2-碘苯基三氟甲磺酸酯 | 129112-26-1

• 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: 2-碘苯基三氟甲磺酸酯
• 中文别名: 2-碘苯三氟甲磺酸盐
• 英文名称: 2-iodophenyl trifluoromethanesulfonate
• 英文别名: 2-iodophenyl triflate；(2-iodophenyl) trifluoromethanesulfonate
• CAS: 129112-26-1
• 化学式: C₇H₄F₃IO₃S
• 分子量: 352.073
• InChiKey: AXIDYNSWXPNBLG-UHFFFAOYSA-N

物化性质

• 沸点：
  308℃
• 密度：
  2.035
• 闪点：
  140℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2906299090
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  室温且干燥

SDS

2-Iodophenyl Trifluoromethanesulfonate
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2-Iodophenyl Trifluoromethanesulfonate

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2-Iodophenyl Trifluoromethanesulfonate
Percent: >98.0%(GC)
CAS Number: 129112-26-1
Synonyms: Trifluoromethanesulfonic Acid 2-Iodophenyl Ester , 2-Iodophenyl Triflate
C7H4F3IO3S
Chemical Formula:

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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.
Get medical advice/attention if you feel unwell.
2-Iodophenyl Trifluoromethanesulfonate

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
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.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: 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 ventilation, local exhaust if vapour or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Comply with laws.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.
2-Iodophenyl Trifluoromethanesulfonate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Slightly pale yellow - Yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
1.94
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents] No data available

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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 Iodide, Hydrogen fluoride, Sulfur
products: oxides

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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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.
2-Iodophenyl Trifluoromethanesulfonate

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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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：

  2-碘苯基三氟甲磺酸酯 在 三氟化硼乙醚 、 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.92h， 生成 4-硝基苯酚三氟甲基磺酸酯
  参考文献：
  名称：

  Diaryliodonium盐的分子内芳基迁移：获得邻碘二芳基醚的途径

  摘要：

  通过使用邻位的三氟甲磺酸取代的二芳基碘鎓盐，开发了一种通过分子内芳基迁移合成邻碘二芳基醚的新方法。反应条件温和，底物范围广。机械学的见解表明了磺酰基定向的亲核芳族取代途径。另外，产物邻碘二芳基醚可作为通用合成子，已通过数个偶联反应得到证明。此外，通过这种芳基迁移步骤合成了3-碘-1-甲状腺素（3-T 1）衍生物的有用的甲状腺素类似物。

  DOI：

  10.1002/anie.201806405
• 作为产物：
  描述：

  2-(三甲基硅)苯基三氟甲烷磺酸盐 在 aluminum (III) chloride 、 1,3-二碘-5,5-二甲基海因 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到2-碘苯基三氟甲磺酸酯
  参考文献：
  名称：

  Facile Synthesis of Diverse o-Iodoaryl Triflates from o-Silylaryl Triflates by Aluminum-mediated Desilyliodination

  摘要：

  一种方便的方法被开发用于通过去硅烷钨化反应制备多样的o-碘苯三氟甲磺酸酯。将o-硅烷芳基三氟甲磺酸酯与1,3-二碘-5,5-二甲基氢氨酸（DIH）在氯化铝存在下处理，能够有效地生成相应的o-碘苯三氟甲磺酸酯，包括具有多个1-碘-2-（三氟甲氧基）芳基基团的化合物。通过铱催化的C–H硼化反应，利用易得的简单o-硅烷芳基三氟甲磺酸酯，随后进行去硼转化和后续去硅烷碘化反应，可以简单地制备出各种多取代的o-碘苯三氟甲磺酸酯。

  DOI：

  10.1246/cl.190223

文献信息

• <i>Ortho</i> -Trialkylstannyl Arylphosphanes by C-P and C-Sn Bond Formation in Arynes
  作者：Yuanming Li、Shyamal Chakrabarty、Christian Mück-Lichtenfeld、Armido Studer

  DOI：10.1002/anie.201509329

  日期：2016.1.11

  A novel and efficient approach to ortho‐trialkylstannyl arylphosphanes by the reaction of arynes generated in situ with stannylated phosphanes (R3SnPR2) is described. Concurrent CP and CSn bond formation occurs with high yields, and stannylated products are easily transformed into valuable ortho‐substituted arylphosphanes. The reaction features high efficiency, good regioselectivity, and excellent

  一种新颖和有效的方法来邻位由就地与stannylated膦生成arynes的反应-trialkylstannyl arylphosphanes（R 3 Sn的 PR 2）进行说明。并发Ç  P和C  Sn键的形成具有高的产率发生，并且stannylated产品很容易转化成有价值的邻位-取代的arylphosphanes。该反应具有高效率，良好的区域选择性和优异的实用性的特征。
• Ligand-Enabled Gold-Catalyzed C(sp²)–N Cross-Coupling Reactions of Aryl Iodides with Amines
  作者：Manjur O. Akram、Avishek Das、Indradweep Chakrabarty、Nitin T. Patil

  DOI：10.1021/acs.orglett.9b03082

  日期：2019.10.4

  example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong

  报道了芳基碘化物与胺的辅助（P，N）-配体使能的金催化的CN交叉偶联反应的第一个例子。在从头合成，后期修饰和级联过程中获得官能化的吲哚酮和咔唑的反应具有很高的通用性，这突出了所提出策略的合成潜力。用ESI-HRMS和NMR监测反应为原位形成假定的高价Au（III）中间体提供了有力的证据。
• Auto-Tandem Catalysis: Synthesis of Acridines by Pd-Catalyzed C=C Bond Formation and C(<i>sp²</i>)-N Cross-Coupling
  作者：Zhongxing Huang、Yang Yang、Qing Xiao、Yan Zhang、Jianbo Wang

  DOI：10.1002/ejoc.201201070

  日期：2012.10.10

  A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C–N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized

  通过连续的C=C双键形成和C-N交叉偶联实现了钯催化合成吖啶的简便方法。各种功能化的吖啶可以通过简单的操作从容易获得的邻二卤代苯和 N-甲苯磺酰腙中获得。这种一锅法在两个耦合伙伴方面具有广泛的范围，并为功能化吖啶衍生物提供了一种有效的途径，这些衍生物通常难以通过以前已知的方法合成。
• Rh^I-Catalyzed Benzo/[7+1] Cycloaddition of Cyclopropyl-Benzocyclobutenes and CO by Merging Thermal and Metal-Catalyzed CC Bond Cleavages
  作者：Xu-Fei Fu、Yu Xiang、Zhi-Xiang Yu

  DOI：10.1002/chem.201405712

  日期：2015.3.9

  A Rh‐catalyzed benzo/[7+1] cycloaddition of cyclopropyl‐benzocyclobutenes (CP‐BCBs) and CO to benzocyclooctenones has been developed. In this reaction, CP‐BCB acts as a benzo/7‐C synthon and the reaction involves two CC bond cleavages: a thermal electrocyclic ring‐opening of the four‐membered ring in CP‐BCB and a Rh‐catalyzed CC cleavage of the cyclopropane ring.

  已开发出Rh催化的环丙基-苯并环丁烯（CP-BCBs）和CO向苯并环辛烯酮的苯并/ [7 + 1]环加成反应。在该反应中，CP-BCB充当苯并/ 7-C合成子，该反应涉及两个CC键裂解：CP-BCB中四元环的热电环开环和Rh催化的C C环丙烷环的裂解。
• Acylalkylation of Arynes Generated from <i>o</i>-Iodoaryl Triflates with Hydrosilanes and Cesium Fluoride
  作者：Mai Minoshima、Keisuke Uchida、Yu Nakamura、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1021/acs.orglett.1c00279

  日期：2021.3.5

  An efficient method to generate aryne intermediates from o-iodoaryl triflates triggered by triethylsilane and cesium fluoride is disclosed. This method realized the acylalkylation of arynes using easily available o-iodoaryl triflate-type precursors, which was difficult when using conventional nucleophilic activators. A wide range of (hetero)arenes including various fused benzothiazoles were successfully

  公开了一种由三乙基硅烷和氟化铯引发的邻碘芳基三氟甲磺酸酯生成芳烃中间体的有效方法。该方法使用容易获得的邻碘代芳基三氟甲磺酸酯型前体实现了芳烃的酰基烷基化，这在使用常规亲核活化剂时是困难的。由于邻芳基三氟甲磺酸酯具有良好的可及性和芳烃中间体的发散转化性，因此成功地从邻碘芳基三氟甲磺酸酯中成功合成了各种杂芳烃，包括各种稠合的苯并噻唑。