氘代三正丁基锡 | 6180-99-0

• 物质功能分类: 化学试剂 - 氘代试剂
• 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: 氘代三正丁基锡
• 英文名称: tributyltin deuteride
• 英文别名: tri-n-butyltin deuteride；tributylstannane-d；Tri-n-Butylzinndeuterid；Tributylzinndeuterid；tributyl(deuterio)stannane
• CAS: 6180-99-0
• 化学式: C₁₂H₂₈Sn
• 分子量: 292.056
• InChiKey: DBGVGMSCBYYSLD-RCUQKECRSA-N

物化性质

• 沸点：
  65 °C (0.6 mmHg)
• 密度：
  1.082 g/mL at 25 °C(lit.)
• 闪点：
  104 °F
• 溶解度：
  苯、氯仿、二氯甲烷（少量溶解）、乙酸乙酯（少量溶解）
• 稳定性/保质期：
  常温常压下，这是一种稳定的无色液体。

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  13
• 可旋转键数：
  9
• 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

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T,N
• 安全说明：
  S35,S36/37/39,S45,S60,S61
• 危险类别码：
  R48/23/25,R36/38,R21,R50/53,R25
• WGK Germany：
  3
• 海关编码：
  28459000
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 1993 3/PG 3
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

Name:	Tributyltin deuteride Material Safety Data Sheet
Synonym:	Tri-n-butyltin deuteride
CAS:	6180-99-0

Section 1 - Chemical Product MSDS Name:Tributyltin deuteride Material Safety Data Sheet
Synonym:Tri-n-butyltin deuteride

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6180-99-0	Tributyltin deuteride	96	unlisted

Hazard Symbols: T N
Risk Phrases: 10 21 25 36/38 48/23/25 50/53

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Harmful in contact with skin. Toxic if swallowed.
Irritating to eyes and skin. Toxic : danger of serious damage to health by prolonged exposure through inhalation and if swallowed.
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.Moisture sensitive.Air sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
The critical effect of tributyltin compounds in rats is on the immune system (ACGIH 7th Edition Documentation of the TLVs).

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT get water inside containers. Do NOT use straight streams of water.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.
Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Use only with adequate ventilation. Keep away from heat, sparks and flame. Avoid breathing vapor or mist.
Storage:
Keep away from sources of ignition. Flammables-area. Keep refrigerated. (Store below 4C/39F.) Do not expose to air. Store protected from moisture. Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels below recommended exposure limits. Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Exposure Limits CAS# 6180-99-0: United Kingdom, WEL - TWA: (listed as tin organic compounds): 0.1 mg/m3 TWA (except cyhexatin, as Sn) United Kingdom, WEL - STEL: (listed as tin organic compounds): 0.
mg/m3 STEL (except cyhexatin, as Sn) United States OSHA: 0.1 mg/m3 TWA (as Sn) (listed under Tin orga compounds).
Belgium - TWA: (listed as tin organic compounds): 0.1 mg/m3 VLE ( Sn) Belgium - STEL: (listed as tin organic compounds): 0.2 mg/m3 VLE Sn) France - VME: (listed as tin organic compounds): 0.1 mg/m3 VME (a Sn) France - VLE: (listed as tin organic compounds): 0.2 mg/m3 VLE (a Sn) Germany: (listed as tin organic compounds): 0.1 mg/m3 VME (as Sn) Germany: (listed as tin organic compounds): Skin absorber Malaysia: (listed as tin organic compounds): 0.1 mg/m3 TWA (as Sn Netherlands: (listed as tin organic compounds): 0.2 mg/m3 STEL (a Sn) Netherlands: (listed as tin organic compounds): 0.1 mg/m3 MAC (as Spain: (listed as tin organic compounds): 0.1 mg/m3 VLA-ED (as Sn Spain: (listed as tin organic compounds): 0.2 mg/m3 VLA-EC (as Sn Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless to very faint yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 65 deg C @ .60mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 39 deg C ( 102.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.08 g/cm3
Molecular Formula: C12H27DSn
Molecular Weight: 292.06

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Ignition sources, moisture, exposure to air, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, tin/tin oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6180-99-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tributyltin deuteride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: FLAMMABLE LIQUID, TOXIC, N.O.S.*
Hazard Class: 3 (6.1)
UN Number: 1992
Packing Group: III
IMO
Shipping Name: FLAMMABLE LIQUID, TOXIC, N.O.S.
Hazard Class: 3.3 (6.1)
UN Number: 1992
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE LIQUID, TOXIC, N.O.S.
Hazard Class: 3 (6.1)
UN Number: 1992
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T N
Risk Phrases:
R 10 Flammable.
R 21 Harmful in contact with skin.
R 25 Toxic if swallowed.
R 36/38 Irritating to eyes and skin.
R 48/23/25 Toxic : danger of serious damage to
health by prolonged exposure through inhalation and if
swallowed.
R 50/53 Very toxic to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
Safety Phrases:
S 35 This material and its container must be
disposed of in a safe way.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
S 60 This material and its container must be
disposed of as hazardous waste.
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 6180-99-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6180-99-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6180-99-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

TBTH的氘代类似物主要用于在自由基参与的情况下引入氘，并应用于物理化学研究。

反应信息

• 作为反应物：
  描述：

  氘代三正丁基锡 在 catalyst: azoisobutyronitrile 作用下， 以 甲苯 为溶剂， 以67%的产率得到methyl 2-benzamido-2-deuterioacetate
  参考文献：
  名称：

  缩水甘油基当量与2-官能化烯丙基锡烷的反应

  摘要：

  2-溴-N-苯甲酰基甘氨酸甲酯与2-官能化的烯丙基锡烷试剂在自由基条件下的反应提供了一种以高收率获得α-烷基化氨基酸的新途径，这可以通过容易地合成4-亚甲基谷氨酸来举例说明。

  DOI：

  10.1039/c39880001030
• 作为产物：
  描述：

  三丁基氧化锡 生成 氘代三正丁基锡
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.2.1.1, page 38 - 56

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯甲醇 在 4-二甲氨基吡啶 、 水 、 三乙胺盐酸盐 、 氘代三正丁基锡 、 C₄₈H₆₄Cl₂N₂O₂Ti 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 78.0h， 生成
  参考文献：
  名称：

  双核钛(III)催化环氧化物的自由基型动力学拆分用于对映选择性合成顺式缩水甘油酯

  摘要：

  缩水甘油酯是合成化学中的关键成分，与简单的环氧化物相比，缩水甘油酯具有增强的多功能性，可针对多种分子靶标进行定制。尽管在反式和三取代缩水甘油酯的不对称合成方面已经取得了相当大的进展，但实现顺式缩水甘油酯的对映选择性制备仍然是一个长期存在的挑战。在这里，我们展示了一种选择性可预测的模块化平台，用于通过新型双核（salen）钛（III）催化的自由基型动力学拆分（KR）方法来不对称合成顺式缩水甘油酯。这种自由基 KR 方案在温和条件下运行，并表现出广泛的底物范围，促进具有高水平区域选择性和对映选择性的烷基和芳基取代的顺式缩水甘油酯的合成，以及代表具有合成价值的基序的羟基酯副产物。这项研究对应用于环氧化物的自由基型 KR 进行了独特的探索，有效克服了环氧化物化学中通常采用的传统亲核型方法所固有的空间挑战。

  DOI：

  10.1021/jacs.4c03346

文献信息

• One‐Step Synthesis of Dendritic Highly Branched Polystyrenes by Organotellurium‐Mediated Copolymerization of Styrene and a Dienyl Telluride Monomer
  作者：Yangtian Lu、Shigeru Yamago

  DOI：10.1002/anie.201814566

  日期：2019.3.18

  Dendritic highly branched polystyrenes (HB‐PSts) were prepared by a one‐step copolymerization of dienyl telluride 6 and St in the presence of organotellurium chain transfer agent 2. The molecular weight (MW), dendritic generation, and branching density were easily controlled by the ratio of 2 to 6 to styrene (St) with maintaining monodispersity. The branching efficiency estimated by a deuterium‐labeling

  树枝状高支化聚苯乙烯（HB-PSts）是通过在有机碲链转移剂2的存在下，将二烯基碲化物6和St一步共聚而制备的。分子量（MW），树状生成和支化密度很容易通过保持苯乙烯的单分散度与苯乙烯（St）的比例为2至6来控制。氘标记实验估计的分支效率表明，6定量（> 95％）作为分支点。根据端基向to衍生物的转化确定，端基保真度很高（约90％）。HP-聚苯乙烯的本征粘度显着低于线性聚苯乙烯，并且很容易通过支化数和支化密度进行调节。该方法适用于各种官能团，氯和乙酰氧基取代的苯乙烯也用作共聚单体。linear嵌段共聚物也从线性PSt开始作为大分子引发剂合成。
• Heterobimetallic Control of Regioselectivity in Alkyne Hydrostannylation: Divergent Syntheses of α- and (<i>E</i>)<i>-</i>β<i>-</i>Vinylstannanes via Cooperative Sn–H Bond Activation
  作者：Li-Jie Cheng、Neal P. Mankad

  DOI：10.1021/jacs.9b00068

  日期：2019.2.27

  terminal alkynes under mild conditions, with Markovnikov/anti-Markovnikov selectivity controlled by the Cu/M pairing. By using the MeIMesCu-FeCp(CO)2 catalyst, a variety of α-vinylstannanes were produced from simple alkyl-substituted alkynes and Bu3SnH in high yield and good regioselectivity; these products are challenging to access under mononuclear metal-catalyzed hydrostannylation conditions. In addition

  通过可调异双金属 (NHC)Cu-[MCO] 催化剂（[MCO] = FeCp(CO)2 或 Mn(CO)5）协同 Sn-H 键活化氢锡烷 (Bu3SnH) 能够在温和条件下催化氢化锡烷基化末端炔, 马尔科夫尼科夫/反马尔科夫尼科夫选择性由铜/M 配对控制。通过使用MeIMesCu-FeCp(CO)2催化剂，以简单的烷基取代炔烃和Bu3SnH为原料，以高产率和良好的区域选择性制备了多种α-乙烯基锡烷；这些产品在单核金属催化氢化锡烷基化条件下难以获得。此外，在 Cu/Fe 催化条件下，芳基取代的炔烃观察到反向区域选择性，得到 (E)-β-乙烯基锡烷作为主要产物。另一方面，通过使用 IMesCu-Mn(CO)5 催化剂，由伯、仲和叔烷基取代的炔烃制备了多种 (E)-β-乙烯基锡烷，因此证明了由 Cu/Fe 与 Cu/Mn 配对控制的炔烃氢化锡烷基化的不同区域选择性。这两种方法都适用于克级乙烯基
• Organometallic chemistry under high pressure: trialkyltin hydride addition to unsaturated systems
  作者：A. Rahm、M. Degueil-Castaing、M. Pereyre

  DOI：10.1016/s0022-328x(00)87648-2

  日期：1982.6

  The influence of high pressure (10–14 kbars) on the reaction of tin hydrides with alkenes and ketones has been investigated and a marked increase of yields generally was observed. For cyclopropyl- and cyclobutyl-alkenes, adducts were formed with retention of the rings. The stereochemical outcomes of the reactions were modified.

  已经研究了高压（10–14 kbars）对氢化锡与烯烃和酮反应的影响，并且通常观察到产率显着提高。对于环丙基和环丁基烯烃，在保留环的情况下形成加合物。反应的立体化学结果被修改。
• Reversible Formation of Alkyl Radicals at [Fe₄S₄] Clusters and Its Implications for Selectivity in Radical SAM Enzymes
  作者：Alexandra C. Brown、Daniel L. M. Suess

  DOI：10.1021/jacs.0c05590

  日期：2020.8.19

  All kingdoms of life use the transient 5'-deoxyadenosyl radical (5'-dAdo•) to initiate a wide range of difficult chemical reactions. Because of its high reactivity, the 5'-dAdo• must be generated in a controlled manner to abstract a specific H atom and avoid unproductive reactions. In radical S-adenosylmethionine (SAM) enzymes, the 5'-dAdo• is formed upon reduction of SAM by an [Fe4S4] cluster. How

  所有生命王国都使用短暂的 5'-脱氧腺苷基 (5'-dAdo•) 来引发各种困难的化学反应。由于其高反应性，必须以受控方式生成 5'-dAdo• 以提取特定的 H 原子并避免非生产性反应。在自由基 S-腺苷甲硫氨酸 (SAM) 酶中，5'-dAdo• 是在 SAM 被 [Fe4S4] 簇还原后形成的。这个过程如何发生以及这些酶控制 5'-dAdo• 反应性的机制才刚刚开始被理解。一种在 [Fe4S4] 簇和 5'-dAdo 基团之间具有 Fe-C 键的有机金属中间体最近被表征并显示出能够产生底物自由基，大概是通过 Fe-C 键均裂。这种反应性对于 Fe-S 簇来说是前所未有的，尚不清楚这种有机金属中间体如何影响自由基 SAM 酶的催化作用。在这里，我们表明，当烷基化的 Fe 位点具有合适的配位数时，合成的 [Fe4S4]-烷基簇会发生 Fe-C 键均裂，为自由基 SAM 酶中有机金属物种的
• Binuclear platinum(II) photochemistry. Rates of hydrogen atom transfer from organometallic hydrides to electronically excited Pt2(P2O5H2)44-
  作者：Antonin Vlcek、Harry B. Gray

  DOI：10.1021/ja00235a051

  日期：1987.1

  dsigma*psigma excited states of d/sup 8/-d/sup 8/ binuclear complexes (/sup 3/M/sub 2/*, M = Rh, Ir, Pt) are readily oxidized by one-electron acceptors. A related but largely unexplored reaction for these /sup 3/M/sub 2/* states is hydrogen atom abstraction, RH + /sup 3/M/sub 2/* ..-->.. R/sup ./ + /sup ./M/sub 2/H, a step that was proposed by Roundhill to be a primary process in the Pt/sub 2/-photocatalyzed

  先前的研究已经确定，d/sup 8/-d/sup 8/ 双核复合物 (/sup 3/M/sub 2/*, M = Rh, Ir, Pt) 的三重 dsigma*psigma 激发态很容易被氧化单电子受体。这些 /sup 3/M/sub 2/* 状态的一个相关但大部分未探索的反应是氢原子抽象，RH + /sup 3/M/sub 2/* ..-->.. R/sup ./ + / sup ./M/sub 2/H，Roundhill 提出的一个步骤是 Pt/sub 2/-光催化异丙醇转化为丙酮和二氢的主要过程（Pt/sub 2/ = Pt/sub 2 /(P/sub 2/O/sub 5/H/sub 2/)/sub 4//sup 4 -/)。Roundhill 提议的支持来自他们实验室的工作，该工作表明 /sup 3/Pt/sub 2/* 将从大量不同的底物中提取氢原子。由于氢原子转移在碳氢化合物和