2-氯-5-硝基苯甲酸乙酯 | 16588-17-3

• 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: 2-氯-5-硝基苯甲酸乙酯
• 英文名称: ethyl 2-chloro-5-nitrobenzoate
• 英文别名: 2-chloro-5-nitro-benzoic acid ethyl ester
• CAS: 16588-17-3
• 化学式: C₉H₈ClNO₄
• mdl: MFCD00115803
• 分子量: 229.62
• InChiKey: JXOMCDVAPASMML-UHFFFAOYSA-N

物化性质

• 沸点：
  329.5±22.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2916399090
• 安全说明：
  S26,S37/39
• 储存条件：
  存储在室温下

SDS

Name:	Ethyl 2-chloro-5-nitrobenzoate 90+% Material Safety Data Sheet
Synonym:
CAS:	16588-17-3

Section 1 - Chemical Product MSDS Name:Ethyl 2-chloro-5-nitrobenzoate 90+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16588-17-3	Ethyl 2-chloro-5-nitrobenzoate	90+%	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.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 16588-17-3: Personal Protective Equipment Eyes: Not available.
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: Not available.
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: C9H8ClNO4
Molecular Weight: 229.62

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16588-17-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-chloro-5-nitrobenzoate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 16588-17-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16588-17-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16588-17-3 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：

  2-氯-5-硝基苯甲酸乙酯 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 96.0h， 生成 5-amino-2-morpholin-4-yl-benzoic acid ethyl ester
  参考文献：
  名称：

  NOVEL 4,6-DISUBSTITUTED AMINOPYRIMIDINE DERIVATIVES HAVING BOTH AROMATIC AND HALOGENIC SUBSTITUENTS

  摘要：

  某些具有芳香族和卤素取代基的4,6-二取代氨基嘧啶衍生物。

  公开号：

  US20140057911A1
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 硫酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-氯-5-硝基苯甲酸乙酯
  参考文献：
  名称：

  PPAR-&ggr; modulators

  摘要：

  PPAR&ggr;活性调节剂提供了，这些调节剂在制药组合物和治疗类型II糖尿病和肥胖等疾病的方法中很有用。

  公开号：

  US06200995B1

文献信息

• Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium
  作者：F.D. Bellamy、K. Ou

  DOI：10.1016/s0040-4039(01)80041-1

  日期：1984.1

  Aromatic nitro compounds are readily reduced by SnCl2, 2 H2O in alcohol or ethyl acetate or by anhydrous SnCl2 in alcohol where other reducible or acid sensitive groups such as aldehyde, ketone, ester, cyano, halogen and O-benzyl remain unaffected.

  醇或乙酸乙酯中的SnCl 2，2 H 2 O或醇中的无水SnCl 2可以很容易地还原芳香硝基化合物，而醛，酮，酯，氰基，卤素和O-苄基等其他可还原或酸敏感基团则不受影响。
• Inhibitory growth evaluation and apoptosis induction in MCF-7 cancer cells by new 5-aryl-2-butylthio-1,3,4-oxadiazole derivatives
  作者：Rashmin Khanam、Kamal Ahmad、Iram I. Hejazi、Ibrar A. Siddique、Vikash Kumar、Abdul Roouf Bhat、Amir Azam、Fareeda Athar

  DOI：10.1007/s00280-017-3414-6

  日期：2017.11

  regulation of apoptotic signaling pathways may lead to cancer formation. Subsequently, the synthesis of effective chemotherapeutic agents that can induce apoptosis in tumor cell has emerged as a significant approach in cancer drug discovery. METHODS The goal of this work is to develop a potential antitumor agent exerting significant inhibitory effects on cancer cell and low cytotoxicity, for which we focused

  背景技术癌症已经成为全球健康问题之一，并且它是威胁生命的疾病，其特征在于细胞不受限制地生长。尽管化学疗法的管理取得了各种进步，但是由于高毒性，副作用和发展的耐药性，目前的抗癌药物如阿霉素，天冬酰胺酶，甲氨蝶呤，长春新碱的使用仍然受到限制。凋亡是关键的细胞过程，凋亡信号通路的调控不当可能导致癌症形成。随后，可以在肿瘤细胞中诱导凋亡的有效化学治疗剂的合成已成为癌症药物发现中的重要方法。方法这项工作的目的是开发一种潜在的抗肿瘤药物，该药物对癌细胞具有显着的抑制作用，且细胞毒性低，为此，我们将重点放在1,3,4-恶二唑的结构特征上，因为它是现代药物化学中的优先支架，并具有抑制可能与实现细胞永生和致癌作用有关的生长因子，酶和激酶的能力。结果体外MTT筛选试验显示化合物5-氨基苯基-2-丁基硫代-1,3,4-恶二唑（5e）对MCF-7癌细胞表现出最高的抑制作用，IC50值为10.05±1.08 µM，
• Design, synthesis, and anti-proliferative evaluation of new quinazolin-4(3H)-ones as potential VEGFR-2 inhibitors
  作者：Khaled El-Adl、Abdel-Ghany A. El-Helby、Rezk R. Ayyad、Hazem A. Mahdy、Mohamed M. Khalifa、Hamdy A. Elnagar、Ahmed B.M. Mehany、Ahmed M. Metwaly、Mostafa A. Elhendawy、Mohamed M. Radwan、Mahmoud A. ElSohly、Ibrahim H. Eissa

  DOI：10.1016/j.bmc.2020.115872

  日期：2021.1

  Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of cancer. Thus, nineteen new quinazoline-4(3H)-one derivatives were designed and synthesized. Preliminary cytotoxicity studies of the synthesized compounds were evaluated against three human cancer cell lines (HepG-2, MCF-7 and HCT-116) using MTT assay method. Doxorubicin and sorafenib were used as positive controls. Five compounds

  抑制 VEGFR-2 已被确立为治疗癌症的治疗策略。因此，设计并合成了19 种新的喹唑啉-4(3 H )-one 衍生物。使用 MTT 分析方法对合成的化合物对三种人类癌细胞系（HepG-2、MCF-7 和 HCT-116）的初步细胞毒性研究进行了评估。多柔比星和索拉非尼用作阳性对照。发现五种化合物对所有细胞系都具有良好的细胞毒活性。化合物16 f含有一个 2-氯-5-硝基苯基，已成为最活跃的成员。它对 HepG2、HCT-116 和 MCF-7 细胞的活性分别比阿霉素高约 4.39、5.73 和 1.96 倍，比索拉非尼高 3.88、5.59 和 1.84 倍。最活跃的细胞毒性剂在体外进一步评估了它们的 VEGFR-2 抑制活性。体外VEGFR-2 抑制的结果与细胞毒性数据的结果一致。此外，这些化合物与激酶结构域的分子对接支持了结果。
• Discovery of new quinazolin-4(3H)-ones as VEGFR-2 inhibitors: Design, synthesis, and anti-proliferative evaluation
  作者：Ibrahim H. Eissa、Abdel-Ghany A. El-Helby、Hazem A. Mahdy、Mohamed M. Khalifa、Hamdy A. Elnagar、Ahmed B.M. Mehany、Ahmed M. Metwaly、Mostafa A. Elhendawy、Mohamed M. Radwan、Mahmoud A. ElSohly、Khaled El-Adl

  DOI：10.1016/j.bioorg.2020.104380

  日期：2020.12

  reference drug, sorafenib (IC50 = 0.588 ± 0.06 µM). Furthermore, docking study was performed in order to understand the binding pattern of the new compounds into VEGFR-2 active site. Docking results attributed the potent VEGFR-2 inhibitory effect of the new compounds as they bound to the key amino acids in the active site, Glu883 and Asp1044, as well as their hydrophobic interaction with the receptor

  为了提高所设计化合物对受体活性位点的结合亲和力，通过对VEGFR-2报道的抑制剂7的修饰，设计并合成了十六种基于喹唑啉的新型衍生物。评价设计的化合物的VEGFR-2抑制作用。已经建立了抑制VEGFR-2作为治疗癌症的治疗策略。新化合物对HepG-2，MCF-7和HCT-116细胞系具有生物活性。阿霉素和索拉非尼用作阳性对照。 与参考药物阿霉素（IC 50）相比，观察到化合物18 d具有有希望的细胞毒活性（IC 50 = 3.74±0.14、5.00±0.20和6.77±0.27 µM）。 = 8.28、9.63和7.67 µM）和索拉非尼（IC 50  = 7.31、9.40和7.21 µM）。测试了活性最高的化合物的体外VEGFR-2抑制活性。VEGFR-2抑制的结果与细胞毒性数据一致。因此，化合物18 d的VEGFR-2抑制活性（IC 50  = 0.340±0.04 µM）优于参考药物索拉非尼（IC
• Benzoyl-piperazine derivatives
  申请人：Jolidon J. Synese

  公开号：US20050209241A1

  公开（公告）日：2005-09-22

  The invention relates to compounds of formula wherein the substituents are described herein. The compounds may be used in the treatment of illnesses based on the glycine uptake inhibitor, such as psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

  本发明涉及具有以下通式的化合物 其中取代基如本文所述。这些化合物可用于治疗基于抑制甘氨酸摄取的疾病，如精神疾病、疼痛、记忆和学习方面的神经退行性功能障碍、精神分裂症、痴呆症以及认知过程受损的其他疾病，例如注意力缺陷障碍或阿尔茨海默病。