darkens on exposure to light. Insoluble in water. Toxic by skin absorption through open wounds, ingestion and inhalation of dust. Toxic oxides of nitrogen are produced in fires.
• 颜色/状态：
  White or grayish powder
• 气味：
  Odorless
• 味道：
  Tasteless
• 熔点：
  320 °C (decomposes)
• 溶解度：
  0.000023 G/100 CC WATER AT 20 °C
• 密度：
  3.95 at 19 °C (referred to water at 4 °C)
• 稳定性/保质期：
  STABLE IN DRY AIR
• 分解：
  Toxic gases and vapors (such as hydrogen cyanide and carbon monoxide) may be released when cyanide decomposes. /Cyanide/
• 腐蚀性：
  Corrosive to aluminum.
• 折光率：
  Index of refraction: 1.685
• 解离常数：
  Ksp= 1.6x10-14 at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 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：
  23.8
• 氢给体数：
  0
• 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酸盐。氰化物代谢物通过尿液排出。银化合物也可以通过口服和皮肤吸收。它在血液中分布到全身，尤其是肝脏。不溶性的银盐转化为可溶性的银硫化蛋白酸盐，与RNA、DNA和蛋白质中的氨基或羧基团结合，或者被抗坏血酸或多巴胺还原成金属银。金属银被氧化后可能会沉积在组织中，导致皮肤发蓝（阿蕊吉亚）。银主要通过粪便排出体外。（L808, L96）

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. Silver compounds can also be absorbed orally and dermally. It distributes throughout the body in the blood, particularily to the liver. Insoluble silver salts are transformed into soluble silver sulfide albuminates, bind to amino or carboxyl groups in RNA, DNA, and proteins, or are reduced to metallic silver by ascorbic acid or catecholamines. Metallic silver is oxidized and may deposit in the tissues, causing arygria. Silver is eliminated primarily in the faeces. (L808, 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的细胞色素c氧化酶的抑制剂（存在于真核细胞线粒体的膜中）。它与这种酶中的三价铁原子形成复合物。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用于能量的ATP。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物还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三价铁离子结合形成无活性的氰化变性血红蛋白。金属银被氧化并可能在组织中沉积，导致银质沉着病。银离子已知能抑制谷胱甘肽过氧化物酶和Na+,K+-ATP酶活性，分别破坏硒催化的巯基氧化还原反应和细胞内离子浓度。银纳米颗粒被认为会破坏线粒体呼吸链，导致氧化应激、ATP合成减少和DNA损伤。（L808, A243, A244, A245, A246, 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. Metallic silver is oxidized and may deposit in the tissues, causing arygria. The silver ion is known to inhibit glutathione peroxidase and NA+,K+-ATPase activity, disrupting selenium-catalyzed sulfhydryl oxidation-reduction reactions and intracellular ion concentrations, respectively. Silver nanoparticles are believed to disrupt the mitochondrial respiratory chain, causing oxidative stress, reduced ATP synthesis, and DNA damage. (L808, A243, A244, A245, A246, L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

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损害大脑和心脏，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、血变化、头痛和甲状腺肿大。皮肤接触氰化物盐可能会引起刺激和产生溃疡。长期接触高浓度的银可能会导致一种称为银质沉着症的状况，即皮肤和其他身体组织出现蓝灰色色素沉着。银质沉着症是一种永久性效应，但似乎对健康没有危害。虽然银本身不具毒性，但大多数银盐都有毒，可能会损害肝脏、肾脏和中央神经系统，并且可能具有致癌性。

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. Exposure to high levels of silver for a long period of time may result in a condition called arygria, a blue-gray discoloration of the skin and other body tissues. Argyria is a permanent effect but does not appear to be harmful to health. While silver itself is not toxic, most silver salts are, and may damage the liver, kidney, and central nervous system, as well as be carcinogenic. (L808, L809, L810, L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L96）；口服（L96）；皮肤（L96）

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

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

氰化物中毒表现为呼吸急促、气短、全身无力、眩晕、头痛、晕厥、混乱、抽搐/癫痫发作，最终可能失去意识。长期接触高浓度的银可能导致一种称为银质症（argyria）的状况，这是一种皮肤和其他身体组织呈现蓝灰色的色素沉着。银质症是永久性的，但似乎对健康无害。空气中高浓度的银可能导致呼吸问题、肺和喉咙刺激以及胃痛。银与皮肤的接触可能在某些人中引起轻微的过敏反应，如皮疹、肿胀和炎症。

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. Exposure to high levels of silver for a long period of time may result in a condition called arygria, a blue-gray discoloration of the skin and other body tissues. Argyria is a permanent effect but does not appear to be harmful to health. Exposure to high levels of silver in the air has resulted in breathing problems, lung and throat irritation, and stomach pains. Skin contact with silver can cause mild allergic reactions such as rash, swelling, and inflammation in some people. (L808, L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  silver cyanide 以 neat (no solvent) 为溶剂， 以75%的产率得到氰
  参考文献：
  名称：

  低温下 Pd(110) 上的氰吸附：角分辨光电发射、Leed 和热解吸的研究

  摘要：

  摘要 使用热解吸光谱 (TDS)、角分辨紫外光电子能谱 (ARUPS)、LEED 和功函数测量，研究了氰、C 2 N 2 在 Pd(110) 上的吸附与温度的关系。在低于 100 K 的温度下形成多层；将这些闪蒸到逐渐升高的温度会产生几种不同的表面状态。在 200 K 下，获得了显示 ac(2 × 2) LEED 图案并指定为平行键合 C 2 N 2 分子的单层的状态。分子主要垂直于Pd原子的密集排，即沿[001]排列。观察和分配了六个价轨道电离；这些分配表明与表面的强 π 相互作用。高于 200 K 会发生解离为 CN。100 到 200 K 之间的解吸很复杂；有一些证据表明这里存在倾斜的分子种类。

  DOI：

  10.1016/0039-6028(89)90540-2
• 作为产物：
  描述：

  silver cyanate 在 calcium 作用下， 以 氨 为溶剂， 生成 silver cyanide
  参考文献：
  名称：

  A Study of the Products Obtained by the Reducing Action of Metals upon Salts in Liquid Ammonia Solution. V. The Action of Calcium upon Silver Salts

  摘要：

  DOI：

  10.1021/ja01282a009
• 作为试剂：
  描述：

  FMOC-N-甲基-L-丙氨酸 在 四(三苯基膦)钯 、 silver cyanide 、 草酰氯 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Total Synthesis of NW-G01, a Cyclic Hexapeptide Antibiotic, and 34-epi-NW-G01

  摘要：

  NW-G01, a cyclic hezapeptide antibiotic, and 34-epi-NW-G01 were synthesized by the highly stereoselective convergent approach for the first time, thereby unambiguously determining the absolute structure of NW-G01.

  DOI：

  10.1021/ol201912w

文献信息

• Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions
  作者：Yunwei Chen、Xiang Sun、Ningjie Wu、Jingbai Li、Shengnan Jin、Yongliang Zhong、Zirui Liu、Andrey Rogachev、Hyun-Soon Chong

  DOI：10.1039/c5ob01692d

  日期：——

  Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three-membered ring cogeners, aziridines and epoxides. The characterization of both optically active aziridinium ions and secondary β-halo amines as the

  iri啶鎓离子是用于合成对映体富集的结构单元的有用的反应性中间体。然而，与其他三元环同源热氮，氮丙啶和环氧化物相比，N，N-二烷基叠氮鎓离子在光学活性分子的合成中相对未被充分利用。几乎没有报道光学活性的叠氮鎓离子和仲β-卤代胺作为叠氮鎓离子的前体分子的表征，并且常常不清楚。在本文中，我们首次报道了旋光性叠氮鎓离子和仲β-卤代胺的制备以及实验和理论表征。旋光性次生N，NN，N-取代的丙氨醇通过卤化物在氮丙啶鎓离子的更受阻的碳上形成和开环而有效地合成了N-取代的β-卤代胺。通过NMR和计算分析对旋光性β-卤代胺和叠氮鎓离子进行了表征。通过X射线晶体学分析确认旋光性β-氯胺的结构。来自N，N的叠氮鎓离子-二苄基丙二醇仅在数小时内保持稳定，这对于分析NMR和光学活性而言足够长。使用DFT和高精度DLPNO-CCSD（T）方法，通过计算研究了卤化物对氮丙啶鎓离子的立体定向开环。氮丙啶鎓离子的高度区域
• Fourier-transform electronic absorption spectroscopy: The 800 nm near-infrared band system of nitrosyl cyanide (NCNO)
  作者：Josef Pfab

  DOI：10.1016/0009-2614(83)80175-4

  日期：1983.8

  Dispersed and Fourier-transform spectra of NCNO vapour have been measured and some of the vibrational and coarse rotational structure has been analysed. The absorption is due to a 1A″ ← 1A′(n_,π*) transition with the origin at 882.2 nm. The main geometry change accompanying the transition consists of an opening up of the CNO angle.

  测量了NCNO蒸气的分散光谱和傅立叶变换光谱，并分析了一些振动和粗糙的旋转结构。的吸收是由于1名A“← 1个A'（N_，π*），在882.2处的原点过渡。伴随过渡的主要几何形状变化包括CNO角的张开。
• Synthesis, <i>in silico</i> and <i>in vitro</i> Evaluation of Novel Oxazolopyrimidines as Promising Anticancer Agents
  作者：Yevheniia Velihina、Thomas Scattolin、Denys Bondar、Stepan Pil'o、Nataliya Obernikhina、Olesksiy Kachkovskyi、Ivan Semenyuta、Isabella Caligiuri、Flavio Rizzolio、Volodymyr Brovarets、Yevgen Karpichev、Steven P. Nolan

  DOI：10.1002/hlca.202000169

  日期：2020.12

  been synthesized using two main approaches: the pyrimidine ring annulation on a functionalized oxazole and the benzoyl bromide trimerization followed by rearrangement and formation of the oxazolo[5,4‐d]pyrimidine scaffold. The docking analyzes have shown that 7‐piperazine substituted oxazolo[4,5‐d]pyrimidines 8a–8c could be potential VEGFR2 inhibitors with high free energy of ligand–protein complex

  使用两种主要方法合成了新的潜在生物活性恶唑并嘧啶：在功能化的恶唑上环嘧啶环和苯甲酰溴三聚，然后重排和形成恶唑并[5,4- d ]嘧啶骨架。对接分析表明，7-哌嗪取代的恶唑并[4,5- d ]嘧啶8a - 8c可能是潜在的VEGFR2抑制剂，具有高自由能的配体-蛋白质复合物形成（ΔG：-10.1，-9.6，-9.8 kcal / mol）。体外抗肿瘤试验证实了恶唑并[4,5- d ]嘧啶8a - 8c的理论预测含有带正电荷的哌嗪部分的化合物应显示出明显更高的细胞毒性作用。4- [5-（4-氯苯基）-2-苯基[1,3]恶唑[4,5 - d ]嘧啶-7-基]哌嗪-1-三氟乙酸铵（8c）表现出较高的抗增殖作用（IC 50 = 0.21μ米）比多柔比星（IC 50 = 0.36μ米对MDA-MB-231细胞系），并且对OVCAR-3（比较好的效果IC 50 = 1.7μ米）和HCT-116（IC 50
• Structural Variations and Spectroscopic Properties of Luminescent Mono- and Multinuclear Silver(I) and Copper(I) Complexes Bearing Phosphine and Cyanide Ligands
  作者：Yong-Yue Lin、Siu-Wai Lai、Chi-Ming Che、Fu、Zhong-Yuan Zhou、Nianyong Zhu

  DOI：10.1021/ic048876k

  日期：2005.3.1

  Reaction of equimolar amounts of AgCN and PCy3 gave the polymer [(Cy3P)Ag(NCAgCN)]infinity (1), whereas employment of excess PCy3 yielded the discrete compound [(Cy3P)2Ag(NCAgCN)] (2). Reacting bis(dicyclohexylphosphino)methane (dcpm) with AgCN in 1:1 and 1:2 molar ratios gave two crystalline forms, namely [Ag2(mu-dcpm)2][Ag(CN)2]2 x (CH3OH)2 (3a x (CH3OH)2) and [Ag2(mu-dcpm)2][Ag(CN)2]2 (3b), respectively

  等摩尔量的AgCN和PCy3反应得到聚合物[（Cy3P）Ag（NCAgCN）]无穷大（1），而过量PCy3的使用则产生了离散化合物[（Cy3P）2Ag（NCAgCN）]（2）。双（二环己基膦基）甲烷（dcpm）与AgCN以1：1和1：2摩尔比反应产生两种结晶形式，即[Ag2（mu-dcpm）2] [Ag（CN）2] 2 x（CH3OH）2（ 3a x（CH3OH）2）和[Ag2（mu-dcpm）2] [Ag（CN）2] 2（3b）分别表示。CuCN与PCy3的类似反应得到聚合化合物[（（Cy3P）Cu（CN）} 3]无穷大（4），而dcpm处理CuCN则得到[Cu2（mu-dcpm）2（CN）2]（5 ）。使用具有更长的-（CH2）n-间隔基的二膦配体，例如1,2-双（二环己基膦基）乙烷（dcpe，n = 2）和1,3-双（二苯基膦基）丙烷（dppp，n = 3），与[Cu（CH3CN）4]
• Lipshutz-type bis(amido)argentates for directed <i>ortho</i> argentation
  作者：Noriyuki Tezuka、Keiichi Hirano、Andrew J. Peel、Andrew E. H. Wheatley、Kazunori Miyamoto、Masanobu Uchiyama

  DOI：10.1039/c9sc06060j

  日期：——

  aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics-

  双（酰胺基）银盐（TMP）2 Ag（CN）Li 2（3，TMP-Ag-酸盐; TMP = 2,2,6,6-四甲基哌啶子基）被设计为通过空前的定向原位化学键进行化学选择性芳族官能化的工具（D o Ag）。X射线晶体学分析表明3具有与相应的Lipshutz铜酸盐类似的结构。d Ø具有这种TMP-Ag-酸酯的Ag在具有高化学选择性和与各种官能团相容性的工艺中，以高收率提供了多官能芳烃。这些包括对有机金属和过渡金属敏感的取代基，例如甲酯，醛，乙烯基，碘，（三氟甲磺酰基）氧基和硝基。白蚁类药物与各种亲电试剂显示出良好的反应性。硫属元素（S，Se和Te）的安装和偶氮偶合反应也有效进行。