2,2'-二吡咯基甲烷 | 21211-65-4

• 物质功能分类: 有机原料 - 含氮基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,2'-二吡咯基甲烷
• 中文别名: 2,2’-二吡咯基甲烷
• 英文名称: di(pyrrol-2-yl)methane
• 英文别名: dipyrromethane；di(1H-pyrrol-2-yl)methane；dipyrrylmethane；dipyrrolemethane；2,2'-dipyrrolylmethane；2,2’-dipyrrolylmethane；2,2′-dipyrrolylmethane；2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole
• CAS: 21211-65-4
• 化学式: C₉H₁₀N₂
• mdl: MFCD03931560
• 分子量: 146.192
• InChiKey: PBTPREHATAFBEN-UHFFFAOYSA-N

物化性质

• 熔点：
  72.0 to 77.0 °C
• 沸点：
  120°C/2mmHg(lit.)
• 密度：
  1.0976 (rough estimate)
• 溶解度：
  可溶于氯仿、甲醇
• 最大波长(λmax)：
  449nm(CHCl3)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 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
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  存储条件为0-10°C，需置于惰性气体中，并避免光照、与空气接触及加热。

SDS

2,2'-Dipyrrolylmethane Revision number: 6
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2,2'-Dipyrrolylmethane

Revision number: 6

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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: 2,2'-Dipyrrolylmethane
Percent: >97.0%(GC)
CAS Number: 21211-65-4
Chemical Formula: C9H10N2

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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.
2,2'-Dipyrrolylmethane

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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 refrigerator.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive, Light-sensitive, Air-sensitive
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:
2,2'-Dipyrrolylmethane

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Colour: White - Pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:74°C
Boiling point/range: 120°C/0.3kPa
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]
Soluble: Methanol
Log Pow: 1.77

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents, Strong acids
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
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:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
1.77
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
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.
2,2'-Dipyrrolylmethane

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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：

  2,2'-二吡咯基甲烷 在 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 zinc diacetate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 38.0h， 生成 5,15-di(phenyl)-10-(bromo)-20-(4-benzonitrile)porphyrin zinc(II)
  参考文献：
  名称：

  Novel D–π–A structured Zn(ii)-porphyrin dyes containing a bis(3,3-dimethylfluorenyl)amine moiety for dye-sensitised solar cells

  摘要：

  在 100 mW cmâ2 AM 1.5 G 的模拟光照下，含有多功能共吸附剂的 2FluâZnPâCNâCOOH 染料的短路电流（Jsc）为 15.30 mA cmâ2 ，开路电压（Voc）为 669 mV，填充因子（FF）为 0.71，实现了 7.22% 的高太阳能发电转换效率。

  DOI：

  10.1039/c2cc31384g
• 作为产物：
  描述：

  1,9-diazido-2,8-dimethoxy-nonane-4,6-dione 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到2,2'-二吡咯基甲烷
  参考文献：
  名称：

  甲硅烷基醚和1,3-双-甲硅烷基烯醇醚与1-叠氮基-2,2-二甲氧基乙烷的缩合反应及其后的还原环化反应，合成2-亚烷基吡咯烷，吡咯和吲哚

  摘要：

  1，3-双甲硅烷基烯醇醚与1-叠氮基-2，2-二甲氧基乙烷的缩合和随后的还原环化使得各种2-亚烷基-4-甲氧基吡咯烷的区域和非对映选择性合成成为可能。甲醇的热消除导致官能化吡咯的形成。类似地，制备了2,3,3a，4,5,6-六氢-2,3-苯并吡咯并转化为4,5,6,7-四氢-2,3-苯并吡咯。相反，用三氟乙酸处理2-亚烷基亚吡咯烷导致通过[4 + 2]环加成形成吲哚并随后挤出氮原子。

  DOI：

  10.1021/jo047856x
• 作为试剂：
  描述：

  2-甲基吡咯 在 sodium hydroxide 、 2,2'-二吡咯基甲烷 、 silica gel 、 2,3,4,5,6-pentafluoro-1,1 作用下， 以 二氯甲烷 为溶剂， 以The dipyrromethane (99 μL, 0.8 mmol) thus obtained的产率得到2,2'-二吡咯基甲烷
  参考文献：
  名称：

  Novel expanded porphyrins and process for the synthesis thereof

  摘要：

  由多个吡咯单元交替排列且由甲基桥连的介孔芳基取代扩展卟啉构成，其氢原子被Ar基取代；以及其合成方法。Ar基可以是2,6-取代苯基，可以在其他3、4和5位置具有取代基，也可以是9-蒽基，可以在蒽环的其他位置具有取代基，或者是环己基，在环己基的其他位置具有取代基。上述2和6位置的取代基可以独立选择卤素原子或碳数为1到4的低级烷基，3-5位置、9-蒽基和环己基的取代基可以独立选择由碳数为5或6的取代或非取代烷基、取代或非取代芳基组成的组，除了上述的2和6位置的取代基。每个Ar基可以不同。

  公开号：

  US20030162963A1

文献信息

• [EN] CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE RÉTICULATION ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2021092287A1

  公开（公告）日：2021-05-14

  Compounds of Formula IA, IB, II, III, IV, and/or V are described herein along with their methods of use. A compound of the present invention may cross-link under physiological conditions and/or in vivo.

  本文描述了式IA、IB、II、III、IV和/或V的化合物以及它们的使用方法。本发明的化合物可能在生理条件和/或体内发生交联。
• Porphyrin-Based Conjugated Microporous Polymer Tubes: Template-Free Synthesis and A Photocatalyst for Visible-Light-Driven Thiocyanation of Anilines
  作者：Pengfei Zhang、Yucheng Yin、Zhengxin Wang、Chunyang Yu、Yizhou Zhu、Deyue Yan、Weimin Liu、Yiyong Mai

  DOI：10.1021/acs.macromol.1c00190

  日期：2021.4.13

  photocurrent, compared to those of the irregular solid CMP counterpart. When serving as a metal-free photocatalyst for an undocumented visible-light-driven thiocyanation of anilines, CMP-1 exhibits excellent photocatalytic performance, with single chemoselectivity and high yields for the conversion of 25 types of anilines at ambient conditions. This study fills in the gap of the tubular morphological engineering

  共轭微孔聚合物（CMP）是功能材料的一种重要类型。在这一领域，形态工程仍然是一个重大挑战。在这里，我们报告通过无模板协议基于卟啉的CMP管（CMP-1）的合成。机理研究表明，CMP管是由带状结构的滚动和闭合形成的。与不规则固体CMP对应物相比，这些管具有495 m 2 / g的高比表面积，并具有改进的光学特性，包括在可见光区域的吸收更宽，三重态寿命更长，光电流更稳定。 。当用作无证的可见光驱动的苯胺的硫氰化的无金属光催化剂时，CMP-1具有优异的光催化性能，具有单一的化学选择性和高收率，可在环境条件下转化25种苯胺。这项研究填补了CMP的管状形态工程学的空白，并拓宽了其潜在应用范围。
• 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
• [EN] SELECTIVE PORPHYRIN-CATALYZED ELECTROCHEMICAL REDUCTION OF CO2 INTO CO IN WATER<br/>[FR] RÉDUCTION ÉLECTROCHIMIQUE SÉLECTIVE DU CO2 EN CO DANS L'EAU, CATALYSÉE PAR DES PORPHYRINES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2016124611A1

  公开（公告）日：2016-08-11

  The present invention relates to the use of complexes of water soluble porphyrins of formula (I) below wherein R1 to R10 and R1' to R10' are as defined in claim 1, with iron as catalysts for the selective electrochemical reduction of CO2 into CO, electrochemical cells comprising them, and methods for reducing electrochemically CO2 into CO using said complexes, or said electrochemical cells, thereby producing CO or syngas, in water as the solvent.

  本发明涉及使用以下式（I）中的水溶性卟啉配合物，其中R1至R10和R1'至R10'如权利要求1所定义，以铁作为催化剂，用于将CO2选择性电化学还原为CO，包括它们的电化学电池，以及使用所述配合物或所述电化学电池将CO2电化学还原为CO的方法，从而在水作为溶剂的情况下产生CO或合成气。
• Modular Synthesis of <i>trans</i> ‐A ₂ B ₂ ‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
  作者：Stefan M. Marschner、Ritesh Haldar、Olaf Fuhr、Christof Wöll、Stefan Bräse

  DOI：10.1002/chem.202003885

  日期：2021.1.18

  two decades. Herein we report the synthesis of a large range of 5,15‐bis(4‐ethoxycarbonylphenyl)porphyrin derivatives, through Suzuki and Sonogashira cross‐coupling reactions of an easily accessible corresponding meso‐dibrominated trans‐A2B2‐porphyrin with commercially available boronic acids or terminal alkynes. The resulting porphyrins were fully characterized through NMR, MS, and IR spectroscopy and

  不同功能化的卟啉连接体代表了合成新型卟啉基金属有机框架（MOF）的关键化合物，在过去的二十年中引起了人们的极大兴趣。在此，我们报道了通过易于获得的相应内消旋二溴化反式-A 2 B 2卟啉与市售产品的 Suzuki 和 Sonogashira 交叉偶联反应，合成了多种 5,15-双（4-乙氧基羰基苯基）卟啉衍生物。硼酸或末端炔烃。通过核磁共振、质谱和红外光谱对所得卟啉进行了全面表征，并通过紫外/可见光吸收进行了系统研究。最后，将选定的结构皂化为相应的羧酸，随后证明适合合成表面锚定的 MOF 薄膜。