2,6-二-叔-丁基-4-甲基吡喃洋三氟甲烷磺酸盐 | 59643-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2,6-二-叔-丁基-4-甲基吡喃洋三氟甲烷磺酸盐
• 中文别名: 2,6-二叔丁基-4-甲基吡喃鎓三氟甲烷磺酸盐；2,6-二叔丁基-4-甲基吡喃咩三氟甲烷磺酸盐
• 英文名称: 2,6-di-tert-butyl-4-methylpyrylium trifluoromethanesulfonate
• 英文别名: 2,6-ditert-butyl-4-methylpyrylium;trifluoromethanesulfonate
• CAS: 59643-43-5
• 化学式: CF₃O₃S*C₁₄H₂₃O
• 分子量: 356.406
• InChiKey: OTVABNVGYCQZFO-UHFFFAOYSA-M

物化性质

• 熔点：
  163°C (dec.)
• 稳定性/保质期：
  避免接触水和氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2932999099
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

SDS

2,6-Di-tert-butyl-4-methylpyrylium Revision number: 5
Trifluoromethanesulfonate
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate

Revision number: 5

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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
Warning
Signal word
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
2,6-Di-tert-butyl-4-methylpyrylium Trifluoromethanesulfonate
Components:
Percent: ....
59643-43-5
CAS Number:
Synonyms: 2,6-Di-tert-butyl-4-methylpyrylium Triflate
Chemical Formula: C15H23F3O4S

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Get medical advice/attention if you feel unwell.
2,6-Di-tert-butyl-4-methylpyrylium
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:
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 Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: 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 dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust 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.
Packaging material: Comply with laws.

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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: Dust 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.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Slightly pale reddish yellow
2,6-Di-tert-butyl-4-methylpyrylium
Trifluoromethanesulfonate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Odour: No data available
pH: No data available
Melting point/freezing point:172°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[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 fluoride, Sulfur oxides
products:

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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
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
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 dissolve or mix material
with a combustible solvent and 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: Does not correspond to the classification standard of the United Nations
Not listed
UN-No:
2,6-Di-tert-butyl-4-methylpyrylium
Trifluoromethanesulfonate

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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：

  2,6-二-叔-丁基-4-甲基吡喃洋三氟甲烷磺酸盐 以 溶剂黄146 为溶剂， 反应 2.08h， 生成 4,4'-(c-2,t-4-Diphenyl-r-1,t-3-cyclobutandiyl)bis(2,6-di-tert-butylpyrylium)-bis(trifluormethansulfonat)
  参考文献：
  名称：

  Hesse, Konrad; Huenig, Siegfried, Liebigs Annalen der Chemie, 1985, # 4, p. 715 - 739

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟甲磺酸 、 三甲基乙酰氯 以84%的产率得到2,6-二-叔-丁基-4-甲基吡喃洋三氟甲烷磺酸盐
  参考文献：
  名称：

  A convenient two-step synthesis of 2,6-di-tert-butyl-4-methylpyridine, a sterically hindered nonnucleophilic base

  摘要：

  DOI：

  10.1021/jo00880a027

文献信息

• Chalcogenopyrylium Dyes as Differential Modulators of Organic Anion Transport by Multidrug Resistance Protein 1 (MRP1), MRP2, and MRP4
  作者：Robert L. Myette、Gwenaëlle Conseil、Sean P. Ebert、Bryan Wetzel、Michael R. Detty、Susan P. C. Cole

  DOI：10.1124/dmd.112.050831

  日期：2013.6

  Multidrug resistance proteins (MRPs) mediate the ATP-dependent efflux of structurally diverse compounds, including anticancer drugs and physiologic organic anions. Five classes of chalcogenopyrylium dyes (CGPs) were examined for their ability to modulate transport of [3H]estradiol glucuronide (E217 β G; a prototypical MRP substrate) into MRP-enriched inside-out membrane vesicles. Additionally, some CGPs were tested in intact transfected cells using a calcein efflux assay. Sixteen of 34 CGPs inhibited MRP1-mediated E217 β G uptake by >50% (IC50 values: 0.7–7.6 µ M). Of 9 CGPs with IC50 values ≤2 µ M, two belonged to class I, two to class III, and five to class V. When tested in the intact cells, only 4 of 16 CGPs (at 10 µ M) inhibited MRP1-mediated calcein efflux by >50% (III-1, V-3, V-4, V-6), whereas a fifth (I-5) inhibited efflux by just 23%. These five CGPs also inhibited [3H]E217 β G uptake by MRP4. In contrast, their effects on MRP2 varied, with two (V-4, V-6) inhibiting E217 β G transport (IC50 values: 2.0 and 9.2 µ M) and two (V-3, III-1) stimulating transport (>2-fold), whereas CGP I-5 had no effect. Strikingly, although V-3 and V-4 had opposite effects on MRP2 activity, they are structurally identical except for their chalcogen atom (Se versus Te). This study is the first to identify class V CGPs, with their distinctive methine or trimethine linkage between two disubstituted pyrylium moieties, as a particularly potent class of MRP modulators, and to show that, within this core structure, differences in the electronegativity associated with a chalcogen atom can be the sole determinant of whether a compound will stimulate or inhibit MRP2.

  多药耐药蛋白（MRPs）介导结构多样化化合物（包括抗癌药物和生理有机阴离子）的ATP依赖性外排。研究了五类硫族吡啶染料（CGPs）对[3H]雌二醇葡萄糖苷（E217 β G；一种典型的MRP底物）进入富含MRP的内侧外翻膜囊泡的调节能力。此外，某些CGPs在完整的转染细胞中使用钙黄绿素外排测定进行了测试。在34种CGPs中，有16种抑制了MRP1介导的E217 β G摄取超过50%（IC50值：0.7–7.6 µM）。在9种IC50值≤2 µM的CGPs中，两个属于I类，两个属于III类，五个属于V类。在完整细胞测试中，仅有16种CGPs中的4种（在10 µM浓度下）抑制了MRP1介导的钙黄绿素外排超过50%（III-1, V-3, V-4, V-6），而第五种（I-5）仅抑制了23%。这五种CGPs还抑制了MRP4对[3H]E217 β G的摄取。相较之下，它们对MRP2的影响各不相同，其中两种（V-4, V-6）抑制了E217 β G的运输（IC50值：2.0和9.2 µM），两种（V-3, III-1）则刺激了运输（>2倍），而CGP I-5没有任何影响。值得注意的是，尽管V-3和V-4对MRP2活性的影响相反，但它们的结构除了硫族原子（Se与Te）外是完全相同的。本研究首次识别了V类CGPs，它们具有独特的亚甲基或三亚甲基连接两个双取代吡啶基团，作为特别有效的MRP调节剂，并表明在这一核心结构内，与硫族原子相关的电负性差异可以是决定化合物是刺激还是抑制MRP2的唯一因素。
• Aromatic/Proaromatic Donors in 2-Dicyanomethylenethiazole Merocyanines: From Neutral to Strongly Zwitterionic Nonlinear Optical Chromophores
  作者：Raquel Andreu、Elena Galán、Jesús Orduna、Belén Villacampa、Raquel Alicante、Juan T. López Navarrete、Juan Casado、Javier Garín

  DOI：10.1002/chem.201002158

  日期：2011.1.17

  whereas 4H‐pyran‐4‐ylidene‐ and 4‐pyridylidene‐containing compounds are zwitterionic and 1,3‐dithiol‐2‐ylidene derivatives are close to the cyanine limit, anilino‐derived merocyanines are essentially neutral. This very large range of intramolecular charge transfer (ICT) gives rise to efficient second‐order NLO chromophores with μβ values ranging from strongly negative to strongly positive. In particular

  制备了推挽式化合物，其中一个芳香族电子供体与一个2-二氰基亚甲基噻唑受体结合。与具有芳香族供体的模型化合物相比，它们的性能更佳。结合实验（X射线衍射，1 H NMR，IR，拉曼，UV / Vis，非线性光学（NLO）测量）和理论研究表明，结构和溶剂效应决定了这些花菁的基态极化：而4 H含吡喃-4-亚烷基和4-吡啶亚基的化合物为两性离子型，1,3-二硫醇-2-亚烷基衍生物接近花青的限度，苯胺衍生的花菁本质上是中性的。分子内电荷转移（ICT）的范围非常广，可产生高效的二阶NLO生色团μβ值的范围从强负到强正。尤其是，吡喃亚烷基衍生物不寻常，因为它们在加长π间隔物时显示出ICT程度的提高，而该特征在于它们显示出的非常大的负μβ值。将形式为喹啉的2-二氰基亚甲基噻唑部分与原芳香族供体连接起来似乎是优化两性离子NLO发色团的一种有前途的方法。
• “Donor–Two-Acceptor” Dye Design: A Distinct Gateway to NIR Fluorescence
  作者：Naama Karton-Lifshin、Lorenzo Albertazzi、Michael Bendikov、Phil S. Baran、Doron Shabat

  DOI：10.1021/ja308124q

  日期：2012.12.19

  The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes

  基于分子反应的化学或生物分析物的检测越来越依赖于荧光方法，并且需要更灵敏、更特异和更通用的荧光分子。我们设计了基于供体-双受体 π 电子系统的开启机制的长波长荧光探针，该系统可以进行内部电荷转移以形成具有更长 π 电子系统的新荧光染料。几个潜在的供体和多个受体分子被结合到探针模块结构中，以产生通用的染料化合物。这个新的染料库在近红外 (NIR) 区域具有荧光发射。计算研究很好地再现了观察到的实验趋势，并提出了导致供体-双受体活性形式的高荧光和从潜伏形式观察到的低荧光的因素。HeLa 细胞的共聚焦图像表明所选染料的溶酶体渗透途径。这些染料通过开启激活机制发射 NIR 荧光的能力使它们成为体内成像应用的有希望的候选探针。
• An expedient synthesis of N,N-dialkylamino-dihydroxanthene-pyrylium conjugated near-infrared fluorescent dyes
  作者：Anthony Romieu、Jean-Alexandre Richard

  DOI：10.1016/j.tetlet.2015.12.010

  日期：2016.1

  expedient synthesis of amino-(nor)dihydroxanthene-based fluorophores is reported, proceeding in two steps from commercially available salicylic aldehydes. The synthesis relies on the one-pot construction of the (nor)dihydroxanthene scaffolds through an oxa-Michael/retro-Michael/vinylogous aldol/dehydration cascade sequence. Further extension of the π-conjugated systems through a condensation reaction with

  据报道，从商业上可得的水杨醛分两步进行氨基（正）二氢氧杂蒽基荧光团的合成。合成依赖于通过氧杂-迈克尔/复古迈克尔/葡萄酒醛醇缩合/脱水级联序列的（去）二氢氧杂蒽骨架的一锅构建。通过与2,4,6-三取代的吡啶鎓盐的缩合反应进一步扩展π共轭体系，导致了一类新型的近红外（NIR）荧光染料，其在极性介质中的吸收/发射最大值在705范围内分别为–778和785–828 nm。
• Octupolar Merocyanine Dyes: A New Class of Nonlinear Optical Chromophores
  作者：Yevgen M. Poronik、Vincent Hugues、Mireille Blanchard-Desce、Daniel T. Gryko

  DOI：10.1002/chem.201200718

  日期：2012.7.23

  moieties allows tuning of the optical properties to approach the cyanine limit (i.e., polymethine state), thus resulting in a red‐shift of the low‐energy one‐photon‐absorption band as well as to the rise of an intense two‐photon‐absorption band in the NIR region. To the best of our knowledge, this is the first synthesis and TPA characterization of octupolar merocyanine chromophores with typical low‐bond‐length

  设计并合成了一组新的八极子花青生色团。这些化合物是由1,3,5-三甲酰基-2,4,6-三羟基苯与杂环亲核试剂反应制得的。八极染料仅以开放染料的形式形成。染料的单光子吸收光谱和双光子吸收光谱由两个谱带组成：双光子吸收谱中的长波长谱带（1000 nm以上有几百个GM）与强烈的长波长吸收性很好地匹配。位于线性光谱可见区域中的谱带。有趣的是，在较高的能量下，在NIR区域观察到了另外一个强度更大的TPA谱带，这对应于一个弱允许的单光子电子跃迁。改变外围的杂环部分允许调节光学性能以接近花菁极限（i。例如，聚次甲基状态），从而导致低能量单光子吸收带发生红移，并导致近红外区域中强烈的双光子吸收带上升。据我们所知，这是具有典型的低键长交替的八极部花青生色团的首次合成和TPA表征。