2-(三甲基甲硅烷甲基)丙烯酸乙酯 | 74976-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(三甲基甲硅烷甲基)丙烯酸乙酯
• 中文别名: 2-(三甲硅烷基甲基)丙烯酸乙酯；乙基2-(三甲基甲硅烷基甲基)丙烯酸酯
• 英文名称: ethyl 2-(trimethylsilylmethyl)acrylate
• 英文别名: ethyl 2-(trimethylsilanylmethyl)acrylate；(2-Ethoxycarbonylallyl)-trimethylsilane；ethyl 2-methylene-3-(trimethylsilyl)propionate；ethyl (2-trimethylsilylmethyl)-prop-2-enoate；ethyl 2-(trimethylsilylmethyl)prop-2-enoate
• CAS: 74976-84-4
• 化学式: C₉H₁₈O₂Si
• mdl: MFCD00075508
• 分子量: 186.326
• InChiKey: HSEYTIDQGJXPIF-UHFFFAOYSA-N

物化性质

• 沸点：
  70-72 °C/10 mmHg (lit.)
• 密度：
  0.897 g/mL at 25 °C (lit.)
• 闪点：
  140 °F

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  3.2
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 1993
• 海关编码：
  2931900090
• 包装等级：
  III
• 危险类别：
  3.2
• 安全说明：
  S26,S36
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Ethyl 2-(trimethylsilylmethyl)acrylate
CAS-No. : 74976-84-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 2-(Trimethylsilylmethyl)acrylic acid ethyl ester
Ethyl 2-(trimethylsilylmethyl)propenoate
Formula : C9H18O2Si
Molecular Weight : 186,32 g/mol
Component Concentration
Ethyl 2-(trimethylsilylmethyl)acrylate
CAS-No. 74976-84-4 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides, silicon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: 2 - 8 °C
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: clear, liquid
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 70 - 72 °C at 13 hPa - lit.
boiling range
g) Flash point 61 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,897 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(三甲基甲硅烷甲基)丙烯酸乙酯 在 lithium aluminium deuteride 作用下， 生成 2-methylene-3-(trimethylsilyl)-1,1-dideuteriopropan-1-ol
  参考文献：
  名称：

  Nature of a trimethylenemethane-palladium complex

  摘要：

  DOI：

  10.1021/ja00540a041
• 作为产物：
  描述：

  ethyl 2-(hydroxymethyl)-3-(trimethylsilyl)propionate 在 diazabicyclo<5.4.0>undec-6-ene 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 13.0h， 生成 2-(三甲基甲硅烷甲基)丙烯酸乙酯
  参考文献：
  名称：

  Palladium-mediated cycloaddition approach to cyclopentanoids. Mechanistic studies

  摘要：

  DOI：

  10.1021/ja00346a036

文献信息

• Visible-Light-Mediated Metal-Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si−H Activation
  作者：Rong Zhou、Yi Yiing Goh、Haiwang Liu、Hairong Tao、Lihua Li、Jie Wu

  DOI：10.1002/anie.201711250

  日期：2017.12.22

  Although there has been significant progress in the development of transition‐metal‐catalyzed hydrosilylations of alkenes over the past several decades, metal‐free hydrosilylation is still rare and highly desirable. Herein, we report a convenient visible‐light‐driven metal‐free hydrosilylation of both electron‐deficient and electron‐rich alkenes that proceeds through selective hydrogen atom transfer

  尽管在过去的几十年中，烯烃在过渡金属催化的氢化硅烷化的开发方面已取得了重大进展，但无金属的氢化硅烷化仍然十分罕见，因此非常值得期待。在此，我们报道了通过缺氧和富电子烯烃的便捷的可见光驱动的无金属氢化硅烷化反应，该过程通过选择性氢原子转移进行Si​​-H活化而进行。有机光氧化还原催化剂4CzIPN与奎宁环烯-3-乙酸基酯的协同结合能够通过选择性Si-H活化实现缺电子烯烃的氢化硅烷化，而富电子烯烃的氢化硅烷化则是通过合并光氧化还原和极性反转催化来实现的。
• Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions
  作者：Akihiro Kobayashi、Tsubasa Matsuzawa、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1039/d0cc02253e

  日期：——

  A facile synthetic method for the preparation of allyl sulfoxides by S-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates, S-alkynylation and S-arylation were also accomplished.

  一种通过亚磺酸酯的S-烯丙基化制备烯丙基亚砜的简便合成方法，是通过sulf中间体进行的，而没有[3,3]-σ重排和所得烯丙基亚砜的进一步Pummerer型反应。在涉及involving盐中间体的合理反应机理的基础上，还完成了S-炔基化和S-芳基化。
• One-Pot, Three-Component Synthesis of Open-Chain, Polyfunctional Sulfones
  作者：Pierre Vogel、Laure Bouchez

  DOI：10.1055/s-2002-19797

  日期：——

  Silyl enol ethers of esters, ketones, as well as allylstannane and allylsilanes react with sulfur dioxide activated with t-BuMe2SiOSO2CF3 to give silyl sulfinates that can be reacted in the same pot with a variety of electrophiles generating the corresponding polyfunctional sulfones. The silyl sulfinate intermediates are formed via ene-reactions following probably concerted mechanisms.

  酯、酮的硅烯醇醚，以及烯丙基锡和烯丙基硅烷在用t-BuMe2SiOSO2CF3活化的二氧化硫作用下反应生成硅烷亚砜盐，这些亚砜盐可以与多种电亲体在同一反应锅中反应，生成相应的多功能磺烷。硅烷亚砜盐中间体通过ene反应形成，可能遵循协同机制。
• Bismuth Triflate-Catalyzed Addition of Allylsilanes to N-Alkoxycarbonylamino Sulfones: Convenient Access to 3-Cbz-Protected Cyclohexenylamines
  作者：Thierry Ollevier、Zhiya Li

  DOI：10.1002/adsc.200900710

  日期：2009.12

  Bismuth triflate was found to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. The reaction proceeded smoothly with a low catalyst loading of Bi(OTf)3⋅4 H2O (2–5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%). A sequential allylation reaction followed by ring-closing metathesis delivers 6–8

  发现三氟甲磺酸铋是烯丙基三甲基硅烷与N-烷氧基羰基氨基砜的Sakurai反应的有效催化剂。该反应的Bi的低催化剂载量（OTF）顺利进行3 ⋅4ħ 2 O（2-5摩尔％），得到相应的保护的高烯丙基胺在非常好的产率（最高至96％）。顺序的烯丙基化反应，然后进行闭环复分解，得到6-8元3-Cbz保护的环烯基胺。
• Direct and enantioselective α-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis
  作者：Anthony Mastracchio、Alexander A. Warkentin、Abbas M. Walji、David W. C. MacMillan

  DOI：10.1073/pnas.1002845107

  日期：2010.11.30

  The first enantioselective organocatalytic α-allylation of cyclic ketones has been accomplished via singly occupied molecular orbital catalysis. Geometrically constrained radical cations, forged from the one-electron oxidation of transiently generated enamines, readily undergo allylic alkylation with a variety of commercially available allyl silanes. A reasonable latitude in both the ketone and allyl silane components is readily accommodated in this new transformation. Moreover, three new oxidatively stable imidazolidinone catalysts have been developed that allow cyclic ketones to successfully participate in this transformation. The new catalyst platform has also been exploited in the first catalytic enantioselective α-enolation and α-carbooxidation of ketones.

  通过单占据分子轨道催化，已经实现了环状酮的第一个对映选择性有机催化α-烯丙基化反应。由暂时生成的烯胺一电子氧化而形成的几何约束的自由基阳离子，能够与多种商业可获得的烯丙基硅烷发生烯丙基烷基化反应。在这种新的转化中，环状酮和烯丙基硅烷组分都有相当大的宽容度。此外，已经开发了三种新的氧化稳定的咪唑啉酮催化剂，使环状酮能够成功参与这一转化。这种新的催化剂平台还被用于酮的首个催化对映选择性α-烯酰基化和α-碳氧化反应。