二乙基汞 | 627-44-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 烷基金属
• 中文名称: 二乙基汞
• 中文别名: 二乙(基)汞
• 英文名称: diethylmercury
• 英文别名: Diaethyl-quecksilber；Diethylquecksilber；Quecksilberdiaethyl
• CAS: 627-44-1
• 化学式: C₄H₁₀Hg
• 分子量: 258.713
• InChiKey: SPIUPAOJDZNUJH-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  请远离强氧化剂、强酸和卤素。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

有机汞主要通过消化道吸收，然后通过血液分布到全身。有机汞与自由的半胱氨酸以及血红蛋白等蛋白质上的半胱氨酸和巯基团结合。这些复合物能够模拟甲硫氨酸，从而被运输到全身，包括通过血脑屏障和胎盘。有机汞代谢成无机汞，最终通过尿液和粪便排出体外。

Organic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. (T11)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

汞离子与蛋白质的巯基或硫醇基团的高亲和力结合被认为是汞活性的主要机制。通过改变细胞内巯基状态，汞可以促进氧化应激、脂质过氧化、线粒体功能障碍和血红素代谢的变化。已知汞能与微囊和线粒体酶结合，导致细胞损伤和死亡。例如，汞能抑制水通道蛋白，阻止细胞膜上的水流。它还抑制蛋白质LCK，导致T细胞信号传导减少和免疫系统抑制。汞还被认为是通过作用于突触后神经元膜来抑制神经兴奋性。它还通过抑制蛋白激酶C和碱性磷酸酶来影响神经系统，这会损害脑微血管的形成和功能，以及改变血脑屏障。有机汞通过结合微管蛋白，阻止微管组装和导致有丝分裂抑制，从而产生发育效应。汞还能产生自身免疫反应，可能是通过修饰主要组织相容性复合体（MHC）II类分子、自身肽、T细胞受体或细胞表面粘附分子。

High-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. (L7, A8, A25, A26)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

水银主要影响神经系统。接触高水平的金属汞、无机汞或有机汞可能导致大脑、肾脏和发育中的胎儿永久性损害。对大脑功能的影响可能导致易怒、害羞、震颤、视力或听力改变以及记忆问题。儿童的水银中毒，即手足粉红病，特点是手和脚疼痛和粉红色变色。水银中毒还可能引起亨特-拉塞尔综合症和熊本病。

Mercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. (L7)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L7）；吸入（L7）；皮肤给药（L7）

Oral (L7) ; inhalation (L7) ; dermal (L7)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

常见症状包括周围神经病变（表现为感觉异常、瘙痒、灼热或疼痛），皮肤变色（红润的面颊、指尖和脚趾），水肿（肿胀）以及脱屑（死皮层层脱落）。

Common symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). (A5)

来源:Toxin and Toxin Target Database (T3DB)

制备方法与用途

合成制备方法是由乙基溴化镁与氯化汞在乙醚中反应得到的。

反应信息

• 作为反应物：
  描述：

  二乙基汞 在 arsenic trichloride 作用下， 生成 乙基二氯胂
  参考文献：
  名称：

  Steinkopf; Mieg, Chemische Berichte, 1920, vol. 53, p. 1015

  摘要：

  DOI：
• 作为产物：
  描述：

  氯化乙基汞 在 吡啶 、 铜 作用下， 生成 二乙基汞
  参考文献：
  名称：

  Hein; Wagler, Chemische Berichte, 1925, vol. 58, p. 1500,1506

  摘要：

  DOI：
• 作为试剂：
  描述：

  对二甲苯 在 sodium 、 二乙基汞 作用下， 生成 对甲基苯乙酸
  参考文献：
  名称：

  Schorigin, Chemische Berichte, 1910, vol. 43, p. 1942

  摘要：

  DOI：

文献信息

• Protection of Endogenous Thiols against Methylmercury with Benzimidazole-Based Thione by Unusual Ligand-Exchange Reactions
  作者：Mainak Banerjee、Ramesh Karri、Ashish Chalana、Ranajit Das、Rakesh Kumar Rai、Kuber Singh Rawat、Biswarup Pathak、Gouriprasanna Roy

  DOI：10.1002/chem.201605238

  日期：2017.4.27

  (GSH) to form MeHgCys and MeHgSG complexes. Herein, it is reported that the N,N‐disubstituted benzimidazole‐based thione 1 containing a N−CH2CH2OH substituent converts MeHgCys and MeHgSG complexes to less toxic water‐soluble HgS nanoparticles (NPs) and releases the corresponding free thiols CysH and GSH from MeHgCys and MeHgSG, respectively, in solution by unusual ligand‐exchange reactions in phosphate

  甲基汞（MeHg +）等有机物是对人类最具毒性的物质。除了抑制蛋白质外，MeHg +还通过与内源性巯基半胱氨酸（CysH）和谷胱甘肽（GSH）牢固结合形成MeHgCys和MeHgSG复合物，发挥细胞毒性作用。在此，据报道含有N-CH 2 CH 2的N，N-二取代的苯并咪唑基硫酮1OH取代基将MeHgCys和MeHgSG复合物转化为毒性较小的水溶性HgS纳米颗粒（NPs），并通过在37°C下在磷酸盐缓冲液中进行不寻常的配体交换反应，分别从MeHgCys和MeHgSG中释放出相应的游离硫醇CysH和GSH。但是，尽管含有N-CH 2 CH 2 OH取代基，但相应的N-取代的苯并咪唑基硫酮7和N，N-二取代的咪唑基硫酮3未能转化MeHgX（X = Cys和SG）到相同的反应条件下的HgS的NP，这表明不仅N-CH 2 CH 2 OH基团，但在苯并咪唑环和N，N-二取代1导致在1：1 MeHg共轭
• Cleavage of Hg–C Bonds of Organomercurials Induced by Im^OHSe via Two Distinct Pathways
  作者：Mainak Banerjee、Gouriprasanna Roy

  DOI：10.1021/acs.inorgchem.7b01301

  日期：2017.11.6

  the remarkable ability to degrade methylmercury by two distinct pathways. Under basic conditions, ImOHSe converts MeHgCl into biologically inert HgSe nanoparticles and Me2Hg via the formation of an unstable intermediate (MeHg)2Se (pathway I). However, under neutral conditions, in the absence of any base, ImOHSe facilitates the cleavage of the Hg–C bond of MeHgCl at room temperature (23 °C), leading

  我们显示具有N–CH 2 CH 2 OH取代基的基于N-甲基咪唑的selone Im OH Se具有通过两种不同的途径降解甲基汞的显着能力。在碱性条件下，Im OH Se通过形成不稳定的中间体（MeHg）2 Se来将MeHgCl转化为生物惰性的HgSe纳米颗粒和Me 2 Hg （途径I）。但是，在中性条件下，在没有任何碱的情况下，Im OH Se促进了室温下（23°C）MeHgCl的Hg–C键的裂解，导致形成稳定的裂解产物，即四配位单核汞化合物（Im OH Se）2HgCl 2和Me 2 Hg（途径II）。Im OH Se诱导的MeHgCl的Hg–C键断裂的初始速率几乎比Im Me Se观察到的初始速率高2倍。此外，我们表明，Im Y Se（Y = OH，Me）在室温下具有出色的使Me 2 Hg脱烷基化的能力。在酸性条件下，在过量的Im Y Se的存在下，挥发性和有毒的Me 2 Hg进一步分解为四配位单核汞化合物[（Im
• Practical and theoretical considerations for the determination of <i>δ</i> ¹³ C _VPDB values of methylmercury in the environment
  作者：Philip J.H. Dunn、Mine Bilsel、Adnan Şimşek、Ahmet Ceyhan Gören、Murat Tunç、Nives Ogrinc、Milena Horvat、Heidi Goenaga‐Infante

  DOI：10.1002/rcm.8453

  日期：2019.7.15

  Analytical methods that can identify the source and fate of mercury and organomercury compounds are likely to be useful tools to investigate mercury in the environment. Carbon isotope ratio analysis of methylmercury (MeHg) together with mercury isotope ratios may offer a robust tool to study environmental cycling of organomercury compounds within fish tissues and other matrices.

  可以确定汞和有机汞化合物的来源和归宿的分析方法可能是研究环境中汞的有用工具。甲基汞（MeHg）的碳同位素比分析以及汞同位素比可能为研究鱼组织和其他基质中有机汞化合物的环境循环提供强有力的工具。
• Synthesis, Structure, and Reactivity of O-Donor Ir(III) Complexes:  C−H Activation Studies with Benzene
  作者：Gaurav Bhalla、Xiang Yang Liu、Jonas Oxgaard、William A. Goddard、Roy A. Periana

  DOI：10.1021/ja051532o

  日期：2005.8.1

  water-stable alkyl and aryl analogues of (acac-O,O)2Ir(R)(L), R-Ir-L (acac-O,O = kappa2-O,O-acetylacetonate, -Ir- is the trans-(acac-O,O)2Ir(III) motif, R = CH3, C2H5, Ph, PhCH2CH2, L = Py) have been synthesized using the dinuclear complex [Ir(mu-acac-O,O,C3)-(acac-O,O)(acac-C3)]2, [acac-C-Ir]2, or acac-C-Ir-H2O. The dinuclear Ir (III) complexes, [Ir(mu-acac-O,O,C3)-(acac-O,O)(R)]2 (R = alkyl), show fluxional

  (acac-O,O)2Ir(R)(L), R-Ir-L（acac-O,O = kappa2-O,O-乙酰丙酮化物，-）的各种新的热空气和水稳定的烷基和芳基类似物Ir- 是反式-(acac-O,O)2Ir(III) 基序，R = CH3, C2H5, Ph, PhCH2CH2, L = Py) 已使用双核复合物 [Ir(mu-acac-O,O ,C3)-(acac-O,O)(acac-C3)]2、[acac-C-Ir]2 或 acac-C-Ir-H2O。双核 Ir (III) 配合物 [Ir(mu-acac-O,O,C3)-(acac-O,O)(R)]2 (R = 烷基)，显示出具有五坐标的通量行为，16通过解离途径形成电子复合物。吡啶加合物 R-Ir-Py 通过具有 Ph-Ir-Py 激活参数的解离机制进行简并 Py 交换（deltaH++ = 22.8 +/- 0.5 kcal/mol；deltaS++
• Preparation and vibrational spectra of tetra-n-propylammonium carbonyldichloro-organoplatinate(II) salts, and a comparison of their carbon-13 and platinum-195 nuclear magnetic resonance properties with those of organomercury compounds
  作者：Jane Browning、Peter L. Goggin、Robin J. Goodfellow、Nicholas W. Hurst、Leslie G. Mallinson、Martin Murray

  DOI：10.1039/dt9780000872

  日期：——

  but derivatives with R = But, C2H3, or C3H5 could not be obtained. Infrared and Raman spectra are reported and discussed. The 1H, 13C, and 1H-195Pt} INDOR spectra have been investigated. The behaviours of 1J(PtC) and δ(195Pt) are discussed with reference to the 13C parameters and δ(199Hg) of the mercury compounds, [HgX(R)](X = Cl, Br, I, or R).

  [NPr n 4 ] 2- [PrCl 2 R（CO）]（R = Me，Et，Pr n，Pr i，Bu n或Ph）盐是由[NPr n 4] 2- [具有HgR 2的Pt 2 Cl 4（CO）2 ] ，但不能获得R = Bu t，C 2 H 3或C 3 H 5的衍生物。报告和讨论了红外光谱和拉曼光谱。的1 H，13 C，和1 H- 195已经研究了Pt} INDOR光谱。参照汞化合物[HgX（R）]（X = Cl，Br，I或L）的13 C参数和δ（199 Hg），讨论了1 J（PtC）和δ（195 Pt）的行为。R）。

表征谱图