5-苯基噻吩-2-羧酸 | 19163-24-7

• 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-苯基噻吩-2-羧酸
• 中文别名: 5-苯基-2-噻吩羧基酸；5-苯基-2-噻吩甲酸；5-苯基-2-噻吩羧基 酸
• 英文名称: 5-phenyl-2-thiophenecarboxylic acid
• 英文别名: 5-phenylthiophene-2-carboxylic acid；5-Phenyl-thiophen-2-carbonsaeure；2-Phenyl-thiophen-carbonsaeure-(5)
• CAS: 19163-24-7
• 化学式: C₁₁H₈O₂S
• mdl: MFCD01313432
• 分子量: 204.249
• InChiKey: QGMFBCDNJUZQBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  186-190°C
• 沸点：
  393.6±30.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)
• 最大波长(λmax)：
  310nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 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°C

SDS

Name:	5-Phenylthiophene-2-carboxylic acid 95+% Material Safety Data Sheet
Synonym:	None Known
CAS:	19163-24-7

Section 1 - Chemical Product MSDS Name:5-Phenylthiophene-2-carboxylic acid 95+% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19163-24-7	5-Phenylthiophene-2-carboxylic acid	95+%	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. May cause chemical conjunctivitis.
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:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 19163-24-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 186 - 190 deg C
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: C11H8O2S
Molecular Weight: 204

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 19163-24-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Phenylthiophene-2-carboxylic acid - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 19163-24-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19163-24-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19163-24-7 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

制备方法与用途

噻吩衍生物广泛应用于合成农药、医药、化学试剂、染料和高分子助剂等。其中，5-苯基噻吩-2-羧酸在有机合成中具有广泛的应用。

其制备方法如下：以5-溴噻吩-2-羧酸为原料、苯硼酸为硼试剂、K3PO4·7H2O为碱，在氯(2-二环己基膦基-2',4',6'-三异丙基-1,1'-联苯基)［2-(2'-氨基-1,1'-联苯)］钯(Ⅱ)(Xphos-Pd-G2)和2-二环己基磷-2',4',6'-三异丙基联苯(Xphos)体系的催化下，成功合成了5-苯基噻吩-2-羧酸。

反应信息

• 作为反应物：
  描述：

  5-苯基噻吩-2-羧酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 5-苯基-2-噻吩羰酰氯
  参考文献：
  名称：

  可再生松树树脂松香衍生物在农作物保护中的抗真菌应用

  摘要：

  在当前的工作中，我们从天然产物松香中合成了两个系列的脱氢松香酰胺衍生物，并评估了它们对Valsa mali，Phytophthora capsici，Botrytis cinerea，Sclerotiania sclerotiorum和Fusarium oxysporum的抗真菌作用。体外和体内抗真菌活性结果表明，含噻吩杂环的松香基酰胺化合物对灰葡萄孢的抑制作用更好。尤其是，化合物5b（5-氟-2-噻吩脱氢松香基酰胺）对EC的灰葡萄孢表现出优异的抗真菌性能。50为0.490 mg / L，低于阳性对照戊硫吡py（0.562 mg / L）。生理生化研究表明，化合物5b对灰葡萄孢的主要作用机制是改变菌丝体形态，增加细胞膜通透性，并抑制呼吸代谢中的TCA途径。此外，QSAR和SAR研究表明，松香类酰胺衍生物的电荷分布通过化合物与目标受体之间的氢键键合，结合和静电相互作用，在抗真菌活性中起着关键

  DOI：

  10.1021/acs.jafc.0c00562
• 作为产物：
  描述：

  2-碘-5-苯基噻吩 在 溴乙烷 、 乙醚 、 magnesium 作用下， 生成 5-苯基噻吩-2-羧酸
  参考文献：
  名称：

  Steinkopf; Gording, Biochemische Zeitschrift, 1937, vol. 292, p. 368

  摘要：

  DOI：

文献信息

• Inhibitors of cathepsin S
  申请人：IRM LLC

  公开号：US20040198780A1

  公开（公告）日：2004-10-07

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme (e.g., cathespin K). The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了用于选择性抑制蛋白酶S的化合物、组合物和方法。在一个优选方面，当至少存在另一种蛋白酶同工酶（例如，蛋白酶K）时，选择性地抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S来治疗受试者疾病状态的方法。
• Aqueous-Phase Chemistry of η³-Allylpalladium(II) Complexes with Sulfonated <i>N</i>-Heterocyclic Carbene Ligands: Solvent Effects in the Protolysis of Pd–C Bonds and Suzuki–Miyaura Reactions
  作者：Juan M. Asensio、Román Andrés、Pilar Gómez-Sal、Ernesto de Jesús

  DOI：10.1021/acs.organomet.7b00635

  日期：2017.11.13

  synthesis of water-soluble η3-allyl Pd(II) complexes containing sulfonated N-heterocyclic carbene (NHC) ligands of general formula [Pd(NHC)n(η3-allyl)Cl2–n] is reported (n = 1 (1) or 2 (8)). Monocarbene complexes were obtained with the most sterically hindered NHC ligands, and biscarbenes with the less sterically hindered NHCs. The behavior of the isolated complexes in water under acidic, neutral, or alkaline

  水溶性η的合成3含有磺化-烯丙基钯（II）络合物ñ -杂环卡宾（NHC）配体的通式[钯（NHC）Ñ（η 3 -烯丙基）氯-2- Ñ ]报道（Ñ = 1（1）或2（8））。获得了具有最受空间阻碍的NHC配体的单碳烯配合物，以及具有受较少位阻的NHC的双卡宾。已经研究了分离的配合物在酸性，中性或碱性条件下在水中的行为。该络合物在中性或碱性条件下在水中相当稳定，尽管在这些条件下会发生氯配体被水或氢氧化物置换的情况。在酸性介质中，Pd–NHC键是被质子分解的，特别值得注意的是，对于具有较少空间受阻的NHC配体的配合物，这种质子分解优先于Pd–烯丙基键的分解。此行为与在二甲基亚砜（dmso）中观察到的行为相反，在二甲基亚砜（dmso）中，用布朗斯台德酸处理后，Pd-烯丙基键选择性地断裂。此外，Pd–NHC键断裂通过加入强的σ供体配体（如氰化物）而得到促进。复杂的1a是在纯净水中在中等条件下（通常为0
• Room-temperature cobalt-catalyzed arylation of aromatic acids: overriding the ortho-selectivity via the oxidative assembly of carboxylate and aryl titanate reagents using oxygen
  作者：Kun-Ming Liu、Rui Zhang、Xin-Fang Duan

  DOI：10.1039/c5ob02496j

  日期：——

  A room temperature phosphine or NHC ligand-free cobalt-catalyzed arylation of (hetero)aromatic acids has been developed.

  室温下，一种无需膦或NHC配体的钴催化的芳香酸（包括杂芳香酸）的芳香基化反应已经开发出来。
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OR PREVENTION OF FLAVIVIRUS INFECTIONS<br/>[FR] COMPOSES ET PROCEDES DE TRAITEMENT OU DE PREVENTION D'INFECTIONS A FLAVIVIRUS
  申请人：VIROCHEM PHARMA INC

  公开号：WO2004052885A1

  公开（公告）日：2004-06-24

  The present invention provides novel compounds represented by formula (I) or pharmaceutically acceptable salts thereof useful for treating flaviviridae viral infection.

  本发明提供了一种表示为式(I)的新化合物，或其在药学上可接受的盐，用于治疗黄病毒科病毒感染。
• Azabicyclic-substituted-heteroaryl compounds for the treatment of disease
  申请人：——

  公开号：US20030207913A1

  公开（公告）日：2003-11-06

  The invention provides compounds of Formula I: Azabicyclo-N(R 1 )—C(═X)—W  Formula I These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful in pharmaceuticals in which &agr;7 is known to be involved.

  这项发明提供了Formula I的化合物： Azabicyclo-N(R1)—C(═X)—W  Formula I 这些化合物可以是药用盐或组合物的形式，或者是它们的消旋混合物，或者是纯对映体。Formula I的化合物在已知涉及α7的药物中是有用的。

表征谱图