9-吖啶羧酸 | 5336-90-3

• 物质功能分类: 生物化工 - 生化试剂
• 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: 9-吖啶羧酸
• 中文别名: 9-羧基吖啶；9-吖啶甲酸
• 英文名称: acridine-9-carboxylic acid
• 英文别名: 9-acridinecarboxylic acid；9-carboxyacridine
• CAS: 5336-90-3
• 化学式: C₁₄H₉NO₂
• mdl: MFCD00009734
• 分子量: 223.231
• InChiKey: IYRYQBAAHMBIFT-UHFFFAOYSA-N

物化性质

• 熔点：
  290 °C (dec.)(lit.)
• 沸点：
  480.4±18.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（非常轻微，超声处理）、碱水溶液（轻微）、DMSO（轻微
• 稳定性/保质期：

  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

Name:	Acridine-9-Carboxylic Acid Hydrate Material Safety Data Sheet
Synonym:	None known
CAS:	5336-90-3

Section 1 - Chemical Product MSDS Name:Acridine-9-Carboxylic Acid Hydrate Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5336-90-3	Acridine-9-Carboxylic Acid Hydrate	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. May cause chemical conjunctivitis.
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. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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:
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.

---

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.

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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# 5336-90-3: 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: 290 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: Negligible.
Specific Gravity/Density:
Molecular Formula: C14H9NO2
Molecular Weight: 223.23

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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:
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# 5336-90-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Acridine-9-Carboxylic Acid Hydrate - 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# 5336-90-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5336-90-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5336-90-3 is not on the TSCA Inventory because it is a hydrate.
It is considered to be listed if the CAS number for the anhydrous form
is on the inventory (40CFR720.3(u)(2)).

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

吖啶及其盐类的稀溶液呈紫色或绿色荧光，而盐类的稀溶液则主要呈现绿色荧光。当溶液被进一步稀释时，因盐水解作用，游离的吖啶会变成紫色荧光。吖啶盐广泛应用于光催化剂和染料的制备，并且其衍生物常用于标记蛋白质、抗原、抗体以及核酸（包括DNA和RNA）等。

用途方面，吖啶及其盐类主要用作蛋白、抗原、抗体及核酸（DNA和RNA）等的有效标记工具。

反应信息

• 作为反应物：
  描述：

  9-吖啶羧酸 在 四甲基乙二胺 、 copper(II) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以93.5%的产率得到吖啶
  参考文献：
  名称：

  一种吖啶的制备方法

  摘要：

  本发明涉及一种吖啶的制备方法。该吖啶的制备方法包括以下步骤：将9‑羧基吖啶与催化剂、配体在有机溶剂中混合均匀，在140‑200℃反应1‑8h，即得；所述配体为N,N'‑二甲基哌嗪、三乙胺、邻菲罗啉、取代的邻菲罗啉、N,N,N',N'‑四甲基乙二胺、N,N‑二甲基苯胺、N,N‑二异丙基乙胺中的至少一种。本发明的吖啶的制备方法，以9‑羧基吖啶为原料一步合成吖啶，在催化剂和配体存在条件下进行反应，反应过程平缓易控，产品的纯度和收率高，显著降低了吖啶的工业制造成本，具有良好的工业应用价值。

  公开号：

  CN110003106B
• 作为产物：
  描述：

  9,10-dihydro-acridine-9-carbonitrile 在 硫酸 作用下， 生成 9-吖啶羧酸
  参考文献：
  名称：

  Lehmstedt; Wirth, Chemische Berichte, 1928, vol. 61, p. 2044

  摘要：

  DOI：

文献信息

• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20160218303A1

  公开（公告）日：2016-07-28

  A family of phosphorescent emitter compounds containing a carbene ligand L A selected from the group consisting of: is disclosed. These compounds enhance the performance of OLEDs when incorporated therein.

  揭示了一类含有从以下组中选择的卡宾配体L的磷光发射物化合物家族。这些化合物在其中加入后提高了OLED的性能。
• Synthesis and antiproliferative activity of novel symmetrical alkylthio- and alkylseleno-imidocarbamates
  作者：Elena Ibáñez、Daniel Plano、María Font、Alfonso Calvo、Celia Prior、Juan Antonio Palop、Carmen Sanmartín

  DOI：10.1016/j.ejmech.2010.11.013

  日期：2011.1

  in the five cell lines tested. Therefore, compounds 2b and 8b were evaluated by flow cytometric analysis for their effects on cell cycle distribution and apoptosis in MCF-7 cells. 2b was the most active, with an apoptogenic effect similar to camptothecin, which was used as a positive control. Both of them provoked cell cycle arrest leading to the accumulation of cells in either G2/M and S phase. These

  这里描述的研究涉及一系列三十种新的对称取代的亚氨基硫代氨基甲酸酯和亚氨基硒代氨基甲酸酯衍生物的合成及其在体外对五种人类肿瘤细胞系的抗肿瘤活性的评估：乳腺腺癌（MCF-7），结肠癌（HT- 29），淋巴细胞白血病（K-562），肝癌（Hep-G2），前列腺癌（PC-3）和一种非恶性乳腺衍生细胞系（MCF-10A）。在至少一种细胞系中，十八种化合物的GI 50值低于10μM。事实证明，两种癌细胞（MCF-7和HT-29）对5种化合物（1b，2b，3b，4b和5b）最敏感），其生长抑制在纳摩尔范围内，化合物1b，3b，7b，8b和9b的值小于1μM。此外，所有上述化合物均显示出较低的GI 50比一些标准的化学治疗药物的参考值高。结果还表明，在硒位置的脂族链的性质（甲基比苄基更好）和杂原子的性质（Se比S更好）对化合物的抗增殖活性有显着影响。这些发现加强了我们先前关于硒甲基作为此类化合物生物活性支
• 二核化配位子又は二核金属錯体
  申请人：学校法人同志社

  公开号：JP2021042188A

  公开（公告）日：2021-03-18

  【課題】簡易に合成でき的確な抗がん作用を有する二核金属錯体の提供。【解決手段】下記式（Ｉ）で示される二核化配位子、およびその二核金属錯体。(式中、Ｘは同一又は異なってＨ、Ｃｌ、ＯＭｅ、又は、Ｍｅであり、ＹはＨ、フェニル基、置換カルバモイル基等である。）【選択図】なし

  提供具有简便合成且具有确切抗癌作用的双核金属配合物。通过以下式（I）所示的双核配体以及其双核金属配合物。（在该式中，X代表相同或不同的H、Cl、OMe或Me，Y代表H、苯基、取代羰基等。）【选择图】无
• 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。

表征谱图