噻吩-2,3-二羧酸 | 1451-95-2

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 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: 噻吩-2,3-二羧酸
• 中文别名: 2-噻唑异氰酸酯；噻吩-2,3-二甲酸
• 英文名称: thiophene-2,3-dicarboxylic acid
• 英文别名: Thiophen-2,3-dicarbonsaeure；2,3-thiophenedicarboxylic acid
• CAS: 1451-95-2
• 化学式: C₆H₄O₄S
• mdl: MFCD00034738
• 分子量: 172.161
• InChiKey: HIHKYDVSWLFRAY-UHFFFAOYSA-N

物化性质

• 保留指数：
  1618

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 储存条件：
  室温、密闭保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Thiophene-2,3-dicarboxylic acid
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: Thiophene-2,3-dicarboxylic acid
CAS number: 1451-95-2

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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: C6H4O4S
Molecular weight: 172.2

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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, 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：

  噻吩-2,3-二羧酸 在 硫酸 吡啶 、 肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 4,7-二氯噻吩并[2,3-d]吡嗪
  参考文献：
  名称：

  Substituted pyridines and pyridazines with angiogenesis inhibiting activity

  摘要：

  具有抑制血管生成活性的取代吡啶并呈现广义结构式的物质，其中包含A、B、D、E和L的环为苯或含氮杂环；基团X和Y可以是多种定义的连接单元中的任意一种；R1和R2可以是定义独立取代基，或者一起可以是环定义的桥；环J可以是芳基、吡啶基或环烷基基团；G基团可以是多种定义的取代基之一。还公开了含有这些物质的药物组合物，以及使用这些物质治疗具有异常血管生成或高渗透性过程特征的哺乳动物的方法。

  公开号：

  US06689883B1
• 作为产物：
  描述：

  3-甲基-4-氧代戊酸 在 potassium permanganate 、 diphosphorus trisulfide 作用下， 生成 噻吩-2,3-二羧酸
  参考文献：
  名称：

  Gruenewald, Chemische Berichte, 1887, vol. 20, p. 2586

  摘要：

  DOI：

文献信息

• Thermolysis of thiophenedicarboxylic acid anhydrides as a route to five-membered hetarynes
  作者：Manfred G. Reinecke、James G. Newsom、Lao-Jer Chen

  DOI：10.1021/ja00400a046

  日期：1981.5

  Diels-Alder adduct of the diene traps and the aryne 2,3-didehydrothiophene (8). A similar rationale explains the formation of dibenzothiophene from 7 and thiophene, the four monomethylthianaphthenes 22-25 from 5 and cyclopentadiene, 5,6-dimethylthianaphthene (150 from 5 and 2,3-dimethylbutadiene, and a mixture of hydroxythianaphthenes ( 1 9 ) from 5 and furan. The latter reaction also produces a mixture

  在噻吩的存在下，噻吩-2,3(5) 和 -3,4-二羧酸 (6) 和噻吩-2,3-二羧酸 (7) 的酸酐的流动真空热解 (FVT)，1, 3-环己二烯或苯得到噻吩 (Ma)，推测是通过二烯捕集器的中间体 Diels-Alder 加合物和芳炔 2,3-二脱氢噻吩 (8) 的芳构化作用产生的。类似的原理解释了由 7 和噻吩形成的二苯并噻吩、来自 5 的四种单甲基噻吩 22-25 和环戊二烯、5,6-二甲基噻吩（来自 5 和 2,3-二甲基丁二烯的 150，以及来自 1 9 的羟基噻吩的混合物） 5 和呋喃。后一反应也产生异构环戊烯噻吩 (19) 的混合物，这可能是由 15d 的脱羰产生的。5 与丙炔作为陷阱的 FVT 反应得到了丙炔基 (28) 和丙炔基噻吩 29 的混合物，这可能是由陷阱和芳炔 8 的烯反应产生的。酸酐 5 和 6 在熔融蒽中的分解仅导致弗里德尔- 工艺产品，例如来自 5 和
• Hydrothermal Synthesis and Crystal Structure of bis-[4-{(E)-2-(Pyridin-4-yl)vinyl}pyridine] Manganese(II) Thiophene-2,3-dicarboxylate
  作者：M. Zhu、Q.X. Cheng

  DOI：10.14233/ajchem.2015.17161

  日期：——

  One new manganese compound Mn(OAc)2·4H2O with thiophene-2,3-dicarboxylic acid and bpp [4-(E)-2-(pyridin-4-yl)vinyl}pyridine] has been successfully synthesized. Compound shows a one-dimensional framework. The 3D supramolecular structure is formed via hydrogen bonding formation.

  一种新型锰化合物Mn(OAc)2·4H2O与噻吩-2,3-二羧酸及bpp[4-(E)-2-(吡啶-4-基)乙烯基}吡啶]已成功合成。该化合物展示出一维框架结构。通过氢键形成，构建了三维超分子结构。
• LUMINESCENT SQUARAINE ROTAXANE COMPOUNDS
  申请人：SETA BioMedicals, LLC

  公开号：US20190048196A1

  公开（公告）日：2019-02-14

  Luminescent reporter compounds that are rotaxanes having the structure where B—Z—C is a reporter molecule based on a squaraine type molecule, or similar reporter, and K is a macrocycle that encircles and interlocks with the reporter molecule. Applications of the reporter compounds are provided, as well as reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing the reporter compounds.

  具有如下结构的发光报告化合物，是一种轮烷： 其中B—Z—C是基于方酸染料类型分子或类似报告分子的报告分子，K是一个环绕并与报告分子互锁的大环。报告化合物的应用被提供，以及用于合成报告化合物的反应中间体，以及合成报告化合物的方法。
• Aromatic dicarboxamides
  申请人：Ciba-Geigy Corporation

  公开号：US04025505A1

  公开（公告）日：1977-05-24

  N-(4-aminophenyl)-aromatic dicarboximides, e.g. those of the formula ##STR1## OR SALTS THEREOF ARE ANTICONVULSANTS.

  N-(4-氨基苯基)-芳香二羧酰亚胺，例如式##STR1##的化合物或其盐是抗癫痫药物。
• Thiophene bioisosteres of GluN2B selective NMDA receptor antagonists: Synthesis and pharmacological evaluation of [7]annuleno[b]thiophen-6-amines
  作者：Sören Baumeister、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.bmc.2019.115245

  日期：2020.1

  Br-atom or a hydroxymethyl moiety in 2-position were less tolerated by the GluN2B receptor. Very similar relationships between the structure and GluN2B affinity and structure and σ affinity, in particular σ2 affinity, were detected. A slight preference for the ifenprodil binding site of GluN2B receptors over σ1 and σ2 receptors was found for methylamines 11c (≈2-fold) and 11d (≈1.5-2-fold) as well as for

  制备了强效的GluN2B受体阴性变构调节剂的噻吩生物同工异构体，并进行了药理学评估。在第一步反应中，通过噻吩-3-羧酸（8）的羧化反应，大大改善了4,5,7,8-四氢[7]环核[b]噻吩-6-（10）的五步合成。还原胺化和烷基化产生了三个同源系列的仲和叔苯基烷基胺5、11和12。金属化，与1-甲酰基哌啶反应并随后还原得到了羟甲基衍生物15和16，它们被设计为苯酚的生物等排体。通过用NBS溴化酮10并随后进行还原性胺化反应，获得了2-溴衍生物18。使用带有3-苯基丙基氨基或4-苯基丁基氨基部分的[7]环戊[b]噻吩实现了高GluN2B亲和力（例如5c：Ki = 5.9 nM；11d：Ki ＝ 9.0nM）。叔乙胺12显示出比叔甲胺11或仲胺5低的GluN2B亲和力（例如5c：Ki = 5.9 nM; 11c：Ki = 6.0; 12c：Ki = 51 nM）。GluN2B受体对2位的Br原子