三氟甲烷磺酸4-甲基-2-(三甲基硅基)苯酯 | 262373-15-9

• 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4-甲基-2-(三甲基硅基)苯酯
• 中文别名: 4-甲基-2-(三甲基硅烷基)苯基三氟甲磺酸；三氟甲烷磺酸-4-甲基-2-(三甲基硅基)苯酯；2-(三甲基硅)-对甲苯基三氟甲基
• 英文名称: 4-methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate
• 英文别名: 4-methyl-2-(trimethylsilyl)phenyl triflate；(4-methyl-2-trimethylsilylphenyl) trifluoromethanesulfonate
• CAS: 262373-15-9
• 化学式: C₁₁H₁₅F₃O₃SSi
• 分子量: 312.385
• InChiKey: SKLVYEYSGSTOFD-UHFFFAOYSA-N

物化性质

• 沸点：
  300.8±42.0 °C(Predicted)
• 密度：
  1.22

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
• 安全说明：
  S24/25
• 海关编码：
  29319090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P234,P260,P264,P280,P301+P330+P331+P310,P303+P361+P353+P310+P363,P304+P340+P310,P305+P351+P338+P310,P390,P405,P406,P501
• 危险品运输编号：
  3265
• 危险性描述：
  H290,H314
• 储存条件：
  存放于惰性气体中，避免接触空气。

SDS

4-Methyl-2-(trimethylsilyl)phenyl Revision number: 5
Trifluoromethanesulfonate
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Methyl-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate

Revision number: 5

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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.
4-Methyl-2-(trimethylsilyl)phenyl
Trifluoromethanesulfonate

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Methyl-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate
Percent: >98.0%(GC)
CAS Number: 262373-15-9
Synonyms: 4-Methyl-2-(trimethylsilyl)phenyl Triflate , Trifluoromethanesulfonic Acid 4-Methyl-2-
(trimethylsilyl)phenyl Ester , 2-(Trimethylsilyl)-p-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.
4-Methyl-2-(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: 1.22
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:
4-Methyl-2-(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4-甲基-2-(三甲基硅基)苯酯 在 sodium azide 、 18-冠醚-6 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以51%的产率得到5-甲基苯并三氮唑
  参考文献：
  名称：

  通过[3 + 2]叠氮化钠与芳烃的环化反应选择性合成NH和N-芳基苯并三唑。

  摘要：

  已证明NaN3在[3 + 2]环合中作为叠氮化物组分的合成效用，该芳烃由2-（三甲基甲硅烷基）芳基三氟甲磺酸产生的芳烃导致无过渡金属合成NH和N-芳基苯并三唑。使用CsF作为CH3CN中的氟化物源，可以高选择性地生成NH苯并三唑，而不是预期的叠氮苯。有趣的是，在开瓶反应中使用KF和THF作为溶剂形成N-芳基苯并三唑。此外，还提出了苯并三唑的N1-芳基化的方法。

  DOI：

  10.1021/acs.joc.9b02198
• 作为产物：
  描述：

  2-溴-4-甲基苯酚 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 三氟甲烷磺酸4-甲基-2-(三甲基硅基)苯酯
  参考文献：
  名称：

  三氟甲基芳基磺酸盐（TFMS）：适用的三氟甲氧基化试剂

  摘要：

  氮之后，氟可能是掺入小分子中的另一个最受欢迎的杂原子。在许多含氟基团中，三氟甲基芳基醚（ArOCF 3）在药物设计中具有独特的特性，难以合成，因此开发了许多不同的方法来制备它们。的一种新的一锅法合成ø -碘-芳基三氟甲基醚（ArOCF 3 I）用的反应描述trifluoromethoxylation和碘化与三氟甲基芳基磺酸盐（TFMS）在该手稿。通过筛选不同的溶剂，冠醚，底物来优化反应条件，并且产物的比例和收率处于中等至高收率（高达86％）。

  DOI：

  10.1016/j.tetlet.2019.04.033

文献信息

• Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
  作者：Ting-Yu Zhang、Chang Liu、Chao Chen、Jian-Xin Liu、Heng-Ye Xiang、Wei Jiang、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.7b03580

  日期：2018.1.5

  An efficient and environmentally benign Cu-mediated method was developed for direct cascade C–H/N–H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C–H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline

  开发了一种高效且环境友好的铜介导的方法，用于直接级联C–H / N–H环化，以构建多杂环吲哚并喹啉支架。该方法突出了在有机合成中将惰性C–H键转变为通用官能团的新兴策略，并为有效合成吲哚[3,2- c ]和[2,3- c ]喹啉生物碱提供了新的通用方法。
• Palladium-Catalyzed Controlled Carbopalladation of Benzyne
  作者：Eiji Yoshikawa、K. V. Radhakrishnan、Yoshinori Yamamoto

  DOI：10.1021/ja001205a

  日期：2000.8.1

  derivatives 16 in moderate yields (ii). The reaction of benzyne precursor 1a with the alkynes 15a−c,f−h in the presence of Pd(OAc)2 (5 mol %)−(o-tolyl)3P (5 mol %) catalyst and CsF (2.0 equiv) in CH3CN gave the phenanthrene derivatives 17 (iii), whereas the reaction of 1a with the alkynes 15a,b,i in the presence of the same catalysts and CsF in CH3CN−toluene gave the indene derivatives 18 in good yields (iv)

  2-三甲基甲硅烷基苯基三氟甲磺酸盐 1a，一种苄基前体，在 CsF（2.0 当量）和 Pd2(dba)3·CHCl3 (2.5 mol %)-dppf (5 mol %) 存在下与烯丙基氯化物 2a-f 反应:1 CH3CN 和 THF 的混合溶剂以良好的产率 (i) 产生菲衍生物 3 及其次要的区域异构体 4，并且 1a 与 2a 和内部炔烃 15a,ce 的反应以中等产率提供萘衍生物 16 （二）。在 Pd(OAc)2 (5 mol %)-(o-tolyl)3P (5 mol %) 催化剂和 CsF (2.0 equiv) 存在下，苄基前体 1a 与炔烃 15a-c,f-h 的反应CH3CN 得到菲衍生物 17 (iii)，而 1a 与炔烃 15a,b,i 在相同催化剂和 CsF 存在下在 CH3CN-甲苯中的反应以良好的产率 (iv) 得到茚衍生物 18。
• Stereoselective [3+2] cycloaddition of N-tert-butanesulfinyl imines to arynes facilitated by a removable PhSO₂CF₂ group: synthesis and transformation of cyclic sulfoximines
  作者：Wenchao Ye、Laijun Zhang、Chuanfa Ni、Jian Rong、Jinbo Hu

  DOI：10.1039/c4cc05042h

  日期：——

  unprecedented [3+2] cycloaddition between N-tert-butanesulfinyl imines and arynes provides a stereoselective method for the synthesis of cyclic sulfoximines. Not only does the difluoro(phenylsulfonyl)methyl group play an important role in facilitating the cycloaddition reaction, it can also be removed or substituted through the transformation of the difluorinated cyclic sulfoximines to cyclic sulfinamides

  N-叔丁烷亚磺酰基亚胺和芳烃之间空前的[3 + 2]环加成反应为合成环亚砜亚胺提供了立体选择方法。二氟（苯磺酰基）甲基不仅在促进环加成反应中起重要作用，还可以通过将二氟化环亚砜亚胺转化为环亚磺酰胺而被除去或取代。
• Three-Component Aminoselenation of Arynes
  作者：Rahul N. Gaykar、Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1021/acs.orglett.9b03789

  日期：2019.12.6

  The three-component coupling of tertiary amines, arynes, and aryl selenium bromide or diaryl diselenide as an electrophilic selenium source allowing the synthesis of 2-selanyl aniline derivatives is reported. This aminoselenation reaction of arynes installs a C-N and C-Se bond under mild conditions, and the products are formed in moderate to good yields. This reaction is compatible with various functional

  据报道，叔胺，芳烃和芳基溴化溴化物或二芳基二硒化物作为亲电子硒源的三组分偶联可以合成2-硒代苯胺衍生物。芳烃的这种氨基硒化反应在温和的条件下安装了CN和C-Se键，并且产物的产率中等至良好。该反应与各种官能团相容，并且还提供了对反应机理的初步研究。
• 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。