二辛基锡 | 3542-36-7

• 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 - 有机金属化合物 - 有机过渡后金属化合物
• 中文名称: 二辛基锡
• 中文别名: 二正辛基锡二氯化物；二辛基二氯化锡
• 英文名称: di-n-octyltin dichloride
• 英文别名: Dioctylzinndichlorid；Di-n-octyl-dichlor-stannan；dioctyldichlorotin；dioctyl tin dichloride；Di-n-octyl-zinn(IV)-dichlorid
• CAS: 3542-36-7
• 化学式: C₁₆H₃₄Cl₂Sn
• 分子量: 416.062
• InChiKey: SBOSGIJGEHWBKV-UHFFFAOYSA-L

物化性质

• 熔点：
  46-48°C
• 沸点：
  175°C 1mm
• 密度：
  1,175 g/cm3
• 闪点：
  204°C
• 暴露限值：
  ACGIH: TWA 0.1 mg/m3; STEL 0.2 mg/m3 (Skin)NIOSH: IDLH 25 mg/m3; TWA 0.1 mg/m3
• 物理描述：
  OtherSolid, Liquid
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  19
• 可旋转键数：
  14
• 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。这可能是神经细胞丢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（如nur77）的表达以及破坏细胞内钙水平的调节来发挥这些作用，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酸酶级联。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

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
• 安全说明：
  S26,S35,S36/37/39
• 危险类别码：
  R36/37/38,R48/20/22
• 海关编码：
  2931900090
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  3146
• 储存条件：
  常温、避光、通风干燥处，密封保存。

反应信息

• 作为反应物：
  描述：

  二辛基锡 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 dioctylstannane
  参考文献：
  名称：

  Metal-Catalyzed Dehydropolymerization of Secondary Stannanes to High Molecular Weight Polystannanes

  摘要：

  The first high molecular weight polystannanes, H(SnR(2))(n)H (R = (n)Bu, (n)Hex, (n)Oct), result from dehydropolymerization of secondary stannanes R(2)SnH(2) by zirconocene catalysts. Good catalysts include zirconocenes based on both CpCp*Zr (Cp* = eta(5)-C(5)Me(5)) and Cp(2)Zr fragments, and the most active catalyst with respect to production of high molecular weight polystannanes was Me(2)C(eta(5)-C5H4)(2)Zr[Si(SiMe(3))(3)]Me. The latter catalyst produced H(Sn(n)Bu(2))(n)H chains (M(w)/M(n) = 66 900/20 300) that were contaminated by ca. 18% (by weight) low molecular weight cyclic oligomers. Lower molecular weights resulted from dehydropolymerizations of Me(2)SnH(2), PhMeSnH(2), and Ph(2)SnH(2). At room temperature, H(SnR(2))(n)H (R alkyl group) polystannanes have lambda(max) values at ca. 380-400 nm, attributed to sigma --> sigma* transitions. Thermal gravimetric analyses on the polystannanes reveal that these polymers are as thermally stable as related poly(dialkylsilane)s and have onset temperatures for thermal decomposition in the range 200-270 degrees C, under both nitrogen and air. The H(Sn(n)Bu(2))(n)H polymer has been shown to be a good precursor to SnO2, as shown by bulk pyrolysis in air (ceramic yield: 56%). Preliminary results also indicate that these polymers may be useful as precursors to elemental tin. The polystannanes are photosensitive, and their photobleaching behavior has been characterized by UV-vis spectrometry and Sn-119 NMR spectroscopy, which demonstrated that H(Sn(n)Bu(2))(n)H is photochemicaly depolymerized to a 2:1 mixture of cyclo-(Sn(n)Bu(2))(5) and cyclo-(Sn(n)Bu(2))(6). The polymers H(Sn(n)Hex(2))(n)H and H(Sn(n)Oct(2))(n)H exhibit thermochromic behavior which is visibly evident as a discoloration from yellow to colorless upon warming above room temperature. This reversible behavior is associated with an abrupt change in lambda(max) (e.g., from 402 to 378 nm for films of H(Sn(n)Oc(2))(n)H) and a phase change at ca. 40 OC (by differential scanning calorimetry). Thin films of H(Sn(n)Bu(2))(n)H and H(Sn(n)Oct(2))(n)H on glass slides were doped by exposure to SbF5 vapor to conductivities of 10(-2) and 0.3 S cm(-1), respectively. Preliminary experiments suggest that the dehydropolymerization occurs by a sigma-bond metathesis mechanism involving four-center transition states. A previous report on production of high molecular weight poly(dibutylstannane) by the reductive coupling of (n)Bu(2)SnCl(2) by Na/15-crown-5 was reinvestigated and found to produce only low molecular weight material with M(w)/M(n) = 2400/ 1200.

  DOI：

  10.1021/ja00145a001
• 作为产物：
  描述：

  四正辛基锡 在 HgCl₂ 作用下， 以 乙醇 为溶剂， 生成 二辛基锡
  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：
• 作为试剂：
  描述：

  硫代氯甲酸苯酯 、 alpha-d-吡喃半乳糖苷甲酯 在 1,2,2,6,6-pentamethylpiperidine 、 四丁基碘化铵 、 二辛基锡 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以90%的产率得到methyl 3-O-phenoxythiocarbonyl-α-L-fucopyranoside
  参考文献：
  名称：

  JP5669643

  摘要：

  公开号：

文献信息

• 双（S,S-二氧-二苯并噻吩）并五元环化合物及 其制备方法与应用
  申请人：华南理工大学

  公开号：CN105017302B

  公开（公告）日：2019-06-18

  本发明公开双（S,S‑二氧‑二苯并噻吩）并五元环化合物及其制备方法与应用。所述双S,S‑二氧二苯并噻吩并五元环中双砜基的存在更加有利于提高分子的电子亲和势。在五元环上引入烷基链可以显著改善单体在有机溶剂中的溶解性。化合物的平面共轭性较好，有利于载流子的传输。化合物分子内存在较强的D‑A相互作用赋予材料较好的荧光性。双S,S‑二氧‑二苯并噻吩并五元环化合物通过取代反应、Suzuki偶联、闭环反应和氧化反应等常用有机化学反应合成得到。化合物在有机溶剂中有良好的溶解性，适合于溶液加工。在有机发光显示、有机光伏电池以及有机场效应管领域有着广泛的应用前景。
• 119Sn mössbauer, IR, 1H NMR spectroscopic and thermal decomposition studies on organotin(IV) adducts with glycylglycine
  作者：Lorenzo Pellerito、M.Teresa Lo Giudice、G.C. Stocco、John D. Donaldson、Susan M. Grimes、Peter J. Smith

  DOI：10.1016/s0277-5387(00)86692-9

  日期：1985.1

  The complexes R2SnCl2·(H2glygly), (H2glygly = glycylglycine) (R = Me, Bun, Octn, Ph) and RSnCl3·(H2glygly)

  R 2 SnCl 2 ·（H 2 glygly），（H 2 glygly =甘氨酰甘氨酸）（R = Me，Bu n，Oct n，Ph）和RSnCl 3 ·（H 2 glygly）
• The synthesis and tin-119m mössbauer spectra of some diorganotin dihalide and dipseudohalide complexes with nitrogen- and oxygen-donor ligands
  作者：Alan J. Crowe、Peter J. Smith

  DOI：10.1016/s0022-328x(00)85834-9

  日期：1982.1

  The synthesis and 119mSn Mössbauer spectra of 114 complexes of the type R2SnX2, L2 (R  Me, Et, n-Pr, n-Bu, n-Oct, Ph, Bz; X  F, Cl, Br, I, NCS; L2  2 monodentate or 1 bidentate O- or N-donor ligand(s)), 74 of which are new, are reported. The majority of the complexes are isostructural, having an octahedral trans-R2SnX4 geometry about tin, whilst five of the diphenyltin complexes (R  Ph; X  Cl;

  合成和119米的类型R的114个络合物的Sn穆斯堡尔谱2 SNX 2，L 2（RME等，正PR，正丁基，正-十月中，Ph，BZ; X氟，氯，溴，I，NCS，L 2 2单齿或二齿1 O-或N-供配体（S）），其中74个是新的，则报告。大部分复合物是同构的，具有八面体反式-R 2 SNX 4几何约锡，而二苯基复合物5（RPh值; X氯，L 2 AMP，Nphen; XNCS，L 2  bipy，phen，TMphen）采用顺式-R 2 SnX 4八面体结构。
• Potentially bioactive organotin(IV) compounds: Synthesis, characterization, in vitro bioactivities and interaction with SS-DNA
  作者：Muhammad Sirajuddin、Saqib Ali、Vickie McKee、Manzar Sohail、Hammad Pasha

  DOI：10.1016/j.ejmech.2014.07.028

  日期：2014.9

  six-coordinate geometry. The ligand and its complexes (1–14) were screened for their antimicrobial, antitumor, cytotoxic and antileishmanial activities and found to be biologically active. The ligand and its complexes bind to DNA via intercalative interactions resulting in hypochromism and minor bathochromic shifts as confirmed by UV–visible spectroscopy. Based on in vitro studies such as the potato

  十四种具有通式R 2 SnL 2或R 3 SnL的新有机锡（IV）配合物，其中R = CH 3，C 2 H 5，C 4 H 9，C 6 H 5，C 6 H 11，CH 2 -C 6 H 5，合成C（CH 3）3，C 8 H 17和L = N-[（2-甲氧基苯基）]-4-氧代-4- [氧]丁酰胺并通过元素分析，FT-IR，NMR（1 H，13 C和119Sn），质谱和单晶X射线结构分析。四种三有机锡（IV）配合物（R 3 SnL，R = CH 3，C 2 H 5，C 4 H 9，CH 2 –C 6 H 5）的晶体学数据表明，锡具有近似三角双锥体的几何形状，R基团位于三角平面。配体L的羧酸基桥接相邻的锡原子，从而形成聚合物链。对于二有机锡（IV）衍生物，根据光谱证据提出了锡原子处的六坐标几何结构。配合物7中的Me–Sn–Me键角由2 J确定[ 119 Sn– 1 H]值为166.3°，位于六坐标几何范围内。筛选了配体及其配合物（1
• The interaction of organotin(iv) acceptors with 1,4-bis(5-hydroxy-1-phenyl-3-methyl-1H-pyrazol-4-yl)butane-1,4-dioneCoordination chemistry of bis(pyrazolones): a rational design of nuclearity tailored polynuclear complexes. Part 2.22
  作者：Claudio Pettinari、Fabio Marchetti、Riccardo Pettinari、Augusto Cingolani、Andrei Drozdov、Sergei Troyanov

  DOI：10.1039/b106665j

  日期：2002.1.9

  From the interaction of organotin(IV) halides SnR2Cl2 with 1,4-bis(5-hydroxy-1-phenyl-3-methyl-1H-pyrazol-4-yl)butane-1,4-dione (Q2QH2) in methanol in the presence of base the complexes [SnR2(Q2Q)] (1: R = isobutyl (Bui); 2: R = n-octyl (Ot); 3: R = n-dodecyl (Do)) have been synthesised. The reaction between equimolar quantities of R2SnO and Q2QH2 in toluene yields the dinuclear derivatives [SnR2(Q2Q)]24

  从有机锡（IV）卤化物SnR 2 Cl 2与1,4-双（5-羟基-1-苯基-3-甲基-1 H-吡唑-4-基）丁烷-1,4-二酮（Q2QH 2）在碱存在下于甲醇中的络合物[SnR 2（Q2Q）]（1：R =异丁基（Bu i）; 2：R =正辛基（Ot）; 3：R =正十二烷基（Do） ）已综合。等摩尔量的R 2 SnO和Q2QH 2在甲苯中的反应生成双核衍生物[SnR 2（Q2Q）] 2 4（R = Me）和5（R = Bu n）在溶液中具有顺式-R 2 Sn构型，而在KOH存在下，由Q2QH 2与SnMe 2 Cl 2在CH 3 OH中的反应，形成不溶的可能为多核的异构体形式4。Q 2 QH 2和（R 3 Sn）2 O之间的反应产生衍生物[（SnR 3）2（Q2Q）]（6：R ＝ Bu n；7：R ＝ Ph）。6与水反应生成水络合物[（SnBu n 3）2（Q2Q）（H2 O）] 8。已经确定了[SnBu