N-(对甲苯磺酰)-3-吡咯啉 | 16851-72-2

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: N-(对甲苯磺酰)-3-吡咯啉
• 中文别名: 1-(对甲苯磺酰基)-2,5-二氢吡咯；N-(对甲苯磺酰基)-3-吡咯烷；1-(甲苯-4-磺酰基)-2,5-二氢-1H-吡咯；N-对甲苯磺酰-3-吡咯啉
• 英文名称: 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole
• 英文别名: 1-tosyl-2,5-dihydro-1H-pyrrole；N-tosyl-2,5-dihydropyrrole；1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole；2,5-dihydro-1-tosyl-1H-pyrrole；N-tosyl-3-pyrroline；1-(p-toluenesulfonyl)-2,5-dihydropyrrole；1-(p-tosyl)-2,5-dihydro-1H-pyrrole；N-p-tosyl-2,5-dihydro-1H-pyrrole；1-tosyl-2,5-dihydropyrrole；1-tosyl-3-pyrroline；N-(p-Toluenesulfonyl)-3-pyrroline；1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole
• CAS: 16851-72-2
• 化学式: C₁₁H₁₃NO₂S
• mdl: MFCD01321189
• 分子量: 223.296
• InChiKey: UNYMIBRUQCUASP-UHFFFAOYSA-N

物化性质

• 熔点：
  127°C
• 沸点：
  354℃
• 密度：
  1.264
• 闪点：
  168℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26,S36
• 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 |

SDS

N-(p-Toluenesulfonyl)-3-pyrroline Revision number: 5
SAFETY DATA SHEET

---

Section 1. IDENTIFICATION
Product name: N-(p-Toluenesulfonyl)-3-pyrroline

Revision number: 5

---

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.

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: N-(p-Toluenesulfonyl)-3-pyrroline
Percent: >98.0%(GC)
CAS Number: 16851-72-2
Synonyms: N-Tosyl-3-pyrroline
C11H13NO2S
Chemical Formula:

---

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.
N-(p-Toluenesulfonyl)-3-pyrroline

---

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.

---

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:

---

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.

---

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.

---

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.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Almost white
No data available
Odour:
N-(p-Toluenesulfonyl)-3-pyrroline

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:127°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]
Soluble: Hot methanol

---

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, Nitrogen oxides (NOx), Sulfur oxides
products:

---

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

---

Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
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
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

---

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.

---

Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
N-(p-Toluenesulfonyl)-3-pyrroline

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-(对甲苯磺酰)-3-吡咯啉 在 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-对甲苯磺酰吡咯烷
  参考文献：
  名称：

  使用钌卡宾催化剂和硅烷还原烯烃

  摘要：

  在三烷基硅烷的存在下，钌卡宾配合物能够介导烯烃的还原。在这些还原条件下，当动力学有利的闭环复分解是可能的时，可以进行一锅环化还原序列。

  DOI：

  10.1055/s-2005-872695
• 作为产物：
  描述：

  N-(buta-2,3-dien-1-yl)-4-methylbenzenesulfonamide 在 二环己胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以42%的产率得到N-(对甲苯磺酰)-3-吡咯啉
  参考文献：
  名称：

  用于 3-吡咯啉合成的铜催化多米诺同系化和环异构化反应

  摘要：

  发现溴化铜是产生 3-吡咯啉的多米诺反应序列的有效催化剂。Cu(I) 催化炔丙基磺酰胺的 Crabbe 反应和丙二烯中间体的选择性环异构化是使用微波辐射条件进行的，提供了广泛的 2-取代-和 2,5-二取代-3-吡咯啉。反应中间体的机理研究揭示了两种可能的反应途径；两者都提到了乙烯基铜中间体的重要性。

  DOI：

  10.1002/ejoc.201301621
• 作为试剂：
  描述：

  N,N-二烯丙基-4-甲基苯磺酰胺 、 在 silica gel 、 氢气 、 N,N-二烯丙基-4-甲基苯磺酰胺 、 N-(对甲苯磺酰)-2-吡咯啉 、 N-(对甲苯磺酰)-3-吡咯啉 、 title compound 作用下， 以 甲苯 为溶剂， 70.0~260.0 ℃ 、8.0 MPa 条件下， 反应 11.09h， 以8% of 1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole were formed的产率得到N-(对甲苯磺酰)-2-吡咯啉
  参考文献：
  名称：

  Metathesis catalysts

  摘要：

  本发明公开了一种新型的交换催化剂，其化学式为其中R1、R2、R3、R4、R5、R6、X1、X2、L和Y如本文所述，以及制备该催化剂的过程和它们在环闭合或交叉交换反应等交换反应中的应用。

  公开号：

  US07781586B2

文献信息

• Grubbs–Hoveyda type catalysts bearing a dicationic <i>N</i>-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
  作者：Maximilian Koy、Hagen J Altmann、Benjamin Autenrieth、Wolfgang Frey、Michael R Buchmeiser

  DOI：10.3762/bjoc.11.178

  日期：——

  (-)) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was tested in ring opening metathesis polymerization (ROMP) under biphasic conditions using a nonpolar organic solvent (toluene) and the ionic liquid (IL) 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BDMIM(+)][BF4 (-)]. The structure of Ru-2 was confirmed by single crystal X-ray analysis.

  新型二元复分解催化剂[（RuCl2（H2ITapMe2）（= CH-2-（2-PrO）-C6H4））（2+）（OTf（-））2]（Ru-2，H2ITapMe2 = 1,3-bis基于顺式N-杂环卡宾（NHC）配体，制备了（2'，6'-二甲基-4'-三甲基铵苯基）-4,5-二氢咪唑-2-亚烷基，OTf（-）= CF3SO3（-））。使用非极性有机溶剂（甲苯）和离子液体（IL）四氟硼酸1-丁基-2,3-二甲基咪唑鎓[BDMIM（+）] [BF4（- ）]。通过单晶X射线分析确认了Ru-2的结构。
• Monothiolate ruthenium alkylidene complexes with tricyclic fluorinated N-heterocyclic carbene ligands
  作者：Timur R. Akmalov、Salekh M. Masoud、Daria V. Vorobyeva、Fedor M. Dolgushin、Sergey E. Nefedov、Sergey N. Osipov

  DOI：10.1016/j.mencom.2019.01.011

  日期：2019.1

  New monothiolate ruthenium alkylidene complexes bearing bulky tricyclic N-heterocyclic carbene ligands decorated with two geminal trifluoromethyl groups were synthesized. Their catalytic activity in representative olefin metathesis reactions, such as ring closing metathesis of diallyltosylamine and selfmetathesis of allylbenzene, has been evaluated.

  合成了带有两个双基三氟甲基基团的庞大的三环N-杂环卡宾配体的新的单硫醇盐钌亚烷基络合物。已经评估了它们在代表性的烯烃复分解反应中的催化活性，例如二烯丙基糖胺的闭环复分解和烯丙基苯的自我复分解。
• RECYCLABLE METATHESIS CATALYSTS
  申请人：Trustees of Boston College, The

  公开号：US20160168181A1

  公开（公告）日：2016-06-16

  Highly active, recoverable and recyclable transition metal-based metathesis catalysts and their organometallic complexes including dendrimeric complexes are disclosed, including a Ru complex bearing a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and styrenyl ether ligand. The heterocyclic ligand significantly enhances the catalytic activity, and the styrenyl ether allows for the easy recovery of the Ru complex. Derivatized catalysts capable of being immobilized on substrate surfaces are also disclosed. The present catalysts can be used to catalyze ring-closing metathesis (RCM), ring-opening (ROM) and cross metatheses (CM) reactions, and promote the efficient formation of various trisubstituted olefins at ambient temperature in high yield.

  高度活性、可回收和可循环使用的过渡金属基催化剂及其有机金属络合物，包括树枝状络合物被披露，包括一种带有1,3-二甲基-4,5-二氢咪唑-2-亚基和苯乙烯基醚配体的钌络合物。杂环配体显著提高了催化活性，而苯乙烯基醚使得钌络合物易于回收。还披露了能够固定在底物表面的衍生催化剂。所述催化剂可用于催化环闭合烯烃复分解反应(RCM)、环开环反应(ROM)和交叉复分解反应(CM)，并在室温下高效地促进各种三取代烯烃的高产形成。
• Ring‐Closing Olefin Metathesis Catalyzed by Well‐Defined Vanadium Alkylidene Complexes
  作者：Dmitry S. Belov、Gabriela Tejeda、Charlene Tsay、Konstantin V. Bukhryakov

  DOI：10.1002/chem.202005438

  日期：2021.3.8

  selectivity in ring‐opening metathesis polymerization of strained cyclic olefins comparable to those of Ru, Mo, and W catalysts. However, the application of V alkylidenes in routine organic synthesis is limited. Here, we present the first example of ring‐closing olefin metathesis catalyzed by well‐defined V chloride alkylidene phosphine complexes. The developed catalysts exhibit tolerance to various functional

  钒基催化剂在应变环烯烃的开环易位聚合中显示出与Ru，Mo和W催化剂相当的活性和选择性。但是，在常规的有机合成中V亚烷基的应用受到限制。在这里，我们给出了由明确定义的V氯化物亚烷基膦配合物催化的开环烯烃复分解的第一个例子。所开发的催化剂表现出对各种官能团的耐受性，所述官能团例如醚，酯，叔酰胺，叔胺和磺酰胺。亚胺基和膦的大小和给电子性质在活性中间体的稳定性中起着至关重要的作用。
• A simple and practical phase-separation approach to the recycling of a homogeneous metathesis catalyst
  作者：Anna Michrowska、Łukasz Gułajski、Karol Grela

  DOI：10.1039/b517088e

  日期：——

  The air stable asarone-derived Ru carbene 16, a robust olefin metathesis catalyst, can be easily separated after reaction by deposition on silica gel and reused up to nine times. This procedure provides products of excellent purity with low Ru content.

  空气稳定的阿萨酮衍生的Ru卡宾16是一种强健的烯烃复分解催化剂，可通过反应后沉积在硅胶上轻松分离并重复使用多达九次。该方法提供了具有低Ru含量的高纯度产品。

表征谱图