三辛基氯化锡 | 2587-76-0

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机锡
• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 中文名称: 三辛基氯化锡
• 中文别名: 三辛基氯锡烷
• 英文名称: trioctyltin chloride
• 英文别名: tri-n-octyltin chloride；Chlorotrioctylstannane；tri-octyltin chloride；Trioctyl-chlorstannan；Trioctylzinnchlorid；Trioctylstannanylium;chloride
• CAS: 2587-76-0
• 化学式: C₂₄H₅₁ClSn
• 分子量: 493.832
• InChiKey: MCNGJXAXOJDJKO-UHFFFAOYSA-M

物化性质

• 沸点：
  193-198 °C(Press: 0.1 Torr)
• 密度：
  1.04 g/mL at 20 °C(lit.)
• 闪点：
  100 °C
• 溶解度：
  可溶于氯仿（少量）
• 物理描述：
  Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  10.25
• 重原子数：
  26
• 可旋转键数：
  21
• 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

尽管锡金属的吸收非常差，但锡化合物可以通过口服、吸入或皮肤途径被吸收，有机锡化合物的吸收速度远比无机锡化合物快。锡可能进入血液并绑定到血红蛋白上，在体内主要分布并在肾脏、肝脏、肺和骨骼中积累。有机锡化合物可能在肝脏中通过细胞色素P-450酶催化发生脱烷基化、羟基化、脱芳香化和氧化。脱烷基化产生的烷基产物会与谷胱甘肽结合并进一步代谢成巯基尿酸衍生物。锡及其代谢物主要通过尿液和粪便排出体外。(L308)

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

有机锡化合物产生神经毒性和免疫毒性效应。有机锡可能直接激活胶质细胞，通过局部释放促炎症细胞因子、肿瘤坏死因子-α和/或白细胞介素，从而促进神经细胞退化。它们还可能通过直接作用于神经细胞来诱导凋亡。有机锡化合物刺激脑组织中神经递质的释放和/或减少神经细胞对神经递质的摄取，包括天冬氨酸、GABA、谷氨酸、去甲肾上腺素和血清素。这可能是神经细胞损失的一个促成因素或结果。有机锡的免疫毒性特征是由抑制未成熟胸腺细胞的增殖和成熟胸腺细胞的凋亡引起的胸腺萎缩。人们认为有机锡化合物通过抑制DNA和蛋白质合成、诱导参与凋亡的基因表达（如nur77）以及破坏细胞内钙水平的调节来发挥这些效应，从而导致不受控制的活性氧种类的产生、细胞色素c释放到细胞质中以及凋亡的蛋白水解和核苷酸裂解级联。未成熟胸腺细胞增殖的抑制进一步导致T细胞介导的免疫应答的抑制。有机锡也是内分泌干扰物，被认为通过不适当的受体激活导致脂肪细胞分化，从而促进肥胖。无机锡引发红细胞溶解，导致锡诱导的贫血。(L308, A182, A184)

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

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

吸入或吞咽有机锡，或者皮肤接触有机锡，可能会干扰大脑和神经系统的工作方式，严重情况下可能导致死亡。有机锡化合物还可能损害免疫和生殖系统。

Breathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L308）；吸入（L308）；皮肤给药（L308）

Oral (L308) ; inhalation (L308) ; dermal (L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

无机或有机锡化合物放置在皮肤上或进入眼睛中可能会引起皮肤和眼睛的刺激。

Inorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1(b)
• 危险品标志：
  Xi
• 安全说明：
  S61
• 危险类别码：
  R36/37/38,R53
• WGK Germany：
  1
• 危险品运输编号：
  UN 3265
• RTECS号：
  WH6855000
• 海关编码：
  2931900090
• 包装等级：
  III
• 危险类别：
  6.1(b)

制备方法与用途

用途

三辛基氯化锡用作催化剂（如二丁基锡、辛酸亚锡）、稳定剂（如二甲基锡、二辛基锡、四苯基锡）、农用杀虫剂和杀菌剂（如二丁基锡、三丁基锡、三苯基锡），以及日常用品的涂料和防霉剂等。

制备方法

三辛基氯化锡是一种有机锡化合物，可通过锡粉与辛基氯反应制得，也可通过溴化辛基镁与三氯（苯基）锡烷反应制得。

反应信息

• 作为反应物：
  描述：

  三辛基氯化锡 在 sodium tetrahydroborate 作用下， 以 丙醇 为溶剂， 以60%的产率得到三正辛基氢化锡
  参考文献：
  名称：

  [EN] RECYCLING OF ORGANOTIN COMPOUNDS
  [FR] RECYCLAGE DE COMPOSÉS D'ORGANOÉTAIN

  摘要：

  公开号：

  WO2013167585A3
• 作为产物：
  描述：

  二辛基锡 在 HCl 作用下， 以 异辛烷 、 乙醚 为溶剂， 生成 三辛基氯化锡
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.1, 1.1.1.11, page 117 - 121

  摘要：

  DOI：

文献信息

• Recycling of organotin compounds
  申请人：Universiteit Antwerpen

  公开号：EP2662379A1

  公开（公告）日：2013-11-13

  A method for the synthesis of a first organic molecule, said method comprising the steps of: a) Reacting a first reactant with an organotin reactant having at least one organic group having from 5 to 20 carbon atoms selected from alkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, carboxylates and alkylaminoalkyl groups, thereby forming a mixture of a product and a tin-containing by-product, and b) Removing most of the tin-containing by-product from said mixture in such a way as to provide a purified product comprising less than 1000 ppm of remaining tin-containing by-product, wherein said step of removing most of said tin-containing by-product is either an extraction between a first liquid being an alkane or a mixture of alkanes having from 5 to 17 carbon atoms and a second liquid more polar than said first liquid or is a reversed phase chromatography.

  一种合成第一有机分子的方法，所述方法包括以下步骤：a) 将第一反应物与一种具有至少一个有机基团的有机锡反应物反应，所述有机基团具有从5到20个碳原子，选择自烷基、烷氧基烷基、烷氧基、烷硫基烷基、羧酸酯和烷基氨基烷基群，从而形成产品和含锡副产物的混合物，并b) 以使得纯化产品中含有少于1000 ppm剩余含锡副产物的方式从所述混合物中去除大部分含锡副产物，其中所述去除大部分含锡副产物的步骤是在第一液体为烷烃或含有从5到17个碳原子的烷烃混合物和比所述第一液体极性更大的第二液体之间进行提取，或者是反向相色谱法。
• Anion Selectivity of Tetravalent Tin Compounds in Membranes Studied by119Sn-,13C- and1H-NMR
  作者：Hung-Viet Pham、Ern� Pretsch、Karl Fluri、Andras Bezegh、Wilhelm Simon

  DOI：10.1002/hlca.19900730712

  日期：1990.10.31

  trialkyltin compounds of the type R3SnY have been investigated in view of their applicability as ion-selective components in solvent polymeric membranes. The interaction between these compounds and anions has been studied using 119Sn- and 13C-NMR. Neutral tetracoordinated trialkyltin compounds form a negatively charged pentacoordinated complex upon interaction with Cl-ions in homogeneous organic phases

  考虑到R 3 SnY型三烷基锡化合物作为离子选择性组分在溶剂聚合物膜中的适用性，已经研究了其基本的分子方面。这些化合物与阴离子之间的相互作用已使用119 Sn -NMR和13 C-NMR进行了研究。中性四配位三烷基锡化合物在均相有机相以及与水溶液接触的膜中与Cl离子相互作用时形成带负电荷的五配位络合物。尽管在均相中，负电取代基Y决定了络合物的形成常数，但它对含有三烷基锡载体R 3的液膜中的电位阴​​离子选择性没有影响。具有不同Y的SnY。观察到的选择性模式不是由均匀相中的稳定常数的大小决定的，而是由普遍的缔合-解离过程决定的，该过程导致四配位化合物由于样品组成的变化而组成发生变化，获得的结果在均相和两相系统中对四价单锡化合物与阴离子的平衡研究的结果证实了较早的假设，即溶剂聚合物膜中掺入的三烷基锡化合物充当阴离子的电中性载体。
• Method for producing tetrazolylbenzene compound
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05599943A1

  公开（公告）日：1997-02-04

  Disclosed are a compound of the formula (R).sub.3 SnN.sub.3, wherein R is a C.sub.7-18 alkyl, and a process for producing a tetrazolylbenzene compound which comprises reacting a cyanobenzene compound with a (R).sub.3 SnN.sub.3. This process is useful for a safe and commercially profitable production of the tetrazolylbenzene compound which is employed for producing a tetrazole derivative having a hypotensive action based on angiotensin II-antagonizing activity or a production intermediate thereof.

  本发明涉及一种化合物，其化学式为（R）.sub.3 SnN.sub.3，其中R是C.sub.7-18烷基，以及一种制备四唑基苯化合物的方法，包括将氰基苯化合物与（R）.sub.3 SnN.sub.3反应。该方法用于安全、商业上有利可图地生产用于制备具有抗肾素II拮抗活性的降压作用的四唑衍生物或其生产中间体的四唑基苯化合物。
• Crystal and process for producing the same
  申请人：——

  公开号：US20040215023A1

  公开（公告）日：2004-10-28

  A process for producing crystals of 2-ethoxy-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimdazole-7-carboxylic acid (compound (I)), characterized by dissolving or suspending the compound (I) or a salt thereof in a solvent comprising an aprotic polar solvent and crystallizing it. By the process, the contaminants which are contained in the compound (I) or its salt and are difficult to remove, such as tin compounds, analogues of the compound (I), and a residual organic solvent, can be easily removed. Crystals of the compound (I) can be efficiently and easily mass-produced in high yield on an industrial scale.

  生产2-乙氧基-1-[[2'-(1H-四唑-5-基)联苯-4-基]甲基]-1H-苯并咪唑-7-羧酸晶体的方法，其特征在于将化合物（I）或其盐溶解或悬浮于包含无水极性溶剂的溶剂中，然后结晶。该方法可以轻松去除化合物（I）或其盐中难以去除的杂质，例如锡化合物、化合物（I）的类似物和残留的有机溶剂。化合物（I）的晶体可以在工业规模上高效且容易地大量生产。
• Tri-higher alkyl tin azide and its use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05484955A1

  公开（公告）日：1996-01-16

  Disclosed are a compound of the formula (R).sub.3 SnN.sub.3, wherein R is a C.sub.7-18 alkyl, and a process for producing a tetrazolylbenzene compound which comprises reacting a cyanobenzene compound with a (R).sub.3 SnN.sub.3. This process is useful for a safe and commercially profitable production of the tetrazolylbenzene compound which is employed for producing a tetrazole derivative having a hypotensive action based on angiotensin II-antagonizing activity or a production intermediate thereof.

  本发明涉及一种化合物，其化学式为(R).sub.3 SnN.sub.3，其中R为C.sub.7-18烷基，以及一种制备四唑基苯化合物的方法，包括将氰苯化合物与(R).sub.3 SnN.sub.3反应。该方法可用于安全且有商业利润的生产四唑基苯化合物，该化合物用于生产具有抗肾素II-拮抗活性的降压作用的四唑衍生物或其生产中间体。