2,2,5,5-四甲基-3-吡咯啉-1-氧基-3-羧酸正羟基琥珀酰亚胺酯 | 37558-29-5

• 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 - 吡咯啉
• 中文名称: 2,2,5,5-四甲基-3-吡咯啉-1-氧基-3-羧酸正羟基琥珀酰亚胺酯
• 中文别名: 2,2,5,5-四甲基-3-吡咯啉-1-氧基-3-羧酸N-羟基琥珀酰；2,2,5,5-四甲基-3-吡咯啉-1-氧基-3-羧酸 N-羟基琥珀酰
• 英文名称: 1-oxyl-2,2,5,5-tetramethylpyrroline-3-carboxylate N-hydroxysuccinimide ester
• CAS: 37558-29-5
• 化学式: C₁₃H₁₇N₂O₅
• 分子量: 281.288
• InChiKey: IWVOZPVFXICWQH-UHFFFAOYSA-N

物化性质

• 熔点：
  175-178 °C
• 溶解度：
  甲醇
• 稳定性/保质期：

  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25

SDS

Name:	2 2 5 5-Tetramethyl-3-Pyrrolin-1-Oxyl-3-Carboxylic Acid Material Safety Data Sheet
Synonym:	None
CAS:	37558-29-5

Section 1 - Chemical Product MSDS Name:2 2 5 5-Tetramethyl-3-Pyrrolin-1-Oxyl-3-Carboxylic Acid Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
37558-29-5	2,2,5,5-Tetramethyl-3-Pyrrolin-1-Oxyl-	ca 100	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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 37558-29-5: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 173.50 - 176.50 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H17N2O5
Molecular Weight: 281.28

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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:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 37558-29-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,2,5,5-Tetramethyl-3-Pyrrolin-1-Oxyl-3-Carboxylic Acid N-Hydroxysuccinimide Ester - 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# 37558-29-5: No information available.
Canada
CAS# 37558-29-5 is listed on Canada's NDSL List.
CAS# 37558-29-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 37558-29-5 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：

  2,2,5,5-四甲基-3-吡咯啉-1-氧基-3-羧酸正羟基琥珀酰亚胺酯 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3-(6-(β-D-ribofuranos-1'-yl)-7-thioxo-6,7-dihydrothieno[2,3-c]pyridin-4-yl)-prop-2-ynyl)-amide
  参考文献：
  名称：

  通过遗传字母扩展转录实现的长非编码RNA的EPR距离测量。

  摘要：

  我们在这里提出了一种新型的含氮氧化物自旋标记的RNA三磷酸TPT3NO及其通过扩展的遗传字母通过体外转录对RNA进行位点特异性自旋标记的应用。我们的策略允许通过标准的体外转录轻松制备自旋标记的RNA，大小从短RNA寡核苷酸到大而复杂的RNA分子（超过370个核苷酸）。作为概念的证明，通过脉冲电子顺磁共振（EPR）光谱测量短自互补RNA序列和经过充分研究的185个核苷酸的非编码RNA枯草芽孢杆菌glmS核酶的自旋间距离分布。然后，该方法首次用于通过PELDOR探测长的非编码RNA Xist的377个核苷酸A区的折叠。

  DOI：

  10.1002/anie.201916447

文献信息

• Synthesis of Water Soluble Spin Labeled Glucose Derivatives as Potential NMR Contrast Enhancing Agents
  作者：George Sosnovsky、N. Uma Maheswara Rao、Jan Lukszo、Robert C. Brasch

  DOI：10.1515/znb-1986-1017

  日期：1986.10.1

  methodologies for the preparation of nitroxyl labeled derivatives of D -(+)-glucose, α -D -(+)-m ethylglycoside, 2-amino-2-deoxy-D -(+)-glucose, and D -(+)-glucuronic acid are presented. The spin labels in these compounds are attached variably at the 1, 2, 3, and 6 positions of the glucose framework. These new compounds, being water soluble and producing marked enhancement of spin-lattice (T ,) and spin-spin

  摘要 制备 D -(+)-葡萄糖、α -D -(+)-m 乙基糖苷、2-氨基-2-脱氧-D -(+)-葡萄糖和 D -( +)-葡糖醛酸被呈现。这些化合物中的自旋标记可变地连接在葡萄糖框架的 1、2、3 和 6 位。这些新化合物是水溶性的，可显着增强去离子水和人血浆中的自旋晶格 (T1) 和自旋自旋 (T2) 质子弛豫，具有作为磁共振成像对比度改变药物和自旋探针的潜在用途。生物分子研究。这些自旋标记的碳水化合物可能表现出反映葡萄糖代谢中组织特异性差异的体内生物分布特征。
• New antiarrhythmic agents. 2,2,5,5-Tetramethyl-3-pyrroline-3-carboxamides and 2,2,5,5-tetramethylpyrrolidine-3-carboxamides.
  作者：Olga H. Hankovsky、Kalman Hideg、Ilona Bodi、Laszlo Frank

  DOI：10.1021/jm00157a005

  日期：1986.7

  by forming the Schiff bases and subsequent sodium borohydride reduction. Other tetramethyl-3-pyrrolinecarboxamide compounds were synthesized by acylating the aminoalkyl compounds with 2,2,6,6-tetramethyl-3,5-dibromo-4-piperidinone in a reaction involving Favorskii rearrangement. Saturation of the double bond of some pyrroline derivatives furnished the pyrrolidinecarboxamides. The new compounds of each

  N-（ω-氨基烷基）-2,2,5,5-四甲基-3-吡咯啉或-吡咯烷-3-羧酰胺通过反应性酸衍生物（酰氯，活化的酯，邻苯二甲酸酐，邻苯二甲酰亚胺，2-烷基-4H-3,1-苯并恶嗪-4-酮）或通过形成席夫碱和随后的硼氢化钠还原将它们烷基化。通过在涉及Favorskii重排的反应中将氨基烷基化合物与2,2,6,6-四甲基-3,5-二溴-4-哌啶酮酰化来合成其他四甲基-3-吡咯啉羧酰胺化合物。一些吡咯啉衍生物的双键的饱和提供了吡咯烷甲酰胺。每种类型的新化合物对乌头碱引起的心律失常均具有活性，其中一些具有比奎尼丁更高的活性和更好的化疗指数。从每种类型的活性新化合物中选出的一些实例显示出对哇巴因引起的心律不齐具有强活性。为了进行比较，选择了已知的药物，如利多卡因，美西律和托卡尼特。最有效的化合物被氧化为顺磁性氮氧化物，后者被还原为N-羟基衍生物。这些产品没有或仅有减少的抗心律失常作用。
• Synthesis of Structurally Defined Nitroxide Spin-Labeled Glycolipids as Useful Probes for Electron Paramagnetic Resonance (EPR) Spectroscopy Studies of Cell Surface Glycans
  作者：Zhongwu Guo、Xin Yan

  DOI：10.1055/a-1768-2138

  日期：2022.6

  functionalized free glycans as the last synthetic step. These glycolipids are useful probes for the study of cell surface glycans by electron paramagnetic resonance spectroscopy. Moreover, the key synthetic intermediates, free glycolipids carrying a flexible azido group at the glycan non-reducing end, are widely useful platforms for accessing glycolipids with other molecular labels.

  设计了四种携带不同聚糖和在聚糖非还原端具有硝基氧自由基自旋的糖脂，并通过有效和简化的合成策略从游离葡萄糖和麦芽寡糖中合成。这种合成策略的主要特征包括游离碳水化合物的区域选择性功能化以及作为最后合成步骤的自由基自旋标记与功能化游离聚糖的偶联。这些糖脂是通过电子顺磁共振光谱研究细胞表面聚糖的有用探针。此外，关键的合成中间体，即在聚糖非还原端带有柔性叠氮基的游离糖脂，是获取具有其他分子标记的糖脂的广泛有用的平台。
• Precipitation-free high-affinity multivalent binding by inline lectin ligands
  作者：Philipp Rohse、Sabrina Weickert、Malte Drescher、Valentin Wittmann

  DOI：10.1039/d0sc01744b

  日期：——

  precipitating binding mode. Here, we present a new design of high-potency multivalent ligands featuring an inline arrangement of ligand epitopes with exceptionally high binding affinities in the low nanomolar range. At the same time, we show with a multi-methodological approach that precipitation of the receptor is prevented. We distinguish distinct binding modes of the ligands, in particular we elucidate

  多价配体与蛋白质的相互作用是生物学介导的重要概念，例如信号传导和粘附。多价配体通常具有极大增加的结合亲和力。但是，它们也会引起受体分子的交联，从而导致配体-受体复合物沉淀。由沉淀引起的斑块形成是许多致命疾病的已知特征，其限制了具有沉淀结合模式的多价配体的潜在医学应用。在这里，我们提出了一种新的高效多价配体设计，其特征是配体表位的内联排列，在低纳摩尔范围内具有异常高的结合亲和力。同时，我们采用多方法论方法表明可以防止受体沉淀。我们区分了配体的不同结合方式，特别地，我们阐明了独特的螯合结合模式，其中四个受体结合位点同时被一个多价配体分子桥接。我们为经过充分研究的模型凝集素小麦胚芽凝集素建立的内联多价配体的新设计概念，对于开发作为未来疗法的高效多价抑制剂具有巨大潜力。
• Novel pH-sensitive nitroxide di- and tri-radical spin labels
  作者：Vladimir V. Martin、John F. W. Keana

  DOI：10.1039/c39950000723

  日期：——

  Stable nitroxide di- and tri-radicals 2–4, synthesized from diethylenetriamine or tris(aminoethyl)amine, display pH-sensitive EPR spectra owing to changes in through-space exchange upon protonation of the central amine nitrogen atom.

  由二乙烯三胺或三（氨基乙基）胺合成的稳定的亚硝基二和三自由基 2-4，由于中心胺氮原子的质子化导致通过空间交换的变化，显示出对 pH 敏感的 EPR 光谱。