(4-氨基-2.5-二氢-2,2,5,5-四-1H-咪唑-1-基)氧 | 69826-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 中文名称: (4-氨基-2.5-二氢-2,2,5,5-四-1H-咪唑-1-基)氧
• 中文别名: (4-氨基-2.5-二氢-2,2,5,5-四甲基-1H-咪唑-1-基)氧基
• 英文名称: 4-amino-2,5-dihydro-2,2,5,5-tetramethyl-1H-imidazol-1-oxyl
• 英文别名: 4-amino-2,2,5,5-tetramethyl-2,5-dihydroimidazol-1-oxyl；4-amino-2,2,5,5-tetramethyl-3-imidazoline-1-yloxy；4-amino-2,2,5,5-tetramethylimidazol-3-ene-1-yloxy；4-amino-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl；ATI；(4-Amino-2.5-dihydro-2,2,5,5-tetramethyl-1H-imidazol-1-YL)oxy
• CAS: 69826-42-2
• 化学式: C₇H₁₄N₃O
• 分子量: 156.208
• InChiKey: JOUQHALJTYAVRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  225-228 °C
• 沸点：
  280.45°C (rough estimate)
• 密度：
  1.1048 (rough estimate)
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会发生分解。</p>

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：
  0.86
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R36/37/38

SDS

Name:	4-Amino-2,2,5,5-Tetramethyl-3-Imidazoli-ne-1-yloxy, Free Radical, 99% Material Safety Data Sheet
Synonym:	(4-Amino-2.5-Dihydro-2,2,5,5-Tetramethyl-1H-Imidazol-1-yl)oxy.
CAS:	69826-42-2

Section 1 - Chemical Product MSDS Name: 4-Amino-2,2,5,5-Tetramethyl-3-Imidazoli-ne-1-yloxy, Free Radical, 99% Material Safety Data Sheet
Synonym: (4-Amino-2.5-Dihydro-2,2,5,5-Tetramethyl-1H-Imidazol-1-yl)oxy.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
69826-42-2	4-Amino-2,2,5,5-Tetramethyl-3-Imidazol	99	unlisted

Hazard Symbols: XN
Risk Phrases: 40

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Limited evidence of a carcinogenic effect.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. Store at around 20C.

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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# 69826-42-2: 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: Crystalline powder
Color: yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 225.00 - 228.00 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: C7H14N3O
Molecular Weight: 156.21

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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# 69826-42-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Amino-2,2,5,5-Tetramethyl-3-Imidazoline-1-yloxy - 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: XN
Risk Phrases:
R 40 Limited evidence of a carcinogenic effect.
Safety Phrases:
S 28A After contact with skin, wash immediately with plenty of water. S 36/37 Wear suitable protective clothing and gloves. 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# 69826-42-2: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 69826-42-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 69826-42-2 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #4 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (4-氨基-2.5-二氢-2,2,5,5-四-1H-咪唑-1-基)氧 在 1% Pd/C Selcat Q6 、 氢气 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以50%的产率得到4-amino-1-hydroxy-2,2,5,5-tetramethyl-2,5-dihydroimidazole dihydrochloride
  参考文献：
  名称：

  吡咯烷和咪唑啉系列一氧化氮与葫芦[7]脲的包合物

  摘要：

  在分子纳米容器的腔体中包含氮氧化物可能会阻止或显着延迟与细胞还原剂发生的氮氧化物反应，并延长氮氧化物的寿命。本文旨在研究葫芦[7]尿素（CB7）作为pH敏感型氮氧化物探针的分子纳米容器的可能应用。CB7与不同氮氧化物的包合物-3-氨基甲基-脯氨酸（AMP），3-羟甲基-脯氨酸（HMP），4-氨基-2,2,5,5-四甲基-2,5-二氢咪唑-1-氧基（ ATI），以及2,2,4,5,5-五甲基-2,5-二氢咪唑-1-氧基（MTI）。结果发现，可逆形成包合物[电子邮件保护]，苯丙胺的+ @ CB7，[电子邮件保护]，ATIH + @ CB7，和MTIH +@ CB7伴随着氮氧化物基团氮上的超精细相互作用（HFI）常数的降低，以及通过电子顺磁共振（EPR）监测的旋转相关时间的5-7倍增加。确定[电子邮件保护的]配合物的结合常数，并研究了碱金属离子和pH对游离和包封的氮氧化物之间平衡的影响。发现具有

  DOI：

  10.1021/jp9103678

文献信息

• Molecular Design of pH-Sensitive Spin Probes in the 2,3,4,6,7,8-Hexahydro­imidazo[1,5-<i>a</i>]pyrimidine Series with Different Lipophilic/Hydrophilic Properties­
  作者：Vadim K. Khlestkin、Vladimir V. Butakov、Igor A. Grigor’ev、Andrey A. Bobko、Valerii V. Khramtsov

  DOI：10.1055/s-2005-918432

  日期：——

  by the reaction of 4-amino-2,5-dihydro-2,2,5,5-tetramethyl-1H-imidazol-1-oxyl with aminomethylated u,p-unsaturated carbonyl methiodides or hydrochlorides. Introduction of hydrophilic (COOH) or lipophilic (C 1 0 H 2 1 ) groups in the aminomethylated compounds allowed the synthesis of pH-sensitive spin probes with different solubilities.

  新型 pH 敏感自旋探针 - 2,3,4,6,7,8-hexahydro-imidazo[1,5-a]pyrimidines-由 4-amino-2,5-dihydro-2,2 反应合成,5,5-四甲基-1H-咪唑-1-氧基与氨基甲基化的 u,p-不饱和羰基甲硫醚或盐酸盐。在氨基甲基化化合物中引入亲水 (COOH) 或亲油 (C 1 0 H 2 1 ) 基团可以合成具有不同溶解度的 pH 敏感自旋探针。
• Structural Equilibrium in New Nitroxide-Capped Cyclodextrins: CW and Pulse EPR Study
  作者：Olesya A. Krumkacheva、Matvey V. Fedin、Dmitry N. Polovyanenko、Laszlo Jicsinszky、Sylvain R. A. Marque、Elena G. Bagryanskaya

  DOI：10.1021/jp404173j

  日期：2013.7.11

  accessibility of radicals to solvent molecules in studied complexes depending on the structure and length of the linkers. In all studied systems we observed different types of equilibria between conformations with radical fragment being outside the TRIMEB cavity and radical fragment capping the cavity of TRIMEB. The observed guest-induced shift of equilibrium toward the complex with radical capping TRIMEB

  新的自旋标记的环糊精的设计可以显着扩展氮氧化物的功能。使用脉冲和连续波电子顺磁共振（EPR）合成和研究了一系列基于全甲基化环糊精（TRIMEB）的新复合物，该复合物共价结合到哌啶，吡咯啉，吡咯烷和pH敏感的咪唑啉型氮氧化物上。已经研究了自由基和接头性质对形成的配合物结构的影响。使用电子自旋回波包络调制技术，我们已根据连接基团的结构和长度定量分析了研究复合物中自由基对溶剂分子的可及性。在所有研究的系统中，我们观察到构型之间的不同类型的平衡，其中自由基片段位于TRIMEB腔体外部，而自由基片段覆盖TRIMEB腔体。观察到的客体诱导的平衡向带有自由基封端的TRIMEB腔的配合物的转移是由TRIMEB的大环构型变化引起的。对于要求将一氧化氮与TRIMEB包合物配合物紧密定位的应用而言，发现具有-NH-CO-接头配合物的应用前景最为广阔。使用连续波EPR，我们已经表明与TRIMEB共价结合的pH敏感
• Tyrosine-Targeted Spin Labeling and EPR Spectroscopy: An Alternative Strategy for Studying Structural Transitions in Proteins
  作者：Magali Lorenzi、Carine Puppo、Régine Lebrun、Sabrina Lignon、Valérie Roubaud、Marlène Martinho、Elisabetta Mileo、Paul Tordo、Sylvain R. A. Marque、Brigitte Gontero、Bruno Guigliarelli、Valérie Belle

  DOI：10.1002/anie.201102539

  日期：2011.9.19

  Keeping tabs on tyrosine: A three‐component Mannich‐type reaction extends the scope of site‐directed spin labeling by selectively labeling the unique tyrosine residue of CP12 protein (see picture), as was confirmed by mass spectrometry. EPR spectroscopy of the labeled protein showed a very high mobility of the probe, which remained very mobile after complex formation with GAPDH.

  密切关注酪氨酸：三组分曼尼希型反应通过选择性标记CP12蛋白的独特酪氨酸残基来扩大定点自旋标记的范围（见图），这已通过质谱法证实。标记蛋白质的EPR光谱显示探针具有很高的迁移率，与GAPDH形成复合物后，探针仍具有很高的移动性。
• Inclusion Complexes of Nitroxides of Pyrrolidine and Imidazoline Series with Cucurbit[7]uril
  作者：I. Kirilyuk、D. Polovyanenko、S. Semenov、I. Grigor’ev、O. Gerasko、V. Fedin、E. Bagryanskaya

  DOI：10.1021/jp9103678

  日期：2010.2.4

  Inclusion of nitroxides into the cavity of molecular nanocontainers may prevent or significantly retard nitroxide reactions with cellular reductans and increase nitroxide lifetime. This paper is aimed at studying possible applications of cucurbit[7]uril (CB7) as a molecular nanocontainer for pH-sensitive nitroxides probes. Inclusion complexes of CB7 with different nitroxides―3-aminomethyl-proxyl (AMP)

  在分子纳米容器的腔体中包含氮氧化物可能会阻止或显着延迟与细胞还原剂发生的氮氧化物反应，并延长氮氧化物的寿命。本文旨在研究葫芦[7]尿素（CB7）作为pH敏感型氮氧化物探针的分子纳米容器的可能应用。CB7与不同氮氧化物的包合物-3-氨基甲基-脯氨酸（AMP），3-羟甲基-脯氨酸（HMP），4-氨基-2,2,5,5-四甲基-2,5-二氢咪唑-1-氧基（ ATI），以及2,2,4,5,5-五甲基-2,5-二氢咪唑-1-氧基（MTI）。结果发现，可逆形成包合物[电子邮件保护]，苯丙胺的+ @ CB7，[电子邮件保护]，ATIH + @ CB7，和MTIH +@ CB7伴随着氮氧化物基团氮上的超精细相互作用（HFI）常数的降低，以及通过电子顺磁共振（EPR）监测的旋转相关时间的5-7倍增加。确定[电子邮件保护的]配合物的结合常数，并研究了碱金属离子和pH对游离和包封的氮氧化物之间平衡的影响。发现具有