水杨酸对硝基苯酯 | 17374-48-0

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 水杨酸对硝基苯酯
• 中文别名: 对硝基苯基水杨酸酯；2-羟基苯甲酸-4-硝基苯酯；水杨酸4-硝基苯酯
• 英文名称: Salicylsaeure-4-nitrophenylester
• 英文别名: 4'-nitrophenyl salicylate；Salicylsaeure-<4-nitro-phenylester>；4-Nitrophenyl salicylate；(4-nitrophenyl) 2-hydroxybenzoate
• CAS: 17374-48-0
• 化学式: C₁₃H₉NO₅
• mdl: MFCD00059835
• 分子量: 259.218
• InChiKey: XSTIAAYONYIWGB-UHFFFAOYSA-N

物化性质

• 熔点：
  148°C
• 沸点：
  409.2±25.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  室温

SDS

4-Nitrophenyl Salicylate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Nitrophenyl Salicylate

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Nitrophenyl Salicylate
Percent: ....
CAS Number: 17374-48-0
Synonyms: Salicylic Acid 4-Nitrophenyl Ester
C13H9NO5
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
4-Nitrophenyl Salicylate

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Very pale yellow - Pale yellow
No data available
Odour:
4-Nitrophenyl Salicylate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:148°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Acetone

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
4-Nitrophenyl Salicylate

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：白色结晶，熔点为150.5-151.5℃。

用途：作为利胆酚的中间体。

生产方法：通过在三氯化磷参与下对硝基苯酚与水杨酸反应制得。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Acetylsalicylsaeure-4-nitrophenylester	77008-82-3	C15H11NO6	301.255

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  水杨酸-(4-氨基苯基酯)	salicylic acid-(4-amino-phenyl ester)	5003-49-6	C13H11NO3	229.235
  醋氨沙洛	acetaminosalol	118-57-0	C15H13NO4	271.273
  2-(4-硝基苯氧基)苯羧酸	o-carboxyphenyl p-nitrophenyl ether	6082-87-7	C13H9NO5	259.218

反应信息

• 作为反应物：
  描述：

  水杨酸对硝基苯酯 在 溶剂黄146 、 锌 作用下， 生成 醋氨沙洛
  参考文献：
  名称：

  ACETYLAMINOPHENYL SALICYLATE. THE PREPARATION OF SALOPHEN.

  摘要：

  DOI：

  10.1021/ja02240a017
• 作为产物：
  描述：

  Acetylsalicylsaeure-4-nitrophenylester 在 phosphate buffer 作用下， 以 1,4-二氧六环 为溶剂， 以87%的产率得到水杨酸对硝基苯酯
  参考文献：
  名称：

  Wagner; Hanfeld, Pharmazie, 1980, vol. 35, # 12, p. 739 - 741

  摘要：

  DOI：

文献信息

• Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions
  作者：Michael Black、J. I. G. Cadogan、Hamish McNab

  DOI：10.1039/c002480e

  日期：——

  Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650 °C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl

  在650℃下，对 2-（烯丙氧基）苯甲酸芳基酯5和相应的2-（烯丙硫基）苯甲酸芳基酯6进行快速真空热解（FVP），分别得到二苯并呋喃19和二苯并噻吩20。该机制涉及产生苯氧基 （或者 噻吩氧基）通过O-烯丙基（或小号烯丙基）键，然后在酯基上进行ipso攻击，CO 2损失和所得芳基自由基环化。综合而言，该方法对p-取代的底物效果很好，可产生2-取代的二苯并呋喃19b-f（73-90％）和二苯并噻吩20b-c（90-94％）。在m-取代的底物的环化以及自由基与取代基和ipso-攻击的竞争性相互作用中，几乎没有选择性显示出o取代的底物的热解复杂化。相关自由基前体的FVP包括2-（烯丙氧基）苯基苯甲酸酯43没有产生二苯并呋喃，而2-（烯丙氧基-5-甲基）偶氮苯 44降低了产量。通过FVP不能获得咔唑2-（烯丙基氨基）苯甲酸4-甲基苯酯 42。
• Synthesis of salicylates from anionically activated aromatic trifluoromethyl group
  作者：Huilin Xie、Chuankai Lin、Ruixiang Wang、Jin-Biao Liu

  DOI：10.1016/j.tetlet.2021.153592

  日期：2022.1

  An efficient approach to salicylates via a novel transformation of anionically activated aromatic trifluoromethyl group is described. Anionically activated trifluoromethyl group can react with phenols/alcohols under alkaline conditions to afford aryl/alkyl salicylates in high yields. Mechanism studies indicate that the carbonyl oxygen atom of ester is from the H2O in the solvent.

  描述了一种通过阴离子活化芳族三氟甲基的新转化来制备水杨酸盐的有效方法。阴离子活化的三氟甲基基团可以在碱性条件下与酚/醇反应，以高收率得到芳基/烷基水杨酸酯。机理研究表明，酯的羰基氧原子来自溶剂中的H 2 O。
• Neue Methoden zur Herstellung von Carbonsäure-arylestern. Über aktivierte Ester VIII
  作者：B. Iselin、W. Rittel、P. Sieber、R. Schwyzer

  DOI：10.1002/hlca.19570400216

  日期：——

  Two new methods for preparing carboxylic acid aryl esters are presented. They consist in reacting the carboxylic acid with (a) aryl sulfites or (b) aryl phosphites in the presence of pyridine. A possible mechanism of the sulfite method is discussed.

  提出了两种制备羧酸芳基酯的新方法。它们在于使羧酸与（a）亚硫酸芳基酯或（b）亚磷酸芳基酯在吡啶存在下反应。讨论了亚硫酸盐法的可能机理。
• An efficient approach for the synthesis of 1,2-dihydroxanthones enabled by one-pot Claisen condensation/cyclization reactions
  作者：Huaimo Wu、Song Liu、Youyi Wang、Man Yuan、Hong Zhang、Hua Zhou、Lianbo Xiao、Changwu Zheng、Hongxi Xu

  DOI：10.1039/d1ob00470k

  日期：——

  of natural products and useful building blocks in organic synthesis. So far, they have been less studied. In this report, a mild, efficient and green method for the synthesis of 1,2-dihydroxanthones has been developed in one pot through Claisen condensation and O-cyclization under waste-induced relay catalysis with minimum organic solvents. The by-product (HMDS or NH3·H2O) of the first step turned

  1,2-二氢氧杂蒽酮 (DHX) 是天然产物的核心结构，也是有机合成中有用的组成部分。到目前为止，它们的研究较少。在本报告中，通过克莱森缩合和O-环化，在废物诱导的中继催化下，在最少有机溶剂的情况下，开发了一种温和、高效、绿色的 1,2-二羟基蒽酮合成方法。副产品（HMDS 或 NH 3 ·H 2第一步的 O) 被证明是第二步的促进剂，它可以在水性介质中有效地进行，而无需添加其他催化剂。使用水杨酸三氟乙酯的反应可以在温和的条件下进行，以确保以高产率生成易受攻击的 DHX。无论取代基类型及其在结构上的位置如何，底物范围都非常广泛。具体来说，DHX 的多功能性通过它们转化为氧杂蒽酮和其他复杂结构来证明。
• Effects of cyclodextrin on hydrolysis and the Smiles rearrangement of salicylic acid esters
  作者：A. K. Yatsimirsky、K. Yu. Bezsoudnova

  DOI：10.1007/bf01431107

  日期：1996.11

  the mechanism of hydrolysis: free ester in the deprotonated form undergoes hydrolysis through the mechanism of intramolecular general base catalysis, while the ester bound to cyclodextrin is hydrolyzed due to the nucleophilic attack of the deprotonated hydroxyl group of β-CD at a neutral substrate molecule. The effects of cyclodextrin on the rate constant of borate-catalyzed hydrolysis were interpreted

  研究了β-环糊精（β-CD）对水杨酸甲酯、对硝基苯酯和间硝基苯酯的“水性”水解以及对硝基苯水杨酸酯的Smiles重排的影响。没有观察到 β-CD 对甲酯“水性”水解的 pH 无关速率常数的影响，而 β-CD 加速了硝基苯酯的“水性”水解。10次​​。这些酯类进入β-CD的空腔，伴随着水解机制的变化：去质子化形式的游离酯通过分子内通用碱催化的机制发生水解，而与环糊精结合的酯由于水解作用而发生水解。 β-CD 的去质子化羟基对中性底物分子的亲核攻击。环糊精对硼酸盐催化水解速率常数的影响是通过假设与 β-CD 结合的底物在去质子化的环糊精羟基上经历硼酸盐辅助攻击来解释的。Smiles 重排是一种分子内亲核取代反应，在 β-CD 存在下会加速。