2-三甲基甲硅烷基乙基苯基砜 | 73476-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-三甲基甲硅烷基乙基苯基砜
• 英文名称: 1-benzenesulfonyl-2-trimethylsilylethane
• 英文别名: 1-phenylsulfonyl-2-trimethylsilylethane；phenyl 2-trimethylsilylethyl sulfone；Trimethyl(2-(phenylsulfonyl)ethyl)silane；2-(benzenesulfonyl)ethyl-trimethylsilane
• CAS: 73476-18-3
• 化学式: C₁₁H₁₈O₂SSi
• mdl: MFCD00015929
• 分子量: 242.414
• InChiKey: IVPQHMQOYMNETK-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52 °C(lit.)
• 沸点：
  347.4±34.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)
• 闪点：
  >230 °F
• 溶解度：
  sol all common ethereal, halocarbon, and hydrocarbon solvents.

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 安全说明：
  S22,S24/25

SDS

Name:	Phenyl 2-(trimethylsilyl)ethyl sulfone 99+% Material Safety Data Sheet
Synonym:	1-(Phenylsulfonyl)-2-(trimethylsilyl)ethan
CAS:	73476-18-3

Section 1 - Chemical Product MSDS Name:Phenyl 2-(trimethylsilyl)ethyl sulfone 99+% Material Safety Data Sheet
Synonym:1-(Phenylsulfonyl)-2-(trimethylsilyl)ethan

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73476-18-3	Phenyl 2-(trimethylsilyl)ethyl sulfone	99+	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: 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. 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 immediately.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 73476-18-3: United Kingdom, WEL - TWA: (listed as silica, amorphous): 6 mg/m3 (inhalable dust); 2.4 mg/m3 TWA (respirable dust) United Kingdom, WEL - STEL: (listed as silica, amorphous): 18 mg/ STEL (inhalable dust); 7.2 mg/m3 STEL (respirable dust) Russia: (listed as silica, amorphous): 1 mg/m3 TWA 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 50.00 - 53.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: 109 deg C ( 228.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in diethylether
Specific Gravity/Density:
Molecular Formula: C11H18O2SSi
Molecular Weight: 242.41

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, silicon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73476-18-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phenyl 2-(trimethylsilyl)ethyl sulfone - 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
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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 73476-18-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73476-18-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73476-18-3 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：

  2-三甲基甲硅烷基乙基苯基砜 在 chromium(VI) oxide 、 氢氧化钾 、 sodium hypochlorite 、 正丁基锂 、 硫酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 4.17h， 生成 2-(Benzenesulfonyl)-3-phenyl-1-propen-3-ol
  参考文献：
  名称：

  1-Benzenesulfonyl-2-trimethylsilylethane and 1-benzenesulfonyl-1-chloro-2-trimethylsilylethane; efficient reagents for sulfonyl--vinylation

  摘要：

  DOI：

  10.1016/s0040-4039(00)87640-6
• 作为产物：
  描述：

  乙烯基三甲基硅烷 在 bis(1,5-cyclooctadiene)nickel (0) 、 溶剂黄146 、 三乙胺 、 copper dichloride 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 58.0h， 生成 2-三甲基甲硅烷基乙基苯基砜
  参考文献：
  名称：

  有机合成中的砜试剂：VI。磺酰基和甲硅烷基取代的烃类在有机合成中作为通用的碳负离子前体

  摘要：

  已经研究了β-甲硅烷基取代的炔属，乙烯基和烷基砜的基本有机金属化学，并着重于金属化，碳金属化和碳-碳不饱和键的化学还原。对2-三甲基甲硅烷基乙烯基和2-三甲基甲硅烷基烷基砜进行了平滑和立体选择性锂化，碳原子α上的RLi形成磺酰基。用RMgX或LiCuR 2可以实现乙烯基砜的金属羰基化，但是仅使用LiCuR 2可以使羰基砜顺利地金属羰基化; 这些乙炔通过RMgX或RLi进行烷基脱磺酰化。讨论了这些磺酰基-甲硅烷基-烃类金属衍生物的合成实用性，并阐明了它们在精制碳骨架中的价值，可用于制备烯烃，丙二烯，碳环化合物和立体定义的乙烯基砜。

  DOI：

  10.1016/0022-328x(85)87362-9

文献信息

• A general approach to iridoids by applying a new Julia olefination and a tandem anion-radical-carbocation crossover reaction
  作者：Lucie Řehová、Martin Dračínský、Ullrich Jahn

  DOI：10.1039/c6ob01599a

  日期：——

  A unified, asymmetric approach to the total synthesis of naturally occurring iridoids is presented. The synthesis features a recently discovered ortho → α transmetalation of alkyl aryl sulfone carbanions, thus enabling Julia reactions, by which so far hardly accessible disilylated olefins have been obtained. A subsequent tandem alkoxycarbonylation/oxidative radical cyclization afforded substituted

  提出了一种统一的，不对称的方法来自然合成虹彩化合物。该合成具有最近发现的烷基芳基砜碳负离子的邻位→α过渡金属化的特征，从而实现了朱莉娅反应，到目前为止，通过这种反应很难获得二甲苯化的烯烃。随后的串联烷氧基羰基化/氧化自由基环化得到具有高非对映选择性的取代的环戊烷结构单元。这些化合物作为独特的中心中间体，可短时间获得二氢荆芥内酯，二氢内酯和其他潜在的虹彩化合物。
• Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation
  作者：Laura Iannazzo、Gary A. Molander

  DOI：10.1002/ejoc.201200767

  日期：2012.9

  silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poorly electrophilic acceptors such as phenylvinyl sulfone by cleavage of the Si-Si bond of a disilane reagent. The scope of this reaction was extended to various electrophiles bearing different electron-withdrawing groups and afforded the

  通过铜（I）催化的α，β-不饱和化合物的共轭硅烷化制备了几种烷基和乙烯基硅烷。首先研究了最佳反应条件，以通过乙硅烷试剂的 Si-Si 键断裂实现亲核硅物质与弱亲电子受体（如苯基乙烯基砜）的共轭加成。该反应的范围扩展到各种带有不同吸电子基团的亲电子试剂，并提供所需的取代烷基和乙烯基硅烷。在广泛的市售乙硅烷中，还研究了烷基-、芳基-和乙氧基乙硅烷的反应性。
• Enantioselective synthesis of the methylenecyclopropane derivative related to hypoglycine, from malic acid
  作者：Barbara Achmatowicz、Marek M. Kabat、Janusz Krajewski、Jerzy Wicha

  DOI：10.1016/s0040-4020(01)89048-7

  日期：——

  Synthesis of (S)-methylenecyclopropaneacetic acid starting from L-(−)-malic acid, via (2S)-O-tert-butyldimethylsilyl-1,2-epoxybutan-4-ol and 1-O-tert-butyldiphenylsilyl-5-benzenesulfonyl-6-trimethylsilylhexane-1,3-diols as the key intermediates, is described.

  由L-（-）-苹果酸经（2S）-O-叔丁基二甲基甲硅烷基-1,2-环氧丁烷-4-醇和1-O-叔丁基二苯基甲硅烷基-5-苯甲酸合成（S）-亚甲基环丙烷乙酸描述了作为关键中间体的苯磺酰基-6-三甲基甲硅烷基己烷-1,3-二醇。
• Enantioselective synthesis of the methylenecyclopropane derivative related to hypoglycine, starting from malic acid
  作者：Marek M. Kabat、Jerzy Wicha

  DOI：10.1016/s0040-4039(00)79488-3

  日期：1991.1

  The methylenecyclopropane derivative was synthesized from (S) malic acid via epoxide and β-trimethylsilyl sulfone .

  由（S）苹果酸经环氧化物和β-三甲基甲硅烷基砜合成亚甲基环丙烷衍生物。
• Iterative syn-1,3,5-triol synthesis utilizing the reaction of β-(trimethylsily)dalkyl phenyl sulphones with oxiranes
  作者：Barbara Achmatowicz、Jerzy Wicha

  DOI：10.1016/s0957-4166(00)86085-1

  日期：1993.3

  Partly protected triols 8a and 8b were synthesised from epoxide 1 using β-trimethylsilyl sulphones 2a and 2a for the chain elongation and the Cardillo procedure for diastereoselective two-step epoxidation of homoallylic alcohols.

  使用β-三甲基甲硅烷基砜2a和2a从环氧化物1合成部分受保护的三醇8a和8b，用于链延长，以及Cardillo程序用于对映体选择性两步环氧化均丙醇。