2-(二吡咯-2-基)甲基三甲苯 | 159152-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 2-(二吡咯-2-基)甲基三甲苯
• 中文别名: 2-(二吡咯-2-基)甲基均三甲苯
• 英文名称: 5-(mesityl)dipyrromethane
• 英文别名: meso-mesityldipyrromethane；5-(2,4,6-trimethylphenyl)dipyrromethane；2,2'-(mesitylmethylene)bis(1H-pyrrole)；mesityldipyrromethane；2,2’-(2,4,6-trimethylphenylmethylene)bispyrrol；2,2’-(2,4,6-trimethylphenylmethylene)dipyrrole；2,2'-(2,4,6-trimethylphenylmethylene)bispyrrol；(2,4,6-trimethylphenyl)dipyrromethane；mesityldipyrrol-2-yl-methane；2-[1H-pyrrol-2-yl-(2,4,6-trimethylphenyl)methyl]-1H-pyrrole
• CAS: 159152-14-4
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: LMSFUWKGADQXES-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  456.5±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Dipyrrol-2-yl)methylmesitylene
Synonyms: 5-Mesityldipyrromethane

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-(Dipyrrol-2-yl)methylmesitylene
CAS number: 159152-14-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C18H20N2
Molecular weight: 264.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(二吡咯-2-基)甲基三甲苯 在 叠氮磷酸二苯酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 盐酸 、 三氟乙酸 为溶剂， 生成 [5-(4-methoxycarbonylphenyl)-15-(4-aminophenyl)-10,20-bis(2,4,6-trimethylphenyl)porphyrin]
  参考文献：
  名称：

  卟啉氨基酸-双（卟啉）酰胺的酰胺偶联，氧化还原和光物理性质†

  摘要：

  新的反式-AB 2 ç内消旋取代的卟啉与氨基酯的内消旋-取代基可调谐吸电子功率（B =三甲苯基，4-C 6 H ^ 4女，4-C 6 H ^ 4 CF 3，C 6 ˚F 5）为制备为游离胺3a-3d，N-乙酰化衍生物Ac-3a-Ac-3d和相应的锌（II）配合物Zn-Ac-3a-Zn-Ac-3d。几个酰胺键联的双卟啉，每个电极的电子密度可调卟啉从通过缩合反应（该氨基前体卟啉得到的网站4A-4D（锌（）和单-和双II））配合物的Zn 2 22-4d和锌1 1Zn 2 2-4D制备。个别卟啉单元之间在双（卟啉）的电子交互4是通过电化学实验（CV，EPR），电子吸收光谱，稳态和时间分辨荧光光谱结合DFT /上抗磁中性双PCM计算（卟啉探测）4和在各自带电的混合价基团4 +/- +/-上。互动通过–C 6 H 4 –NHCO–C 6 H 4 –桥，氧化和还原的位置以及最低的激发单重态S 1通过各个卟啉上的取代基和金属化状态进行调节。

  DOI：

  10.1039/c3dt50711d
• 作为产物：
  描述：

  2-decylsulfanyl-5-[(5-decylsulfanyl-1H-pyrrol-2-yl)-(2,4,6-trimethylphenyl)methyl]-1H-pyrrole 在 镍 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以390 mg的产率得到2-(二吡咯-2-基)甲基三甲苯
  参考文献：
  名称：

  烷硫基单元作为双吡咯甲烷合成中的α-吡咯保护基

  摘要：

  卟啉前体的合成需要在吡咯的α-和α'-位置（分别为2-和5-）处连续引入取代基。用作临时掩蔽剂并且不会失活的α-吡咯取代基将极大地促进这种合成，特别是对于β-（3,4）-未取代的吡咯，但是迄今为止尚无可用。一系列α-RS基团（R = Me，Et，n在这方面已经研究了β-癸基，包括确定在吡咯的3-，4-和5-位上的取代动力学以及在二吡咯甲烷形成中的应用。通过2-硫氰基吡咯（由吡咯，硫氰酸铵和碘制备）和相应的格氏试剂RMgBr的反应，将RS基团容易地引入到吡咯α-位。每个2-烷硫基基团在3-或5-（vs 4-）位置上使吡咯环朝氘化。使用2：1的2-（RS）吡咯/苯甲醛与催化量的InCl 3进行二吡咯甲烷合成在室温下，没有任何溶剂。使用阮内镍或镍配合物通过加氢脱硫除去α-RS基团。使用α-RS保护的吡咯的这种化学计量合成与采用醛和25-100摩尔当量的吡咯的传统合成相反。通过使2-（正癸硫基）吡咯/醛/

  DOI：

  10.1021/jo051806q

文献信息

• Synthesis, characterization, and reactivity of oxoiron(IV) porphyrin π-cation radical complexes bearing cationic N-methyl-2-pyridinium group
  作者：Yuna Suzuki、Masahiko Hada、Hiroshi Fujii

  DOI：10.1016/j.jinorgbio.2021.111542

  日期：2021.10

  reactivity of metalloenzymes. Here, to investigate the effect of the cationic charge near the heme in heme proteins, we synthesized new iron porphyrin complexes (1 and 2) having cationic 3-methyl-N-methyl-2-pyrdinium group and N-methyl-2-pyridinium group at one of the four meso-positions, respectively. The N-methyl-2-pyridinium groups could be introduced by Stille coupling used palladium catalysts. Oxoiron(IV)

  活性位点附近的电子电荷是控制金属酶反应性的重要因素。在这里，为了研究血红素蛋白中靠近血红素的阳离子电荷的影响，我们合成了具有阳离子 3-甲基-N-甲基-2-吡啶鎓和N-甲基-2-吡啶鎓的新型铁卟啉配合物（ 1和2 ）。分别在四个中间位置之一分组。N-甲基-2-吡啶鎓基团可以通过Stille偶联使用的钯催化剂引入。1 ( 1-CompI ) 和2 ( 2-CompI )的氧代铁 (IV) 卟啉π-阳离子自由基配合物 (Compound I)) 可溶于大多数有机溶剂，从而可以在相同条件下直接比较它们的电子结构和与四苯甲基卟啉 ( 3-CompI ) 和四-(2,6-二氯苯基)卟啉 ( 4-CompI ) 的化合物 I 的反应性。1-CompI的光谱数据与3 -CompI 的光谱数据接近，但1-CompI的氧化还原电位与4-CompI的接近。环氧化反应的动力学分析表明，1-CompI和2-Com
• Design and Photophysical Properties of Zinc(II) Porphyrin-Containing Dendrons Linked to a Central Artificial Special Pair
  作者：Frédérique Brégier、Shawkat M. Aly、Claude P. Gros、Jean-Michel Barbe、Yoann Rousselin、Pierre D. Harvey

  DOI：10.1002/chem.201101832

  日期：2011.12.16

  act as singlet and triplet energy acceptors or donors, depending on the dendrimeric systems. The presence of the paramagnetic d9 copper(II) in the dendrimers promotes singlet–triplet energy transfer from the zinc(II) tetra‐meso‐arylporphyrin to the bis(copper(II) porphyrin) unit and slow triplet–triplet energy transfer from the central bis(copper(II) porphyrin) fragment to the peripheral zinc(II)

  点击化学的合成和光物理性质，特别是一系列人造特殊对-树枝状体系（树枝状= G1，G2，G3；G x =锌（II））的中心核与周围发色团之间的光诱导能量和电子转移据报道，在二甲基黄嘌呤双（金属（II）卟啉）（金属=锌，铜）的中心核上构建了含四-内消旋-芳基卟啉的聚酰亚胺）。根据树状体系，树状体充当单线态和三线态能量受体或供体。顺磁性d的存在9铜（II）在树枝状聚合物促进了从锌（II）四-单线态-三线态能量传递的内消旋-芳基卟啉转移到双（铜（II）卟啉）单元，并且三重态-三重态能量从中心双（铜（II）卟啉）片段转移到周围的锌（II）四内消旋-芳基卟啉。如果以bis（锌（II）卟啉）为中心核，则观察到链折叠的证据；异双金属系统中三重态-三重态能量传递的存在清楚地证明了这一点，该过程只能在短距离内发生。
• Modulation of the Singlet−Singlet Through-Space Energy Transfer Rates in Cofacial Bisporphyrin and Porphyrin−Corrole Dyads
  作者：Claude P. Gros、Frédéric Brisach、Anastasia Meristoudi、Enrique Espinosa、Roger Guilard、Pierre D. Harvey

  DOI：10.1021/ic0613558

  日期：2007.1.1

  A new series of relatively flexible cofacial donor-acceptor dyads for singlet-singlet energy transfer with the corrole or etio-porphyrin free base and zinc porphyrin as the acceptor and donor, respectively, were synthesized and characterized (represented as (PMes2COx)ZnH3 (13), (PMes2CO)ZnH3 (14), and (PMes2CX)ZnH3 (15)) where (PMes2COx = [2-[5-(5,15-dimesitylcorrol-10-yl)-diphenylether-2'-yl]-13,17-diethyl-2

  18-四甲基卟啉基）]二苯醚）作为比较标准。通过测量荧光寿命得出的能量转移速率（kET）与最近报道的刚性固定的面对面二元组（（DPB）ZnH2（1），（DPX）ZnH2（ 2），（DPA）ZnH2（3），（DPO）ZnH2（4）和（DPS）ZnH2（5），其中（DPB = 1,8-双[5-（2,8,13,17-四乙基- 3,7,12,18-四甲基卟啉基）]联苯撑），（DPX = 4,5-双[5-（2,8,13,17-四乙基-3,7,12,18-四甲基卟啉基）]-9， 9-二甲基氧杂蒽），（DPA = 1,8-双[5-（2,8,13,17-四乙基-3,7,12,18-四甲基卟啉基）]蒽），（DPO = 4,6-bis [5-（2,8,13,17-四乙基-3,7,12,18-四甲基卟啉基）]二苯并呋喃）和（DPS = 4,6-双[5-（2,8,13,17-四乙基-3,7,12,18-四甲基卟啉
• Tautomerism and Atropisomerism in Free-Base (<i>meso</i>)-Strapped Porphyrins: Static and Dynamic Aspects
  作者：Maxence Urbani、Tomás Torres

  DOI：10.1002/chem.201403881

  日期：2014.12.1

  We report herein some outstanding examples of atropisomerism and tautomerism in five (meso‐)strapped porphyrins. Porphyrins S0–S4 have been synthesised, characterised and studied in detail by spectroscopic and spectrometric techniques, and their isomeric purity verified by HPLC analysis. In particular, they exhibit perfectly well‐defined NMR spectra that display distinct patterns depending on their

  我们在此报告了五个（内消旋）卟啉中阻转异构和互变异构的一些杰出实例。卟啉S0 – S4已通过光谱和光谱技术进行了合成，表征和详细研究，其异构体纯度已通过HPLC分析验证。特别是，它们表现出非常良好定义的NMR谱显示该不同的模式依赖于在室温下它们的平均对称性：Ç 2 v，d 2 d，c ^ 2 ħ，Ç 2 v，和d 2 ħ为S0 -分别为S4。NH互变异构现象是通过在[D 2 ]二氯甲烷中于S0（Δ = 48±1 kJ mol -1）和S1（Δ = 55±3 kJ mol -1）上进行的低温1 H NMR实验证明的。使人们了解了在室温下观察到的五种卟啉的平均光谱。另一方面，S2和S3在室温下是稳定的阻转异构体，由于其高的旋转势垒能而限制了它们带状桥的旋转，因此易于分离和表征。加热至82°C后，它们逐渐平衡至热力学比为64:36，有利于更稳定的S2异构体。通过1 H NMR光谱证实了该阻转异构
• Synthesis and Physicochemical Characterization ofmeso-Functionalized Corroles: Precursors of Organic-Inorganic Hybrid Materials
  作者：Jean-Michel Barbe、Gabriel Canard、Stéphane Brandès、Roger Guilard

  DOI：10.1002/ejoc.200500374

  日期：2005.11

  Cobalt(III) corroles exhibit an infinite selectivity for the coordination of carbon monoxide towards dioxygen and dinitrogen. This peculiar property thus allows their use as sensing devices for CO detection. Here are described the syntheses and physico-chemical characterization of meso mono-, bis- and tris(triethoxysilyl)-functionalized corroles, precursors of organic–inorganic materials. The corrole

  钴 (III) 钴对一氧化碳与分子氧和双氮的配位表现出无限的选择性。因此，这种特殊的特性允许它们用作检测 CO 的传感装置。这里描述了内消旋单-、双-和三（三乙氧基甲硅烷基）-官能化的可罗尔（有机-无机材料的前体）的合成和物理化学表征。在每种情况下都使用“2+1”方法实现了克罗环的形成，该方法包括在催化量的三氟乙酸存在下使两当量的二吡咯甲烷与一当量的芳族醛反应。三乙氧基甲硅烷基链对可咯尔的官能化是通过异氰酸酯的缩合反应进行的，在氨基或羟基上带有三乙氧基甲硅烷基末端。每个最终化合物和中间体都通过各种物理化学技术进行表征，例如 1H NMR、UV/Vis、MALDI/TOF 或 EI 质谱和元素分析。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)