双(三甲基硅烷基)硒醚 | 4099-46-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 双(三甲基硅烷基)硒醚
• 中文别名: 双(三甲基硅基)硒
• 英文名称: bis(trimethylsilyl)selenide
• 英文别名: HMDSS；[Bis(trimethylsilyl)]selenide；trimethyl(trimethylsilylselanyl)silane
• CAS: 4099-46-1
• 化学式: C₆H₁₈SeSi₂
• 分子量: 225.34
• InChiKey: FKIZDWBGWFWWOV-UHFFFAOYSA-N

物化性质

• 熔点：
  -7°C
• 沸点：
  58-9°C/11mmHg
• 密度：
  0,9 g/cm3
• 闪点：
  59.6±18.7℃
• 溶解度：
  溶于Et2O和THF。

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  9
• 可旋转键数：
  2
• 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

• TSCA：
  No
• 海关编码：
  2931900090
• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥处。

SDS

Name:	[bis(Trimethylsilyl)] Selenide 98% Material Safety Data Sheet
Synonym:	Hexamethyldisilselenan
CAS:	4099-46-1

Section 1 - Chemical Product MSDS Name:[bis(Trimethylsilyl)] Selenide 98% Material Safety Data Sheet
Synonym:Hexamethyldisilselenan

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4099-46-1	bis(Trimethylsilyl)] Selenide	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.Moisture sensitive.
Potential Health Effects
Eye:
No information regarding eye irritation and other potential effects was found.
Skin:
No information regarding skin irritation and other potential effects was found.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated.
Chronic:
Chronic exposure to selenium may cause pallor, garlic breath, metallic taste, anemia, liver and spleen damage.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
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 immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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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.
Extinguishing Media:
Do NOT use water directly on fire. Use carbon dioxide or dry chemical.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Do not allow contact with water.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Keep under a nitrogen blanket.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4099-46-1: United Kingdom, WEL - TWA: (listed as selenium compounds): 0.1 mg TWA (except hydrogen selenide, as Se) United Kingdom, WEL - STEL: (listed as selenium compounds): 0.3 m STEL (except hydrogen selenide, as Se) United States OSHA: 0.2 mg/m3 TWA (as Se) (listed under Selenium compounds).
Belgium - TWA: (listed as selenium compounds): 0.2 mg/m3 VLE (as Japan: (listed as selenium compounds): 0.1 mg/m3 OEL (except SeH2 SeF6, as Se) Malaysia: (listed as selenium compounds): 0.2 mg/m3 TWA (as Se) Netherlands: (listed as selenium compounds): 0.1 mg/m3 MAC (as Se Russia: (listed as silica, amorphous): 1 mg/m3 TWA Spain: (listed as selenium compounds): 0.1 mg/m3 VLA-ED (except hydrogen selenide, as Se) Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: clear, colorless
Odor: Stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 31 deg C @ 2.00mm Hg
Freezing/Melting Point: -7 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9010g/cm3
Molecular Formula: C6H18SeSi2
Molecular Weight: 225.34

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, silicon dioxide, selenium/selenium oxides.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4099-46-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
bis(Trimethylsilyl)] Selenide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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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: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 20/21 When using do not eat, drink or smoke.
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4099-46-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4099-46-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4099-46-1 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

反应信息

• 作为反应物：
  描述：

  双(三甲基硅烷基)硒醚 在 碘 作用下， 以 间二甲苯 为溶剂， 以94%的产率得到碘代三甲硅烷
  参考文献：
  名称：

  Bis(trialkylsilyl) chalcogenides. 1. Preparation and reduction of group VIA oxides

  摘要：

  DOI：

  10.1021/jo00346a041
• 作为产物：
  描述：

  三甲基溴硅烷 在 seleno-aluminate 作用下， 反应 3.0h， 以62%的产率得到双(三甲基硅烷基)硒醚
  参考文献：
  名称：

  Drake, John E.; Glavincevski, Boris M.; Hemmings, Raymond T., Canadian Journal of Chemistry, 1980, vol. 58, # 20, p. 2161 - 2166

  摘要：

  DOI：
• 作为试剂：
  描述：

  二(五氟苯基)亚膦基氯化物 在 15-冠醚-5 、 双(三甲基硅烷基)硒醚 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以59%的产率得到tetrakis(pentafluorophenyl)diphosphanylselane
  参考文献：
  名称：

  氯膦与硫属化物的缩合反应

  摘要：

  开发了一种高产率且易于合成的二膦烷单硫属化合物（1 Ch （R））及其结构异构体二膦酰二氯烷（2 Ch （R）），其特征是氯膦（R 2 PCl）与硫属元素化钠（Na 2 Ch，Ch = S，Se，（Te））。优化的协议有选择地产生1 Ch （R）（R 2（Ch）PPR 2）或2 Ch （R）（Ch（PR 2）2）取决于取代基R的空间需求。提出了与不同反应结果一致的反应途径。中的应用1章（R）和2章（R）作为一类有趣的配体的示例性地由选定的过渡金属络合物的制备证明。

  DOI：

  10.1021/acs.inorgchem.5b02723

文献信息

• Bis(trimethylsilyl)selenide in the Selective Synthesis of β-Hydroxy, β-Mercapto, and β-Amino Diorganyl Diselenides and Selenides Through Ring Opening of Strained Heterocycles
  作者：Damiano Tanini、Alessandro Degl'Innocenti、Antonella Capperucci

  DOI：10.1002/ejoc.201403015

  日期：2015.1

  dialkyl diselenides and selenides is described through reaction of bis(trimethylsilyl)selenide with epoxides, thiiranes, and aziridines catalyzed by tetrabutylammonium fluoride. Selective formation of a wide variety of β-hydroxy, β-mercapto, and β-amino diselenides and selenides is achieved by controlling the reaction conditions in the regioselective attack of the silyl selenide onto the ring-strained

  通过双（三甲基甲硅烷基）硒化物与环氧化物、硫杂环丙烷和氮丙啶在四丁基氟化铵催化下的反应，描述了一种合成 β-取代的二烷基二硒化物和硒化物的新方法。选择性形成多种 β-羟基、β-巯基和 β-氨基二硒化物和硒化物是通过控制硒化甲硅烷对环应变杂环的区域选择性攻击的反应条件来实现的。所有反应都以高度区域选择性和对映体保守的方式发生，以良好到高产率提供标题化合物。测量硒 77 NMR 化学位移以验证 β 取代的二硒化物和硒化物的选择性形成。
• Phosphorus-Chalcogen Ring Expansion and Metal Coordination
  作者：Cameron M. E. Graham、Juuso Valjus、Taylor E. Pritchard、Paul D. Boyle、Heikki M. Tuononen、Paul J. Ragogna

  DOI：10.1021/acs.inorgchem.7b02217

  日期：2017.11.6

  The reactivity of 4-membered (RPCh)2 rings (Ch = S, Se) that contain phosphorus in the +3 oxidation state is reported. These compounds undergo ring expansion to (RPCh)3 with the addition of a Lewis base. The 6-membered rings were found to be more stable than the 4-membered precursors, and the mechanism of their formation was investigated experimentally and by density functional theory calculations

  报道了含+3氧化态磷的4元（RPCh）2环（Ch = S，Se）的反应性。这些化合物在添加路易斯碱的情况下经历扩环成（RPCh）3的过程。发现六元环比四元前体更稳定，并通过实验和密度泛函理论计算研究了它们的形成机理。计算工作确定了两个可能的机理，这些机理涉及次膦基硫属元素化物中间体，它们是一种游离物质，也可以通过合适的碱稳定。发现4元和6元环均与造币金属反应，得到相同的产物：（RPCh）3个环以三脚架方式从磷原子结合到金属中心。
• Stable -ESiMe₃ Complexes of Cu^I and Ag^I (E=S, Se) with NHCs: Synthons in Ternary Nanocluster Assembly
  作者：Mahmood Azizpoor Fard、Tetyana I. Levchenko、Carolyn Cadogan、William J. Humenny、John F. Corrigan

  DOI：10.1002/chem.201503320

  日期：2016.3.18

  their chemistry for the formation of ternary mixed‐metal chalcogenide nanoclusters, two sets of thermally stable, N‐heterocyclic carbene metal–chalcogenolate complexes of the general formula [(IPr)Ag−ESiMe3] (IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐ylidene; E=S, 1; Se, 2) and [(iPr2‐bimy)Cu−ESiMe3]2 (iPr2‐bimy=1,3‐diisopropylbenzimidazolin‐2‐ylidene; E=S, 4; Se, 5) are reported. These are prepared

  作为制备新的“金属仲硫氰酸盐”前体并发展其化学性质以形成三元混合金属硫属元素化物纳米团簇的努力的一部分，这两组热稳定的通式为[（IPr）Ag的N-杂环卡宾金属-硫属元素酸盐配合物-ESiMe 3 ]（IPr = 1,3-双（2,6-二异丙基苯基）咪唑啉-2-亚基; E = S，1 ; Se，2）和[（i Pr 2 -bimy）Cu-ESiMe 3 ] 2（i Pr 2 -bimy = 1,3-二异丙基苯并咪唑啉-2-亚基; E = S，4 ; Se，5）的报告。它们分别由相应的卡宾金属乙酸盐，[（IPr）AgOAc]和[（i Prbibimy）CuOAc]与E（SiMe 3）2在低温下反应制得。的反应[（IPR）的Ag-ESiMe 3 ] 1与汞（II），乙酸，得到杂金属配合物[（IPR）AGS} 2汞柱] 3含有两个（IPR）AGS -片段结合到汞柱中央II，代表汞-硫化银的混合配合物。[[
• Controlling the White‐Light Generation of [(RSn) ₄ E ₆ ]: Effects of Substituent and Chalcogenide Variation
  作者：Eike Dornsiepen、Florian Dobener、Sangam Chatterjee、Stefanie Dehnen

  DOI：10.1002/anie.201909981

  日期：2019.11.18

  blue-shifts are observed by introduction of cyclopentadienyl substituents, while the introduction of Se in the inorganic core can provoke a red-shift. These investigations disprove the initial assumption of an aromatic substituent being a necessary precondition; the precondition seems to be the presence of (cyclic) substituents providing enough electron density.

  一般成分[（RT）4 S6]（R =芳族取代基，T = Si，Ge，Sn）的金刚烷型有机锡硫族元素簇具有极高的非线性光学特性，可导致高度定向的白光产生（WLG）在用红外激光二极管照射时。但是，该机制尚不清楚。现在，制备了一系列化合物[（RSn）4 E6]（R =苯基，环戊二烯基，环己基，苄基，CH2 （C6 H4）CO2 Et； E = S，Se），并对其非线性进行了研究。光学性质。除了晶体[（BnSn）4 S6]以外，所有这些化合物均显示出具有相似发射光谱的WLG；所有化合物均具有相同的发射光谱。通过引入环戊二烯基取代基可以观察到轻微的蓝移，而在无机核中引入Se可以引起红移。这些研究证明了芳香取代基是必要前提的最初假设。前提条件似乎是提供足够电子密度的（环状）取代基的存在。
• Kupferchalkogenid-Clusterverbindungen mit Brom-funktionalisierter Ligandenhülle
  作者：Robert Langer、Linda Wünsche、Dieter Fenske、Olaf Fuhr

  DOI：10.1002/zaac.200900233

  日期：2009.8.28

  Copper Chalcogenide Cluster Compounds with Nitro-functionalized Ligand Shell Three new copper chalcogenide cluster molecules, [Cu4(SC6H4NO2)4(PPh3)4] (1), [Cu4(SC6H4NO2)2(OAc)2(PPh3)4] (2), and [Cu22Se6(SC6H4NO2)10(PPh3)8] (3), have been synthesized and characterized by single crystal X-ray structure analysis. 1 and 2 were prepared from the reactions of Cu(OAc) and HSC6H4NO2 in the presence of PPh3

  具有硝基官能化配体壳的铜硫属化物簇化合物 三种新的铜硫属化物簇分子，[Cu4(SC6H4NO2)4(PPh3)4] (1), [Cu4(SC6H4NO2)2(OAc)2(PPh3)4] (2) , 和 [Cu22Se6(SC6H4NO2)10(PPh3)8] (3)，已经合成并通过单晶 X 射线结构分析表征。图 1 和图 2 是由 Cu(OAc) 和 HSC6H4NO2 在 PPh3 存在下反应制备的，具有类似的“椅子”结构，其中两个铜原子呈三角配位，两个原子呈四面体配位。配体的硝基不与任何金属原子配位，而是位于簇分子有机壳的表面。在 2 和 Se(SiMe3)2 之间的进一步反应中，簇 3 结晶。3 的晶体包含大约 16.5 分子 THF 每个分子式单位。该合成展示了使用这些“小”铜硫族化物簇作为合成更大物种的前体化合物。类似于 1 和 2 的非官能化化合物通常是非常苍白甚至无色的晶体。