2-羟基-5-硝基苯甲酸甲酯 | 17302-46-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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-羟基-5-硝基苯甲酸甲酯
• 中文别名: 5-硝基水杨酸甲酸甲酯；5-硝基水杨酸甲酯
• 英文名称: Methyl 2-hydroxy-5-nitrobenzoate
• 英文别名: methyl 5-nitrosalicylate
• CAS: 17302-46-4
• 化学式: C₈H₇NO₅
• mdl: MFCD00024695
• 分子量: 197.147
• InChiKey: UUBFELFUKFJSRD-UHFFFAOYSA-N

物化性质

• 熔点：
  114-117°C
• 沸点：
  328.7±27.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DCM、甲醇
• 稳定性/保质期：
  常温常压下稳定，避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2918290000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下应密闭避光保存，并置于通风、干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Methyl 5-nitrosalicylate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Methyl 5-nitrosalicylate
Ingredient name:
CAS number: 17302-46-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H7NO5
Molecular weight: 197.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2-羟基-5-硝基苯甲酸甲酯是一种有机中间体和医药中间体，可用于实验室研发过程和化工生产中。它可由水杨酸硝化后酯化得到，或直接由柳酸甲酯硝化得到。

制备

1. 反应步骤a：

   • 将20 g (145 mmol) 水杨酸置于250 mL的三口圆底烧瓶中。
   • 加入120 mL乙酸，加热至50℃溶解，并回流搅拌。
   • 慢慢滴加10 mL浓硝酸（约6分钟），继续加热并搅拌。使用TLC检测反应，约3小时后反应完全。
   • 将反应液趁热倒入冰水中，析出大量棕色固体，静置一段时间后抽滤，并用冰水洗涤滤饼，得到棕黄色固体2-羟基-5-硝基苯甲酸。
   • 将滤液放置在0℃继续析出固体，再一次抽滤。所得固体烘至恒重为15.92 g，收率为60%，备用。

2. 反应步骤b：

   • 将上述所得产物15.92 g (87 mmol) 2-羟基-5-硝基苯甲酸置于250 mL的三口圆底烧瓶中。
   • 加入150 mL甲醇，加热至70℃溶解，并回流搅拌。
   • 向反应液中滴加10 mL浓硫酸。反应1天后，使用TLC检测反应完全。
   • 将反应液趁热倒入冰水中，有固体析出。静置一段时间后抽滤，并用冰水洗涤滤饼，得到白色固体2-羟基-5-硝基苯甲酸甲酯。
   • 将滤液放置在0℃继续析出固体，再一次抽滤。所得固体烘至恒重，纯品质量为10.28 g，收率为60%。

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
  5-硝基水杨酸	5-Nitrosalicylic acid	96-97-9	C7H5NO5	183.12
  5-氨基水杨酸甲酯	methyl 5-amino-2-hydroxybenzoate	42753-75-3	C8H9NO3	167.164
  3-硝基苯甲酸甲酯	methyl 3-nitrobenzoate	618-95-1	C8H7NO4	181.148
  5-硝基水杨醛	5-Nitrosalicylaldehyde	97-51-8	C7H5NO4	167.121
  3-羟基-5-硝基苯甲酸	3-hydroxy-5-nitrobenzoic acid	78238-14-9	C7H5NO5	183.12
  5-氨基水杨酸	5-Aminosalicylic Acid	89-57-6	C7H7NO3	153.137
  2-羟基-5-硝基苯甲酰氯	5-nitrosalicyloyl chloride	3223-20-9	C7H4ClNO4	201.566
  水杨酸甲酯	methyl salicylate	119-36-8	C8H8O3	152.15

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-硝基水杨酸	5-Nitrosalicylic acid	96-97-9	C7H5NO5	183.12
  2-甲氧基-5-硝基苯甲酸甲酯	methyl 2-methoxy-5-nitrobenzoate	34841-11-7	C9H9NO5	211.174
  2-乙氧基-5-硝基苯甲酸甲酯	2-ethoxy-5-nitrobenzoic acid methyl ester	80074-34-6	C10H11NO5	225.201
  ——	2-difluoromethoxy-5-nitro-benzoic acid methyl ester	632626-83-6	C9H7F2NO5	247.155
  ——	methyl 2-isopropoxy-5-nitrobenzoate	176532-04-0	C11H13NO5	239.228
  2-甲氧基-5-硝基苯甲酸	2-methoxy-5-nitrobenzoic acid	40751-89-1	C8H7NO5	197.147
  ——	methyl 5-nitro-2-propoxybenzoate	1337569-70-6	C11H13NO5	239.228
  ——	2-allyloxy-5-nitro-benzoic acid methyl ester	1161799-78-5	C11H11NO5	237.212
  5-硝基-2-苯基甲氧基苯甲酸甲酯	2-benzyloxy-5-nitro-benzoic acid methyl ester	508211-52-7	C15H13NO5	287.272
  ——	Methyl 5-nitro-2-pentoxybenzoate	627541-12-2	C13H17NO5	267.282

反应信息

• 作为反应物：
  描述：

  2-羟基-5-硝基苯甲酸甲酯 在 sodium tetrahydroborate 、 nickel chloride hexahydrate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 2-ethoxy-5-nitrobenzoic acid
  参考文献：
  名称：

  通过与C位点相互作用的修饰，发现对TC-PTP具有选择性的新型高效和细胞活性ADC型PTP1B抑制剂

  摘要：

  PTP1B作为胰岛素信号的关键负调节剂，是2型糖尿病和肥胖症的新靶标。通过分子对接辅助设计修饰N- {4-[（3-苯基-脲基）-甲基]-苯基}-甲烷磺酰胺模板的B环，使其与PTP1B C位的残基Arg47和Lys41相互作用。发现一系列新型的PTP1B高效抑制剂。与PTP1B的C位点相互作用的结构活性关系已得到很好的说明。化合物8和18被证明是高效，最有前途的PTP1B抑制剂，与高度同源的TCPTP和其他PTP相比，具有细胞活性和极大的选择性。

  DOI：

  10.1016/j.ejmech.2017.12.064
• 作为产物：
  描述：

  水杨酸甲酯 在 copper(II) nitrate trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到2-羟基-5-硝基苯甲酸甲酯
  参考文献：
  名称：

  一种在温和条件下区域选择性单硝化苯酚的实用方法

  摘要：

  Cu(NO 3)2.3H 2O 被证明是一种高效、区域选择性和廉价的硝化试剂，用于合成单硝基取代的酚类化合物。检查了 12 个不同酚类的例子。已经实现了良好的产率 (67-90%)。

  DOI：

  10.3998/ark.5550190.p008.587

文献信息

• [EN] PYRROLE COMPOUNDS FOR THE TREATMENT OF PROSTAGLANDIN MEDIATED DISEASES<br/>[FR] COMPOSES PYRROLIQUES DESTINES AU TRAITEMENT DE MALADIES INDUITES PAR PROSTAGLANDINE
  申请人：GLAXO GROUP LTD

  公开号：WO2003101959A1

  公开（公告）日：2003-12-11

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein A, R1, R2a, R2b, Rx, R8, and R9 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine, in particular their use in the treatment of prostaglandin mediated diseases such as pain, inflammatory, immunological, bone, neurodegenerative or renal disorder.

  式(I)的化合物或其药学上可接受的衍生物：其中A、R1、R2a、R2b、Rx、R8和R9如规范中所定义，一种制备这种化合物的方法，包括这种化合物的药物组合物以及这种化合物在医学中的用途，特别是它们在治疗前列腺素介导的疾病，如疼痛、炎症、免疫、骨骼、神经退行性或肾脏疾病中的用途。
• Efficient Room-Temperature Synthesis and Antimicrobial Study of Novel 2-Aroylbenzofuran-3-ols from Substituted Methyl Salicylates and Phenacyl Bromides
  作者：Rashmi S. Kulkarni、Suresha Kumara T. Hanumanthappa、Nagendrappa Gopalpur、Sowmya H. B. Vijaya Kumar、Sunil S. More

  DOI：10.1080/00397911.2013.804932

  日期：2014.2

  Abstract The article describes a convenient and efficient synthetic route for the construction of 2-aroylbenzofuran-3-ols from readily available diverse methyl salicylates and phenacyl bromides using K2CO3 as catalyst in dimethylformamide as solvent at room temperature. The reaction involves two steps, which occur in quick succession within 1 h to deliver the product with reasonably high yields. All

  摘要 本文描述了一种方便有效的合成路线，用于在室温下以二甲基甲酰胺为溶剂，以 K2CO3 为催化剂，从易得的各种水杨酸甲酯和苯甲酰溴化物中构建 2-芳酰基苯并呋喃-3-醇。该反应包括两个步骤，在 1 小时内快速连续发生，以相当高的收率提供产品。所有合成的 2-芳酰基苯并呋喃-3-醇 (4a-u) 都进行了抗菌研究，其中一些已显示出显着的活性。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Oxidative cyclization of alkenoic acids promoted by AgOAc
  作者：Ulises A. Carrillo-Arcos、Jonathan Rojas-Ocampo、Susana Porcel

  DOI：10.1039/c5dt03808a

  日期：——

  Alkenoic acids derived from salicylic acid analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones.

  从水杨酸类似物中衍生的烯酸经过AgOAc触发的意外氧化环化过程，导致4H-苯并[1,3]二噁烷-4-酮的形成。
• [EN] MODIFIED PROTEINS AND PROTEIN DEGRADERS<br/>[FR] PROTÉINES MODIFIÉES ET AGENTS DE DÉGRADATION DE PROTÉINES
  申请人：CULLGEN SHANGHAI INC

  公开号：WO2021239117A1

  公开（公告）日：2021-12-02

  Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

  本文提供了结合或降解靶蛋白的化合物、药物组合物和方法。本文还提供了具有DNA损伤结合蛋白1（DDB1）结合基团的化合物。其中一些实施例包括连接物。其中一些实施例包括靶蛋白结合基团。本文还提供了配体-DDB1复合物。本文还提供了体内修饰的DDB1蛋白。
• Bicyclic-Fused Heteroaryl or Aryl Compounds
  申请人：Pfizer Inc.

  公开号：US20150284405A1

  公开（公告）日：2015-10-08

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物的异构体和药学上可接受的盐已被披露，其中所述化合物具有如规范中定义的Ia式结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。