5-硝基-噻吩-2-甲酸甲酯 | 5832-01-9

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-硝基-噻吩-2-甲酸甲酯
• 中文别名: 5-硝基-2-噻吩甲酸甲酯；5-硝基噻吩-2-甲酸甲酯
• 英文名称: methyl 5-nitrothiophene-2-carboxylate
• 英文别名: 5-Nitro-thiophen-2-carbonsaeure-methylester；5-Nitro-thiophen-carbonsaeure-(2)-methylester；methyl 5-nitro-2-thiophenecarboxylate
• CAS: 5832-01-9
• 化学式: C₆H₅NO₄S
• mdl: MFCD02702303
• 分子量: 187.176
• InChiKey: ROZWUNOYMSUTKS-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  306.9±22.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  | 2～8℃ |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Nitrothiophene-2-carboxylic acid methyl ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Nitrothiophene-2-carboxylic acid methyl ester
CAS number: 5832-01-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H5NO4S
Molecular weight: 187.2

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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, sulfur 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

反应信息

• 作为反应物：
  描述：

  5-硝基-噻吩-2-甲酸甲酯 在 silver nitrate ammonium peroxydisulfate 、 硫酸 、 硝酸 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 4-methyl-3,5-dinitro-2-methoxycarbonylthiophen
  参考文献：
  名称：

  控制均质芳族取代中ipso攻击选择性的因素。烷基与硝基噻吩衍生物的反应

  摘要：

  为了阐明控制自由基加成到芳族底物上的位置选择性的因素，已经研究了接近电子中性的甲基和亲核的1-金刚烷基与某些选定的硝基噻吩衍生物的反应。在具有5-硝基-2-X-噻吩（II），（V）和（VI）和3,5-二硝基-2-甲氧基羰基噻吩（III）的情况下，金刚烷基仅产生ipso攻击的产物，而甲基在未取代的4-位上有选择地添加一个残基。另一方面，带有4-硝基-2-甲氧基-羰基噻吩（I）的两个基团和带有4-5-二硝基-2-甲氧基羰基噻吩（IV）的两个基团均得到ipso的产物。-通过从5-位取代硝基来进行-取代。通过假定加成步骤的过渡态的性质根据自由基的极性特征和芳族底物的电子缺乏而变化来解释这些位置选择性的变化。

  DOI：

  10.1039/p29800001331
• 作为产物：
  描述：

  5-硝基噻吩-2-甲醛 在 sodium hypochlorite 、 disodium hydrogenphosphate 、 硫酸 作用下， 以 水 为溶剂， 反应 50.0h， 生成 5-硝基-噻吩-2-甲酸甲酯
  参考文献：
  名称：

  理解聚酰胺对DNA小沟槽识别的化学病因

  摘要：

  由芳族氨基酸，即1-甲基-1 H-咪唑Im，1-甲基-1 H-吡咯Py和3-羟基-1 H-吡咯Hp组成的月牙形聚酰胺，以2：1和1：1配体/ DNA复合物的形式结合在DNA的小沟中。DNA序列特异性可归因于形状选择性识别以及每个杂环在小沟纹底面上的碱基对的边缘所呈现的唯一角或成对的角。在这里，我们研究了五元芳香族氨基酸家族的杂环结构与DNA序列特异性之间的关系。通过定量DNase-I足迹分析法，包含8种不同的芳香族氨基酸的聚酰胺的识别行为，即1-甲基-1 H-吡唑Pz，1 H-吡咯Nh，5-甲基噻唑Nt和4-甲基噻唑Th，将3-甲基噻吩Tn，噻吩Tp，3-羟基噻吩Ht和呋喃Fr与含有母环氨基酸Py，Im和Hp的聚酰胺进行了比较，以区分DNA中的四个WatsonCrick碱基对小沟。数据分析和分子建模表明，每个杂环固有的几何形状在聚酰胺区分DNA序列的能力中起着重要作用。结合似乎对聚酰胺和D

  DOI：

  10.1002/hlca.200290024

文献信息

• [EN] 6H-THIENO`2, 3-B!PYRROLE DERIVATIVES AS ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE (GNRH)<br/>[FR] DERIVES DE 6H-THIENO`2,3-B!PYRROLE EN TANT QU'ANTAGONISTES DE LA GONADOLIBERINE (GNRH)
  申请人：ASTRAZENECA AB

  公开号：WO2004018480A1

  公开（公告）日：2004-03-04

  The invention relates to a group of novel thieno-pyrrole compounds of Formula (I): wherein: R1, R2, R3, R4 and R5 are as defined in the specification, which are useful as gonadotrophin releasing hormone antagonists. The invention also relates to pharmaceutical formulations of said compounds, methods of treatment using said compounds and to processes for the preparation of said compounds.

  这项发明涉及一组新型噻吩-吡咯烷化合物的化学式（I）：其中：R1、R2、R3、R4和R5如规范中定义，这些化合物可用作促性腺激素释放激素拮抗剂。该发明还涉及所述化合物的药物配方、使用所述化合物的治疗方法以及所述化合物的制备方法。
• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• [EN] 5,8-DISUBSTITUTED-[1,2,4]TRIAZOLO[1,5-A]PYRIDINYL AND 5,8-DISUBSTITUTED-IMIDAZO[1,2-A]PYRIDINE DERIVATIVES USEFUL AS INHIBITORS OF ENTEROPEPTIDASE<br/>[FR] DÉRIVÉS DE [1,2,4]TRIAZOLO[1,5-A]PYRIDINYLE 5,8-DISUBSTITUÉS ET D'IMIDAZO[1,2-A]PYRIDINE 5,8-DISUBSTITUÉS UTILES EN TANT QU'INHIBITEURS DE L'ENTÉROPEPTIDASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021013742A1

  公开（公告）日：2021-01-28

  The present invention is directed to 5,8-disubstituted-[1,2,4]triazolo[1,5- a]pyridinyl and 5,8-disubstituted-imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the enteropeptidase enzyme.

  本发明涉及5,8-二取代-[1,2,4]三唑并[1,5-a]吡啶基和5,8-二取代咪唑并[1,2-a]吡啶衍生物，含有它们的药物组合物以及它们在治疗由肠肽酶调节的疾病和症状中的应用。
• Design, synthesis, and biological evaluation of 2-(phenoxyaryl)-3-urea derivatives as novel P2Y1 receptor antagonists
  作者：Jingjing Peng、Lifen Zhao、Lanlan Wang、Hui Chen、Yunguang Qiu、Jiang Wang、Huaiyu Yang、Jun Liu、Hong Liu

  DOI：10.1016/j.ejmech.2018.09.014

  日期：2018.10

  A novel series of 2-(phenoxyaryl)-3-urea derivatives were designed, synthesized, and biologically evaluated for their anti-thrombotic activity. Most of compounds exhibited good inhibition against P2Y1 receptor. Among them, three compounds 11, 12, and 13 demonstrated good P2Y1 receptor antagonistic potency in vitro (IC50 = 0.62 μM, 0.82 μM, and 0.21 μM, respectively). In antiplatelet aggregation study

  设计，合成了一系列新颖的2-（苯氧基芳基）-3-脲衍生物，并对它们的抗血栓形成活性进行了生物学评估。大多数化合物对P2Y 1受体表现出良好的抑制作用。其中，三种化合物11，12和13表现出良好的P2Y 1个受体拮抗效力的体外（IC 50  = 0.62μM，0.82μM，和0.21μM，分别地）。在抗血小板聚集研究中，四种化合物2，3，9，和13显示出良好的抗血小板活性。化合物与P2Y 1的可能结合方式还通过分子对接模拟探索了受体。对接研究表明，化合物13通过疏水相互作用与Phe119相互作用良好，并适度改善了P2Y 1受体的拮抗活性，使其有理由进一步研究。
• [EN] 3-ALKYLIDENEHYDRAZINO SUBSTITUTED HETEROARYL COMPOUNDS AS THROMBOPOIETIN RECEPTOR ACTIVATORS<br/>[FR] UTILISATION DE COMPOSES HETEROARYLES A SUBSTITUTION 3-ALKYLIDENEHYDRAZINO EN TANT QU'ACTIVATEURS DU RECEPTEUR DE LA THROMBOPOIETINE
  申请人：NISSAN CHEMICAL IND LTD

  公开号：WO2004108683A1

  公开（公告）日：2004-12-16

  A compound represented by the formula (1): wherein A is a nitrogen atom or CR4, B is an oxygen atom, a sulfur atom or NR9 (provided that when A is a nitrogen atom, B is not NH), R1 is a C2-14; aryl group, L1 is a bond, CR10R11, an oxygen atom, a sulfur atom or NR12, X is OR13, SR13 or NR14NR15, R2 is a hydrogen atom, a formyl group, a C1-10; alkyl group or the like, L2 is a bond or the like, L3 is a bond, CR17R18, an oxygen atom, a sulfur atom or NR19, L4 is a bond, CR20R21, an oxygen atom, a sulfur atom or NR22, Y is an oxygen atom, a sulfur atom or NR23, and R3 is a C2-14; aryl group, a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

  化合物的结构式（1）如下：其中A是氮原子或CR4，B是氧原子、硫原子或NR9（但当A是氮原子时，B不是NH），R1是C2-14芳基，L1是键，CR10R11、氧原子、硫原子或NR12，X是OR13、SR13或NR14NR15，R2是氢原子、甲酰基、C1-10烷基或类似物，L2是键或类似物，L3是键，CR17R18、氧原子、硫原子或NR19，L4是键，CR20R21、氧原子、硫原子或NR22，Y是氧原子、硫原子或NR23，R3是C2-14芳基、化合物的互变异构体、前药或药学上可接受的盐或其溶剂化合物。