苯基吖啶-9-羧酸酯 | 109392-90-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 苯基吖啶-9-羧酸酯
• 中文别名: 9-吖啶羧酸苯酯
• 英文名称: phenyl acridine-9-carboxylate
• 英文别名: 9-(phenoxycarbonyl)-acridine；phenyl 9-acridinecarboxylate
• CAS: 109392-90-7
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: QIYUZWMXMSNPRG-UHFFFAOYSA-N

物化性质

• 熔点：
  188-192 °C
• 沸点：
  440.65°C (rough estimate)
• 密度：
  1.2079 (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)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于阴凉干燥处

SDS

Name:	Phenyl Acridine-9-Carboxylate Material Safety Data Sheet
Synonym:	None
CAS:	109392-90-7

Section 1 - Chemical Product MSDS Name:Phenyl Acridine-9-Carboxylate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
109392-90-7	Phenyl Acridin	ca 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes 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: Immediately 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:
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:
Treat symptomatically and supportively.

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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. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation.
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# 109392-90-7: 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: tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 190 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: C20H13NO2
Molecular Weight: 299.32

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
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# 109392-90-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phenyl Acridin - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
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# 109392-90-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 109392-90-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 109392-90-7 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：

  苯基吖啶-9-羧酸酯 在 四丁基氢氧化铵 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 9-acridinepercarboxylic acid
  参考文献：
  名称：

  涉及酸性和环境离子发光体的化学发光。9-吖啶过羧酸根阴离子的化学发光

  摘要：

  9-吖啶羧酸苯酯与过量的过氧化离子在 THF/水 (67/33 mol%) 中的反应导致发射亮黄绿色光或亮蓝色光，具体取决于反应条件。例如，高浓度的过氧化氢和水有利于蓝色发射。9-吖啶过羧酸是反应中常见的中间体。负责蓝色化学发光的发光体是吖啶酮，而负责黄绿色化学发光的发光体是吖啶酮的阴离子。碱浓度和溶剂组成对这两种发射体的相对比例的影响已经证明，与简单理论的预期相反，二氧杂环丁酮不是反应中的中间体。

  DOI：

  10.1021/ja00251a024
• 作为产物：
  描述：

  9-吖啶羧酸 在 氯化亚砜 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 苯基吖啶-9-羧酸酯
  参考文献：
  名称：

  涉及酸性和环境离子发光体的化学发光。9-吖啶过羧酸根阴离子的化学发光

  摘要：

  9-吖啶羧酸苯酯与过量的过氧化离子在 THF/水 (67/33 mol%) 中的反应导致发射亮黄绿色光或亮蓝色光，具体取决于反应条件。例如，高浓度的过氧化氢和水有利于蓝色发射。9-吖啶过羧酸是反应中常见的中间体。负责蓝色化学发光的发光体是吖啶酮，而负责黄绿色化学发光的发光体是吖啶酮的阴离子。碱浓度和溶剂组成对这两种发射体的相对比例的影响已经证明，与简单理论的预期相反，二氧杂环丁酮不是反应中的中间体。

  DOI：

  10.1021/ja00251a024

文献信息

• Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study
  作者：Manabu Nakazono、Yuji Oshikawa、Mizuho Nakamura、Hidehiro Kubota、Shinkoh Nanbu

  DOI：10.1021/acs.joc.6b02748

  日期：2017.3.3

  mechanism was composed of the nucleophilic addition reaction of hydroperoxide anion, dioxetanone ring formation, and nonadiabatic transition due to spin–orbit coupling around the transition state (TS) to the triplet state (T1) following the decomposition pathway. The TS which appeared in the thermal decomposition would be a rate-determining step for all three processes.

  合成了具有苯基和联苯基部分的各种新型a啶鎓酯衍生物，并研究了它们的最佳化学发光条件。发现了几种在中性条件下强烈化学发光的cri啶鎓酯，然后将这些衍生物用于检测过氧化氢和葡萄糖。具有强吸电子基团如氰基，甲氧羰基，和硝基在苯基部分的4-位上的苯基-10-甲基吖啶10λ酯4吖啶-9-羧酸盐三氟甲磺酸显示出强的化学发光强度。的化学发光强度3,4-二氰基苯基-10-甲基10λ 4吖啶-9-羧酸盐三氟甲磺酸较苯基-10-甲基10λ的强约100倍4在pH为7的过氧化氢和葡萄糖的线性校准范围吖啶-9-羧酸盐三氟甲磺酸使用0.05〜10 mM和10-2000μM3,4-（二甲氧基羰基）苯基-10-甲基10λ 4 -acridine- 9-羧酸盐三氟甲磺酸盐分别在pH 7和pH 7.5下。通过密度泛函理论的量子化学计算，评价了proposed啶鎓酯通过二氧杂环丁酮结构的化学发光反应机理。所提出的机理是由氢过氧
• Spectral features of substituted 9-(phenoxycarbonyl)-acridines and their protonated and methylated cation derivatives
  作者：Karol Krzymiński、Alexander D. Roshal、Agnieszka Niziołek

  DOI：10.1016/j.saa.2007.10.045

  日期：2008.7

  The long-wavelength absorption of eight 9-(phenoxycarbonyl)-acridines and the 10-H-9-(phenoxycarbonyl)-acridinium and 10-methyl-9-(phenoxycarbonyl)-acridinium cations derived from them, substituted with an alkyl or trifluoroalkyl group at the benzene ring, occurs above 300 nm as the superposition of four bands. Three of these bands occupy comparable positions (expressed in nm) in all the compounds;

  从烷基或三氟烷基取代的8个9-（苯氧羰基）-ac啶和10-H-9-（苯氧羰基）-rid啶鎓和10-甲基-9-（苯氧羰基）-ac啶鎓阳离子的长波吸收苯环上的基团出现在300 nm以上，是四个谱带的重叠。在所有化合物中，这些带中的三个占据了相当的位置（以nm表示）。然而，第四种改变了位置，在中性分子中以低于400 nm的长波肩出现，但在阳离子中以高于400 nm的近乎独立的谱带出现。在长波长吸收带内激发产生的弱荧光相对于吸收发生红移，因此中性分子和阳离子的斯托克斯频移相似。斯托克斯位移倾向于随介质的定向极化率而增加。计算预测，长波长电子跃迁伴随着分子的结构变化。他们还表明，在这种跃迁之后，整个分子中的电子密度将发生大致均匀的变化，同时偶极矩也会发生细微变化，这说明了长波长区域的吸收较弱。预测的辐射失活速率常数和非辐射失活速率常数表明，在研究的分子中发生了有效的自旋-轨道耦合，这是荧光量子产率相
• Chemiluminogenic Features of 10-Methyl-9-(phenoxycarbonyl)acridinium Trifluoromethanesulfonates Alkyl Substituted at the Benzene Ring in Aqueous Media
  作者：Karol Krzymiński、Agnieszka Ożóg、Piotr Malecha、Alexander D. Roshal、Agnieszka Wróblewska、Beata Zadykowicz、Jerzy Błażejowski

  DOI：10.1021/jo1020882

  日期：2011.2.18

  electronically excited 10-methyl-9-acridinone, whose relaxation was accompanied by chemiluminescence (CL). The kinetic constants of CL decay, relative efficiencies of light emission, chemiluminescence quantum yields, and resistance toward alkaline hydrolysis were determined experimentally under various conditions. The mechanism of CL generation is considered on the basis of thermodynamic and kinetic parameters

  合成，纯化和鉴定了在苯环上带有烷基取代基的10-甲基-9-（苯氧羰基）ac基三氟甲烷磺酸盐。在与OOH的反应中-在碱性水性介质中，所研究化合物的阳离子被转化为电子激发的10-甲基-9-ac啶酮，其弛豫伴随着化学发光（CL）。在各种条件下，通过实验确定了CL衰减的动力学常数，相对发光效率，化学发光量子产率以及对碱水解的抵抗力。根据在DFT理论水平预测的反应步骤的热力学和动力学参数，考虑了CL生成的机理。化学发光效率是通过在OOH亲核取代之间C（9）的电中心的竞争的结果-或者OH -以及由此形成的中间体分解为电子激发的10-甲基-9-ac啶酮的能力。鉴定稳定的和中间的反应产物证实了建议的反应方案。获得的结果，尤其是“有用性”参数的依赖性（考虑了CL量子产率和水解的敏感性）对氧化过程中去除的实体腔体积的依赖，形成了合理设计化学发光的便捷框架10 -甲基-9-（苯氧羰基）ac阳离子。
• N-alkylacridan carboxyl derivatives useful for chemiluminescent detection
  申请人：Lumigen, Inc.

  公开号：US05491072A1

  公开（公告）日：1996-02-13

  N-alkylacridan carboxylic acid derivative compounds (I) are used to generate chemiluminescence by the action of a peroxidase enzyme and an oxidant. The compounds I are useful in assays of all types.

  N-烷基吖啶羧酸衍生物化合物（I）通过过氧化物酶酶和氧化剂的作用产生化学发光。这些化合物I在各种类型的测定中都很有用。
• Vibrational spectra of phenyl acridine-9-carboxylates and their 10-methylated cations: A theoretical and experimental study
  作者：B. Zadykowicz、A. Ożóg、K. Krzymiński

  DOI：10.1016/j.saa.2010.02.014

  日期：2010.5

  Infrared spectra of phenyl acridine-9-carboxylates and their 10-methylated cationic derivatives were recorded and discussed. Experimental data were compared with theoretically predicted transitions at the DFT level of theory (using the B3LYP functional and 6-31G** basis set) for optimized geometries of molecules. Substitution influences the values of the wavenumbers of characteristic stretching and

  记录并讨论了a啶-9-羧酸苯酯及其10-甲基化阳离子衍生物的红外光谱。实验数据与DFT理论水平上的理论预测跃迁（使用B3LYP功能和6-31G **基集）进行了比较，以优化分子的几何形状。取代影响特征拉伸和弯曲模式的波数值，即对应于酯基和含有杂环氮原子的分子片段的波数。所选原子组的实验确定的跃迁与理论预测值密切相关。还讨论了化合物理论上衍生的某些理化特征与所选谱带的红外频率之间的相互依赖性。

表征谱图