1-羟基-2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物 | 18796-01-5

• 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: 1-羟基-2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物
• 英文名称: 1-hydroxy-2,2,5,5-tetramethyl-4-phenyl-3-imidazoline-3-oxide
• 英文别名: 2,2,5,5-Tetramethyl-4-phenyl-1-imidazolidinol 3-oxide；3-hydroxy-2,2,4,4-tetramethyl-1-oxido-5-phenylimidazol-1-ium
• CAS: 18796-01-5
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: MLSJXLQAJPYPSI-UHFFFAOYSA-N

物化性质

• 熔点：
  188-194 °C
• 沸点：
  376.62°C (rough estimate)
• 密度：
  1.0844 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933290090
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	1-Hydroxy-2 2 5 5-tetramethyl-4-phenyl-3- imidazoline-3-oxide Material Safety Data Sheet
Synonym:
CAS:	18796-01-5

Section 1 - Chemical Product MSDS Name:1-Hydroxy-2 2 5 5-tetramethyl-4-phenyl-3- imidazoline-3-oxide Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18796-01-5	1-Hydroxy-2,2,5,5-tetramethyl-4-phenyl	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.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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 or absorb material, then place into a suitable clean, dry, closed 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.

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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# 18796-01-5: 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:
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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 188.6 - 189.6 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: C13H18N2O2
Molecular Weight: 234.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 18796-01-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Hydroxy-2,2,5,5-tetramethyl-4-phenyl-3- imidazoline-3-oxid - 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# 18796-01-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 18796-01-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18796-01-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-羟基-2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物 在 lead dioxide 作用下， 以 丙酮 为溶剂， 生成 2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物-1-氧基
  参考文献：
  名称：

  Influence of radical center on oxidative properties of nitron group in reaction of nitroxyl radicals of 3-imidazoline 3-oxide withhydrazine

  摘要：

  DOI：

  10.1007/bf00956162
• 作为产物：
  描述：

  2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物-1-氧基 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 、 苯乙炔 作用下， 以 苯 为溶剂， 反应 5.0h， 以66%的产率得到1-羟基-2,2,5,5-四甲基-4-苯基-3-咪唑啉-3-氧化物
  参考文献：
  名称：

  3-咪唑啉系列的硝基氧基与末端炔的交叉偶联的合成和机理方面

  摘要：

  通过3-咪唑基卤化物与末端炔烃或它们的铜盐的交叉偶联反应，开发了用于新型3-咪唑基-3-氧化物-1-氧基的炔属衍生物的实用合成方法，包括双自由基。硝氧基官能团作为内部氧化剂的存在导致交叉偶联产物的形成与氧化均偶联产物之间的竞争。通过包括催化剂的性质，卤化物的反应性和反应条件在内的多种因素的组合，可以使竞争中的平衡向交叉偶联产物转移。

  DOI：

  10.1016/j.tet.2008.06.088

文献信息

• Ammounium acetate as a catalyst of the condensation of sterically hindered functionalized hydroxylamines with ketones
  作者：V. A. Reznikov、L. B. Volodarsky

  DOI：10.1007/bf02502943

  日期：1997.9

  Ammonium acetate was found to be a catalyst of the condensation of α-hydroxylamino oximes and α-hydroxylamino alcohols with ketones. This condensation leads to sterically hindered heterocyclic hydroxylamines, which are precursors of stable nitroxides.

  发现乙酸铵是 α-羟基氨基肟和 α-羟基氨基醇与酮缩合的催化剂。这种缩合导致空间位阻杂环羟胺，它是稳定的氮氧化合物的前体。
• Interaction of heterocyclic nitrones with organometallic reagents as a method for the synthesis of new types of nitroxides
  作者：Vladimir A. Reznikov、Leonid B. Volodarsky

  DOI：10.1016/s0040-4020(01)81557-x

  日期：1993.1

  The reactions of heterocyclic nitroxides: 3-imidazoline-3-oxides, 2H- (4H)-imidazole mono- and dioxides, dihydropyrazine-1,4-dioxides, with organometallic reagents and subsequent oxidation led to heterocyclic nitroxides of 3-(2)-imidazoline and 3-(2)-imidazoline-3-oxide, dihydropyrazine oxide, monocyclic imidazolidine biradicals and stable acyclic nitroxides with hydrogen at the α-carbon atom.

  杂环氮氧化物的反应：3-咪唑啉-3-氧化物，2H-（4H）-咪唑单和二氧化物，二氢吡嗪-1,4-二氧化物与有机金属试剂的反应以及随后的氧化反应生成3-（2）杂环氮氧化物-咪唑啉和3-（2）-咪唑啉-3-氧化物，二氢吡嗪氧化物，单环咪唑烷双自由基和稳定的无环氮氧化物，氢在α-碳原子处。
• Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds
  作者：Sergei F. Vasilevsky、Olga L. Krivenko、Igor V. Alabugin

  DOI：10.1016/j.tetlet.2007.09.031

  日期：2007.11

  In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI–PPh3–K2CO3–DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the

  在Pd催化剂存在下，即使不存在Cu（II）添加剂，3-咪唑啉硝基氧基也会促进末端炔烃的氧化偶联（二聚）。另一方面，无钯的CuI–PPh 3 –K 2 CO 3 –DMF催化体系导致1-羟基-4- [2-（对-碘苯基）乙烯基] -2,2的有效交叉偶联。，5,5-四甲基-3-咪唑啉-3-氧化物与末端芳基和杂芳基乙炔形成4- [2-（芳基/杂芳基乙炔基）苯基]乙烯基] -2,2,5,5-四甲基-3 -咪唑啉-3-氧化物-1-氧基的产率为70-75％。
• Nitration of imidazoline-n-oxide nitroxides containing the aryl nitrone group
  作者：L.B. Volodarsky、I.A. Grigor'ev、L.N. Grigor'eva、I.A. Kirilyuk

  DOI：10.1016/s0040-4039(01)81692-0

  日期：1984.1

  Nitration of 4-aryl-3-imidazoline-3-oxide nitroxyl radicals leads to 4-nitroaryl-3-imidazoline-3-oxide nitroxides via oxammonium salts formation, the nitrone group being an ortho-para orientant.

  通过芳族铵盐的形成，对4-芳基-3-咪唑啉-3-氧化物硝基氧基的硝化导致4-硝基芳基-3-咪唑啉-3-氧化物硝基氧化物，其中的硝酮基是邻位对位取向的。
• Inhibition of pulp and paper yellowing using nitroxides, hydroxylamines and other coadditives
  申请人：——

  公开号：US20020124980A1

  公开（公告）日：2002-09-12

  Pulps or papers, especially chemimechanical or thermomechanical pulps or papers, which still contain lignin, have enhanced resistance to yellowing when they contain an effective stabilizing amount of a hindered amine compound which preferably is a nitroxide, a hydroxylamine or an ammonium salt thereof. This performance is often further enhanced by the presence of one or more coadditives selected from the group consisting of the UV absorbers, the polymeric inhibitors, the nitrones, the fluorescent whitening agents, metal chelating agents, sulfur containing stabilizers, metal salts and diene compounds. Combinations of nitroxides, hydroxylamines or their salts, benzotriazole or benzophenone UV absorbers and a metal chelating agent are particularly effective. Selected derivatives of 1-oxyl-2,2,6,6-tetramethyl-piperidin-4-ol and selected hydroxylamine salts are novel compounds and are surprisingly effective for this purpose.

  含有木质素的纸浆或纸张，特别是化学机械或热机械纸浆或纸张，如果它们含有有效的阻化胺化合物（最好是亚硝基自由基，羟胺或其铵盐），则具有增强的抗黄变性能。当与来自紫外线吸收剂、聚合抑制剂、亚硝基醇、荧光增白剂、金属螯合剂、含硫稳定剂、金属盐和二烯化合物等组成的一种或多种协同添加剂一起使用时，通常可以进一步提高其性能。亚硝基自由基、羟胺或其盐、苯并三唑或苯并酚类紫外线吸收剂和金属螯合剂的组合尤其有效。选择的1-氧基-2,2,6,6-四甲基哌啶-4-醇和选择的羟胺盐衍生物是新的化合物，出乎意料地有效。