三氟甲烷磺酸-2-甲基-6-(三甲基硅基)苯酯 | 556812-44-3

• 物质功能分类: 化学试剂 - 有机试剂 - 甲苯磺酸酯
• 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: 三氟甲烷磺酸-2-甲基-6-(三甲基硅基)苯酯
• 中文别名: 三氟甲烷磺酸2-甲基-6-(三甲基硅基)苯酯
• 英文名称: 2-methyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate
• 英文别名: 2-methyl-6-(trimethylsilyl)phenyl triflate；6-methyl-2-(trimethylsilyl)phenyl triflate；(2-methyl-6-trimethylsilylphenyl) trifluoromethanesulfonate
• CAS: 556812-44-3
• 化学式: C₁₁H₁₅F₃O₃SSi
• 分子量: 312.385
• InChiKey: ZCWWZFXNICWDIB-UHFFFAOYSA-N

物化性质

• 沸点：
  299.6±40.0 °C(Predicted)
• 密度：
  1.23

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  8
• 海关编码：
  29319090
• 危险品运输编号：
  UN 3265
• 储存条件：
  存放于惰性气体中，避免接触空气。

SDS

2-Methyl-6-(trimethylsilyl)phenyl
Trifluoromethanesulfonate
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2-Methyl-6-(trimethylsilyl)phenyl Trifluoromethanesulfonate

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 1
Corrosive to metals
HEALTH HAZARDS
Category 1B
Skin corrosion/irritation
Serious eye damage/eye irritation Category 1
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
May be corrosive to metals
Hazard statements
Causes severe skin burns and eye damage
Precautionary statements:
[Prevention] Keep only in original container.
Do not breathe dust/fume/gas/mist/vapours/spray.
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing.
IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
Wash contaminated clothing before reuse.
Immediately call a POISON CENTER or doctor/physician.
Absorb spillage to prevent material damage.
[Storage] Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.
2-Methyl-6-(trimethylsilyl)phenyl
Trifluoromethanesulfonate

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2-Methyl-6-(trimethylsilyl)phenyl Trifluoromethanesulfonate
Percent: >96.0%(GC)
CAS Number: 556812-44-3
Synonyms: 2-Methyl-6-(trimethylsilyl)phenyl Triflate , Trifluoromethanesulfonic Acid 2-Methyl-6-
(trimethylsilyl)phenyl Ester , 6-(Trimethylsilyl)-o-tolyl Trifluoromethanesulfonate
Chemical Formula: C11H15F3O3SSi

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Immediately call a POISON CENTER or doctor/physician.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Immediately call a POISON CENTER or doctor/physician.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing.Immediately call a POISON CENTER or
doctor/physician.
Ingestion: Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT
induce vomiting.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Unsuitable extinguishing Solid streams of water
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use extra personal protective equipment (self-contained breathing apparatus). Keep
protective equipment and people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-
emergency procedures: involved personnel should be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Wash hands and face thoroughly after
handling.
Use a closed system if possible. Use a ventilation, local exhaust if vapour or aerosol
will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Use corrosive resistant equipment.
2-Methyl-6-(trimethylsilyl)phenyl
Trifluoromethanesulfonate

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Section 7. HANDLING AND STORAGE
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Packaging material: Comply with laws. Keep only in original container.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust. Also install safety shower and eye bath.
Engineering controls:
Personal protective equipment
Respiratory protection: Half or full facepiece respirator, self-contained breathing apparatus(SCBA), supplied
air respirator, etc. Use respirators approved under appropriate government standards
and follow local and national regulations.
Hand protection: Impervious gloves.
Safety goggles. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Clear
Form:
Colour: Colorless - Slightly pale yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
No data available
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: 1.23
Solubility(ies):
[Water] No data available
No data available
[Other solvents]

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride, Sulfur oxides, Silicon oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:
2-Methyl-6-(trimethylsilyl)phenyl
Trifluoromethanesulfonate

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: 8: Corrosive.
UN-No: 3265
Proper shipping name: Corrosive liquid, acidic, organic, n.o.s.
Packing group: II

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸-2-甲基-6-(三甲基硅基)苯酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 palladium diacetate 、 potassium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 36.5h， 生成 4'-acetyl-3-methyl-5-(trimethylsilyl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  硼基（杂）芳烃前体作为通用的丙烯酸化试剂：通过C ？H活化和正交反应性

  摘要：

  （Pinacolato）硼基邻甲硅烷基（杂）芳基三氟甲磺酸酯是一类新型的芳基化砌块。它们通过在广泛的转化范围内化学选择性地传递硼酸酯或（杂）芳烃反应性而展示出独特的多功能性。这种方法可以实现氟化物活化的（杂）芳烃前体的前所未有的后功能化，例如作为过渡金属催化中的底物，并为芳基硼酸酯的后功能化提供了宝贵的新可能性，而无需使用专门的保护基。

  DOI：

  10.1002/anie.201503152
• 作为产物：
  描述：

  6-溴-2-甲基苯酚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 三氟甲烷磺酸-2-甲基-6-(三甲基硅基)苯酯
  参考文献：
  名称：

  N,N‐Diarysulfonamide reduces proinflammatory cytokine interleukin‐6 levels in cells through nuclear factor‐κB regulation

  摘要：

  The synthesized sulfonamides were evaluated for cytotoxicity followed by the cytokine/inflammatory marker’s inhibition capability and its mechanism of action in RAW‐264.7 cells. Elevated interleukin‐6 (IL‐6) levels have been reported in inflammatory conditions and inflammation‐associated disorders. Hence, reducing the IL‐6 levels in inflammatory conditions can serve as an attractive therapeutic target in dealing the inflammation. Among 42 compounds, seven compounds showed significant inhibition of IL‐6 levels in lipopolysaccharide (LPS) challenged RAW‐264.7 cells at 12.5 µM concentration. Further, investigation revealed that the IC50 value of these compounds for reducing IL‐6 levels was found to be in the range of 9.7 to 2.6 µM. The promising compounds 5y (IC50 of 2.6 µM) and 5n (IC50 of 4.1 µM) along with other derivatives fulfil drug‐likeness parameters laid down by Lipinski’s rule of five. Further, analysis using RTqPCR and Western‐blot analysis revealed that treatment with 5n significantly reduced the expression of pro‐inflammatory, inflammatory and macrophage marker’s expression (IL‐1β, CCL2, COX2 and CD68) compared to LPS control. The mechanistic evaluation showed that RL‐442 exhibited anti‐inflammatory properties by modulating the nuclear factor‐κB (NF‐κB) activation. The identified compound can be a promising candidate for further discovery efforts to generate a preclinical candidate effective in inflammation.

  DOI：

  10.1002/cmdc.202300598

文献信息

• 2,3-Diaroyl benzofurans from arynes: sequential synthesis of 2-aroyl benzofurans followed by benzoylation
  作者：Kashmiri Neog、Babulal Das、Pranjal Gogoi

  DOI：10.1039/c8ob00631h

  日期：——

  strategy for the direct synthesis of 2-aroyl benzofurans from aryne precursors has been developed. This reaction proceeds via C–O and C–C bond cleavage as well as C–O and C–C bond formation in a single reaction vessel. The methodology provides good yields of 2-aroyl benzofurans and tolerates a variety of functional groups. The synthesized 2-aroyl benzofurans were further benzoylated at 3-positions and

  已经开发了从芳烃前体直接合成2-芳酰基苯并呋喃的级联合成策略。该反应通过在单个反应容器中进行C–O和C–C键断裂以及C–O和C–C键形成而进行。该方法可提供2-芳酰基苯并呋喃的良好收率，并能耐受各种官能团。合成的2-芳酰基苯并呋喃在3-位进一步被苯甲酰化，并且合成的2，3-二酰酰基苯并呋喃结构之一通过X射线晶体学法得到明确证实。
• Facile Synthesis of Diverse Multisubstituted <i>ortho</i>-Silylaryl Triflates via C–H Borylation
  作者：Suguru Yoshida、Ken Shimomori、Takako Nonaka、Takamitsu Hosoya

  DOI：10.1246/cl.150535

  日期：2015.10.5

  Diverse multisubstituted ortho-silylaryl triflates were efficiently synthesized from simple ortho-silylaryl triflates via iridium-catalyzed regioselective C–H borylation and subsequent deborylative functionalizations. An azidoaryne precursor synthesized by this method served as a useful bis-reactive platform molecule, thus demonstrating the utility of the method for preparing diverse aromatic compounds.

  通过铱催化的区域选择性C-H硼化和随后的脱硼功能化，从简单的邻硅烷基芳基三氟甲磺酸酯高效合成了多取代的邻硅烷基芳基三氟甲磺酸酯。通过这种方法合成的叠氮芳炔前体是一种有用的双反应平台分子，从而证明了该方法在制备多种芳香化合物方面的实用性。
• Synthesis of aryl ethers of carbohydrates <i>via</i> reaction with arynes: selective <i>O</i>-arylation of <i>trans</i>-vicinal dihydroxyl groups in carbohydrates
  作者：Monika Bhardwaj、Nazar Hussain、Irshad Ahmad Zargar、Ashutosh K. Dash、Debaraj Mukherjee

  DOI：10.1039/d0ob00540a

  日期：——

  A new method for the O-arylation of carbohydrates under metal-free conditions using arynes as an aryl source has been developed. This approach works well with mono, di and trihydroxy compounds. Preferential O-arylation takes place at primary over secondary and equatorial over axial. Site-selective O-arylation was achieved with the substrate having trans vicinal diequatorial hydroxyls.

  已开发出一种新的方法，以芳烃为芳烃，在无金属条件下对碳水化合物进行O-芳基化。这种方法适用于单，二和三羟基化合物。优先O芳基化发生在初级，次级和赤道轴向。用具有反式邻位二甲基羟基的底物实现了位点选择性的O-芳基化。
• Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes
  作者：Yuanming Li、Christian Mück-Lichtenfeld、Armido Studer

  DOI：10.1002/anie.201608144

  日期：2016.11.7

  of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β‐elimination give rise to di‐, tri‐, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of

  原位生成的芳烃与乙烯基硫化物的反应可在（3 + 2）环加成反应中提供苯甲酰化sulf化烷基化ides。用亲电子试剂（质子转移或第二个芳烃加成）捕集中间亚烷基并随后进行β-消除反应会生成具有高立体选择性的二，三或四取代烯烃。实验研究和DFT计算可洞悉这些级联反应的机理。
• Three-Component Coupling of Arynes, Aminosilanes, and Aldehydes
  作者：Hiroto Yoshida、Takami Morishita、Hiroyuki Fukushima、Joji Ohshita、Atsutaka Kunai

  DOI：10.1021/ol071347a

  日期：2007.8.1

  A three-component coupling of arynes, aminosilanes, and aldehydes enables diverse amino and hydroxymethyl groups to be incorporated directly into 1,2-positions of aromatic rings.

  芳烃，氨基硅烷和醛的三组分偶联使得各种氨基和羟甲基可以直接引入芳香环的1,2-位。