3-氨基-2,2,5,5-四甲基-1-吡咯烷酮 | 34272-83-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-氨基-2,2,5,5-四甲基-1-吡咯烷酮
• 中文别名: 3-氨基-四甲基-1-吡咯烷酮
• 英文名称: 2,2,5,5-tetramethyl-3-aminopyrrolidine-1-oxyl
• 英文别名: 3-amino-2,2,5,5-tetramethylpyrrolidin-1-oxyl；3-amino-PROXYL；3-amino-2,2,5,5-tetramethylpyrrolidine-1-oxyl；3-amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy；2,2,5,5-Tetramethyl-3-amino-pyrrolidin-1-oxyl
• CAS: 34272-83-8
• 化学式: C₈H₁₇N₂O
• 分子量: 157.236
• InChiKey: CGKOJRBANWWHCG-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  75-80 °C (1 mmHg)
• 密度：
  1.0152 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R20/21/22,R34
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	3-Amino-2 2 5 5-Tetramethyl-1-Pyrrolidinyloxy 99% (Titr.) Material Safety Data Sheet
Synonym:	None known
CAS:	34272-83-8

Section 1 - Chemical Product MSDS Name:3-Amino-2 2 5 5-Tetramethyl-1-Pyrrolidinyloxy 99% (Titr.) Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
34272-83-8	3-Amino-2,5,5,5-Tetramethyl-1-Pyrrolid	99	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 34272-83-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: almost white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 45 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H17N2O
Molecular Weight: 157.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 34272-83-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Amino-2,5,5,5-Tetramethyl-1-Pyrrolidinyloxy - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 34272-83-8: No information available.
Canada
CAS# 34272-83-8 is listed on Canada's NDSL List.
CAS# 34272-83-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 34272-83-8 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氨基-2,2,5,5-四甲基-1-吡咯烷酮 在 Fe(II)- EDTA 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-(2-Hydroxy-1'-methoxy-2',2',5',5'-tetramethyl-3-oxo-4-phenyl-2,3,2',3',4',5'-hexahydro-1'H-[1,3']bipyrrolyl-2-yl)-benzoic acid
  参考文献：
  名称：

  痕量测定生物系统中的羟基自由基。

  摘要：

  描述了一种简单且高度灵敏的方法，用于量化生物系统中OH的产生速率。该方法利用OH和二甲基亚砜之间的反应定量地产生甲基，然后该甲基与氟胺衍生的氮氧化物反应以生成稳定的O-甲基羟胺。通过反相高效液相色谱分离该O-甲基羟胺，并进行荧光定量。对于50微升注射，信噪比为2时，O-甲基羟胺的估计检出限为3.5 nM。该方法适用于测定生物学相关模型系统和小鼠表皮中OH的产生速率醌抗癌化合物处理过的细胞系。

  DOI：

  10.1021/ac970622b
• 作为产物：
  描述：

  四甲基哌啶酮 在 镍 sodium tungstate 、 sodium hypobromide 、 ammonium acetate 、 氢气 、 双氧水 、 溴 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 3-氨基-2,2,5,5-四甲基-1-吡咯烷酮
  参考文献：
  名称：

  Influerce of chemical structure of nitroxyl spin labels on their reduction by ascorbic acid

  摘要：

  DOI：

  10.1016/s0040-4020(01)96516-0

文献信息

• Reaction of Nitroxides with Sulfur Containing Compounds II [1]. Preparation of Nitroxides Bearing an Isothiocyanate Substituent in View of the Nitroxyl Group Reduction with Thiophosgene
  作者：Jerzy Zakrzewski、Jaros?aw Hupko、Krzysztof Kryczka

  DOI：10.1007/s00706-002-0572-x

  日期：2003.5.1

   The reaction of thiophosgene with 2,2,6,6-tetramethylpiperidine-1-oxyl (used as a model nitroxyl radical) was examined. 2,2,6,6-Tetramethylpiperidine and 2,2,6,6-tetramethyl-1-hydroxypiperidine were identified as products. The reaction is not competitive with the reaction of thiophosgene with an amino group. Thus, three nitroxides with an isothiocyanate group were synthesized from thiophosgene and

   考察了硫光气与2,2,6,6-四甲基哌啶-1-氧基（用作模型硝基氧基）的反应。鉴定出2,2,6,6-四甲基哌啶和2,2,6,6-四甲基-1-羟基哌啶为产物。该反应与硫光气与氨基的反应没有竞争性。因此，由硫光气和含有氨基取代基的氮氧化物合成了具有异硫氰酸酯基的三种氮氧化物。
• Synthesis of Next-Generation Maleimide Radical Labels
  作者：Janet Lovett、Bouchra Hajjaj、Anokhi Shah、Stacey Bell、Sally Shirran、Catherine Botting、Alexandra Slawin、Alison Hulme

  DOI：10.1055/s-0035-1562451

  日期：——

  The synthesis and characterization of four new nitroxide-radical-containing next-generation maleimides are presented. Each new label has a single leaving group which is either a phenoxyl or bromide. The linker between the maleimide and the nitroxide-containing framework is either a racemic mixture of a short chain or an achiral longer chain. These molecules have been designed to site-specifically label

  介绍了四种新的含氮氧自由基的下一代马来酰亚胺的合成和表征。每个新标签都有一个单独的离去基团，即苯氧基或溴化物。马来酰亚胺和含氮氧化合物骨架之间的接头是短链或非手性长链的外消旋混合物。这些分子已被设计为在用于磁共振研究的蛋白质中位点特异性地标记邻近半胱氨酸。最终产品的表征包括晶体学和抹香鲸肌红蛋白的标记。
• Preparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium Relationship
  作者：James M. Bobbitt、Nicholas A. Eddy、Clyde X. Cady、Jing Jin、Jose A. Gascon、Svetlana Gelpí-Dominguez、Jerzy Zakrzewski、Martha D. Morton

  DOI：10.1021/acs.joc.7b00846

  日期：2017.9.15

  homologous nitroxide radicals have been prepared and characterized. The oxidation properties of the salts have been explored. The direct 13C NMR and EPR spectra of the nitroxide free radicals and the oxoammonium salts, along with TEMPO and its oxoammonium salt, have been successfully measured with little peak broadening of the NMR signals. In the spectra of all ten compounds (nitroxides and corresponding

  制备并表征了三种新的同源TEMPO氧铵盐和三个同源的氮氧自由基。已经探索了盐的氧化性质。直接13已成功测量了氮氧化物自由基和氧代铵盐以及TEMPO及其氧代铵盐的C NMR和EPR光谱，而NMR信号的峰展宽很小。在所有十种化合物（氮氧化物和相应的氧铵盐）的光谱中，2,2,6,6-四甲基哌啶核中的碳均未出现，表明其具有顺磁性。氧铵盐溶液中这种不可预测的整体顺磁性是由氧化还原平衡所解释的，如氧铵盐和痕量相应的一氧化氮之间所示。该平衡通过具有N-乙酰基取代基的氮氧化物与具有较长酰基侧链的氧铵盐之间的电子交换反应得以证实。
• Use of the Mannich Reaction to Synthesize Spin-Labeled Derivatives of the Natural Flavonoid Dihydroquercetin
  作者：N. V. Kosheleva、E. I. Chernyak、Yu. F. Polienko、S. V. Morozov、I. A. Grigor̕ev

  DOI：10.1007/s10600-014-0927-7

  日期：2014.5

  Mono-substituted spin-labeled compounds were synthesized from Mannich reactions of dihydroquercetin with 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl, 3-amino-2,2,5,5-tetramethylpyrrolidine-1-oxyl, and 3-aminomethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl. According to preliminary data, the compounds possessed antioxidant activity and selective cytotoxicity against various tumor cells and were promising for biomedical tests including magnetic resonance tomography.

  合成了单取代的自旋标记化合物，这些化合物是通过二氢槲皮素与4-氨基-2,2,6,6-四甲基哇尔喹咯-1-氧基、3-氨基-2,2,5,5-四甲基吡咯-1-氧基和3-氨基甲基-2,2,5,5-四甲基吡咯-1-氧基的曼尼赫反应合成的。根据初步数据，这些化合物具有抗氧化活性，并对各种肿瘤细胞表现出选择性的细胞毒性，且在生物医学测试中，包括磁共振成像方面具有良好前景。
• Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates
  作者：Jerzy Zakrzewski、Bogumiła Huras、Anna Kiełczewska、Maria Krawczyk、Jarosław Hupko、Katarzyna Jaszczuk

  DOI：10.3390/molecules24132457

  日期：——

  The reactions of 3-isoselenocyanato-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 3-isoselenocyanatomethyl-2,2,5,5-tetramethyl-3-pyrrolidine-1-oxyl, and 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and alcohols give the corresponding novel nitroxyl selenoureas and selenocarbamates, all bearing a nitroxyl moiety. Synthesized selenoureas and selenocarbamates show significant

  3-异硒氰基-2,2,5,5-四甲基吡咯烷-1-氧基、3-异硒氰基甲基-2,2,5,5-四甲基-3-吡咯烷-1-氧基和4-异硒氰基-2的反应， 2,6,6-四甲基哌啶-1-氧基与选定的胺和醇产生相应的新型硝酰基硒脲和硒代氨基甲酸酯，它们都带有硝酰基部分。合成的硒脲和硒代氨基甲酸盐对病原真菌和细菌具有显着的活性。与哌啶硝基氧化物相比，吡咯烷、五元硝酰基硒脲和硒代氨基甲酸酯分别对病原真菌和细菌表现出优异的抗真菌和抗菌活性。