1,1-双(三甲基硅氧基)乙烯 | 24697-35-6

• 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: 1,1-双(三甲基硅氧基)乙烯
• 英文名称: Bis(trimethylsilyl) ketene acetal
• 英文别名: ketene bis(trimethylsilyl) acetal；Bis-O-trimethylsilyl-ketenacetal；1,1-bis-trimethylsilyloxy-ethene；Trimethyl(1-trimethylsilyloxyethenoxy)silane
• CAS: 24697-35-6
• 化学式: C₈H₂₀O₂Si₂
• 分子量: 204.417
• InChiKey: QTLOQPVMBORRRD-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C (12 mmHg)
• 密度：
  0.8586 g/cm3
• 闪点：
  25 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090
• 储存条件：
  存于阴凉干燥处

SDS

Name:	1 1-Bis(trimethylsilyloxy)-ethene Material Safety Data Sheet
Synonym:	None Known
CAS:	24697-35-6

Section 1 - Chemical Product MSDS Name:1 1-Bis(trimethylsilyloxy)-ethene Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24697-35-6	1,1-Bis(trimethylsilyloxy)-ethene	100	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.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24697-35-6: 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: colorless to pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 50 deg C @ 12.00mmHg
Freezing/Melting Point: Not available.
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:
Molecular Formula: C8H20O2Si2
Molecular Weight: 204.42

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24697-35-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,1-Bis(trimethylsilyloxy)-ethene - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 24697-35-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24697-35-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24697-35-6 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：

  1,1-双(三甲基硅氧基)乙烯 在 四氯化硅 作用下， 生成 Bis-O-trimethylsilyl-trichlorsilyl-ketenacetal
  参考文献：
  名称：

  Rudakova,T.A. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 1982 - 1985

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 三甲基硅乙酸酯 生成 1,1-双(三甲基硅氧基)乙烯
  参考文献：
  名称：

  乙烯酮双（三烷基甲硅烷基）乙缩醛：合成，热解和光谱研究

  摘要：

  描述了两种高产率的合成方法，用于制备烷基，二烷基，芳基和二芳基乙烯酮双（三烷基甲硅烷基）缩醛。一种是通过α金属化的三甲基甲硅烷基羧酸盐与三甲基氯硅烷（TMCS）的反应，而另一种是通过羧酸与TMCS的二价阴离子的相互键合。环丙烷羧酸和TMCS的二价阴离子以90％的收率得到C-硅酸酯。交叉实验表明，二苯基乙烯酮双（三烷基甲硅烷基）缩醛热解为二苯基乙烯酮和双（三烷基甲硅烷基）醚在分子间进行。单取代的和二烷基酮烯（三甲基甲硅烷基）缩醛的热解得到了酮烯-酮缩醛的加成产物（III），其在溶剂分解时以高收率提供了β-酮酸。给出了许多化合物的NMR和质谱数据。

  DOI：

  10.1016/s0022-328x(00)90476-5

文献信息

• Novel heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators
  申请人：——

  公开号：US20030216463A1

  公开（公告）日：2003-11-20

  The present invention is directed to novel heteroatom containing tetracyclic derivatives, pharmaceutical compositions containing them, their use in the treatment and/or prevention of disorders mediated by one or more estrogen receptors and processes for their preparation. The compounds of the invention are useful in the treatment and/or prevention of disorders associated with the depletion of estrogen such as hot flashes, vaginal dryness, osteopenia and osteoporosis; hormone sensitive cancers and hyperplasia of the breast, endometrium, cervix and prostate; endometriosis, uterine fibroids, osteoarthritis and as contraceptive agents, alone or in combination with a progestogen or progestogen antagonist.

  本发明涉及包含杂原子的新型四环衍生物，包含它们的药物组合物，它们在治疗和/或预防由一个或多个雌激素受体介导的疾病中的应用，以及它们的制备过程。发明中的化合物在治疗和/或预防与雌激素耗竭相关的疾病中是有用的，如热潮红、阴道干涩、骨量减少和骨质疏松症；激素敏感性癌症和乳腺、子宫内膜、宫颈和前列腺的增生；子宫内膜异位症、子宫肌瘤、骨关节炎，并且作为避孕剂，单独使用或与孕激素或孕激素拮抗剂结合使用。
• Synthetic Studies toward the Tetrapetalones: Diastereoselective Construction of a Putative Intermediate
  作者：Wen-Ju Bai、Thomas R. R. Pettus

  DOI：10.1021/acs.orglett.7b03500

  日期：2018.2.16

  A strategy toward tetrapetalones was explored including a site-selective ethylenation of the silyl enol ether A to afford a quaternary stereocenter that serves in a stereogenic capacity. Regio- and diastereoselective reactions were observed in conjunction with the oxidative formation of cation B, which included subsequent selective formation of either carbon–oxygen or carbon–carbon bonds at the δ or

  已研究出一种针对四氢萘酮的策略，包括甲硅烷基烯醇醚A的位点选择性乙烯化，以提供具有立体生成能力的四级立体中心。观察到区域和非对映选择性反应与阳离子B的氧化形成有关，其中包括随后在7元环的δ或ζ位选择性形成碳-氧或碳-碳键。使用Stetter反应形成第四环。
• Metal reductions of malonates and oxalates. A covenient decarboxylation route for disubstituted malonates and synthesis of keten acetals
  作者：Yu-Neng Kuo、Francis Chen、C. Ainsworth、Jordan J. Bloomfield

  DOI：10.1039/c29710000136

  日期：——

  Alkali-metal reduction of disubstituted malonates or treatment of esters with base in the presence of trimethylchlorosilane gives high yields of the reactive disubstituted keten alkyl trimethylsilyl acetals, while diethyl oxalate, under similar conditions is reduced to 1,2-diethyl-1,2-bis(trimethylsilyloxy)ethylene.

  二取代丙二酸酯的碱金属还原或在三甲基氯硅烷存在下用碱处理酯类可得到高产率的反应性二取代缩酮烷基三甲基甲硅烷基缩醛，而草酸二乙酯在类似条件下可还原为1,2-二乙基-1,2-双（三甲基甲硅烷氧基）乙烯。
• Reactivity of pyridines bearing EWG with bis-(TMS)ketene acetals. Substituent-induced lactonization reaction
  作者：Alejandro Rivera-Hernández、Guillermo M. Chans、Henri Rudler、José G. López Cortés、R. Alfredo Toscano、Cecilio Álvarez-Toledano

  DOI：10.1016/j.tet.2014.01.044

  日期：2014.3

  The nucleophilic addition of bis-(TMS)ketene acetals to pyridines substituted by electron-withdrawing groups, activated with triflic anhydride, leads to their corresponding dihydropyridine carboxylic acids in a first instance. These acids can be efficiently turned into new bicyclic lactones by either of three different methods: first, bicyclic γ-lactones were successfully obtained by an unprecedented

  在三氟甲磺酸酐活化下，双-（TMS）乙烯酮缩醛亲核加成到被吸电子基团取代的吡啶上，得到它们相应的二氢吡啶羧酸。这些酸可以通过三种不同的方法有效地转化为新的双环内酯：首先，通过硅胶辅助的前所未有的迈克尔型开环过程成功地获得了双环γ-内酯。第二，通过NBS促进过程获得双环δ-溴内酯。第三，观察到新的羟基γ-螺内酯意外地自发形成。沿着本文介绍的工作，研究了这些内酯化反应的范围，局限性和区域选择性，从而证实了双（TMS）乙烯酮乙缩醛作为1,3-二亲核试剂在此类反应中的应用，
• Bis(trimethylsilyl)ketene Acetals as C,O-Dinucleophiles: One-Pot Formation of Polycyclic γ- and δ-Lactones from Pyridines and Pyrazines
  作者：Henri Rudler、Bernard Denise、Yiming Xu、Andrée Parlier、Jacqueline Vaissermann

  DOI：10.1002/ejoc.200500162

  日期：2005.9

  interaction with both nitrogen atoms, of polycyclic γ-lactones, a reaction formally reminiscent of the double nucleophilic addition of the same ketene acetals to (arene)tricarbonylchromium complexes. Most of the new structures were assigned through X-ray crystal structure determinations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  双（三甲基甲硅烷基）烯酮缩醛在化学计量量的氯甲酸甲酯存在下与吡啶、喹啉和异喹啉反应，以令人满意的产率得到相应的二氢吡啶-、二氢喹啉-和二氢异喹啉-取代的羧酸。加成反应的区域选择性和非对映选择性以及旋转异构体的存在或不存在都已确定。分离出的酸与过酸反应，通过分子内反应生成 β-羟基-δ-内酯。类似的内酯化也可以直接从氮杂芳族化合物与硅胶、碘或溴的一锅反应中产生。在这些情况下，产生了δ-内酯或β-卤代-δ-内酯。吡嗪在这些转变中的行为是奇特的，由于氯甲酸甲酯本身通过与两个氮原子的相互作用诱导多环γ-内酯的形成，这种反应形式上让人想起相同的烯酮缩醛与（芳烃）三羰基铬配合物的双亲核加成反应。大多数新结构是通过 X 射线晶体结构测定确定的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)