4-(苯乙炔基)苯甲酸 | 25739-23-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 4-(苯乙炔基)苯甲酸
• 中文别名: 4-苯乙炔基苯甲酸
• 英文名称: 4-(phenylethynyl)benzoic acid
• 英文别名: 4-(2-phenylethynyl)benzoic acid
• CAS: 25739-23-5
• 化学式: C₁₅H₁₀O₂
• mdl: MFCD00438677
• 分子量: 222.243
• InChiKey: OGZUGPOTBGMCLE-UHFFFAOYSA-N

物化性质

• 熔点：
  220.5-221.0 °C(Solv: ethanol (64-17-5))
• 沸点：
  407.3±28.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Phenylethynyl-benzoic 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: 4-Phenylethynyl-benzoic acid
CAS number: 25739-23-5

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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, refrigerated.
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: C15H10O2
Molecular weight: 222.2

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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.

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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：

  4-(苯乙炔基)苯甲酸 在 2-氯吡啶-N-氧化物 、 一氯化碘 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以89%的产率得到4-(2-氧代-2-苯基乙酰基)-苯甲酸
  参考文献：
  名称：

  氰化物和二芳基乙炔的无金属碘催化氧化为1,2-二酮化合物

  摘要：

  描述了使用吡啶-N-氧化物作为氧化剂在分子碘催化下的乙酰胺的无金属氧化。与布朗斯台德酸催化形成鲜明对比的是，酰胺的碘键活化将反应歧管转移至双加氧途径。这种氧化在室温下非常迅速，仅需2.5 mol％I 2。此外，该协议可以扩展到未活化的炔烃，例如二芳基乙炔，以递送各种苯甲衍生物。

  DOI：

  10.1021/acs.joc.8b00484
• 作为产物：
  描述：

  4-(苯乙炔基)苯甲醛 在 air 、 N,N’-二羟基-2,3-二甲基-2,3-丁二胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 120.0h， 以55%的产率得到4-(苯乙炔基)苯甲酸
  参考文献：
  名称：

  摘要：

  2-(Arylylethynylphenyl)-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxides 12 and 13 were synthesized by cross-coupling of aryl iodides with 1-alkynes containing the 4,4,5,5-tetramethyl-2-imidazoline- 1-oxyl 3-oxide fragment. A procedure was developed for the preparation of 3- and 4-ethynylbenzaldehydes with the use of 2-methylbut-3-yn-2-ol.

  DOI：

  10.1023/a:1015026200647
• 作为试剂：
  描述：

  ((2R,3R)-3-hydroxy-1-{[4-(trifluoromethoxy)phenyl]carbonyl}pyrrolidin-2-yl)-N-(phenylmethoxy)carboxamide 、 4'-Ethyl-biphenyl-4-carboxylic acid [2-(2-amino-ethylamino)-1-hydroxycarbamoyl-ethyl]-amide 、 四氢呋喃 在 双三苯基磷二氯化钯 、 碘化亚铜 氩 、 四氢呋喃 、 氧气 、 TEA 、 乙酸乙酯 、 盐酸 、 碳酸氢钠 、 水 、 Brine 、 Sodium sulfate-III 、 methyl ester 、 甲醇 、 正己烷 、 4-(苯乙炔基)苯甲酸 作用下， 以 水 、 正己烷 为溶剂， 反应 3.58h， 以was formed (about 1 h)的产率得到4-(苯乙炔基)苯甲酸
  参考文献：
  名称：

  Antibacterial agents

  摘要：

  本发明提供了化学式I的抗菌化合物，包括立体异构体、药学上可接受的盐、酯和前药；包括这些化合物的药物组合物；通过给予这些化合物的途径来治疗细菌感染的方法；以及制备这些化合物的方法。

  公开号：

  US20110172174A1

文献信息

• Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
  作者：Youzhi Wu、Peng Sun、Kaifan Zhang、Tie Yang、Hequan Yao、Aijun Lin

  DOI：10.1021/acs.joc.5b02824

  日期：2016.3.4

  Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an

  本文报道的是初级苯甲酰胺与重氮化合物的Rh催化氧化还原中性环化反应，代表了对异喹啉酮的有效和经济方案。该过程表现出良好的官能团耐受性，可伸缩性，和区域选择性，避免了对氧化剂的需要，并且只对环境无害Ñ 2和H 2 ö被释放。该方法的进一步利用为功能化的异喹啉提供了另一种途径。
• Pd-grafted periodic mesoporous organosilica: an efficient heterogeneous catalyst for Hiyama and Sonogashira couplings, and cyanation reactions
  作者：Arindam Modak、John Mondal、Asim Bhaumik

  DOI：10.1039/c2gc35820d

  日期：——

  alkaline pH conditions. Sonogashira cross-couplings between terminal alkynes and aryl halides take place in the presence of water and hexamine as base in the absence of any Cu co-catalyst. Cyanation of aryl halides is equally promoted with K4[Fe(CN)6] as the cyanide source (in the absence of poisonous KCN, NaCN or Zn(CN)2) over Pd-LHMS-3. Excellent yield of the products, reusability and the facile work-up

  在孔壁内部含有间苯三酚-二亚胺部分的2D-六方周期性介孔有机二氧化硅（PMO）的高表面积已被用于在中孔表面接枝Pd（II）。这种含钯的PMO材料（Pd-LHMS-3）在碱性pH条件下在水中的无氟Hiyama交叉偶联反应中显示出出色的催化活性。末端炔烃与芳基卤化物之间的Sonogashira交叉偶联在水和六胺为碱的情况下，在不存在任何Cu助催化剂的情况下进行。以K 4 [Fe（CN）6 ]作为氰化物源同样地促进芳基卤化物的氰化（在无毒的KCN，NaCN或Zn（CN）2的情况下））在Pd-LHMS-3上。出色的产品收率，可重复使用性和简便的后处理方法可以使这种Pd接枝的PMO材料成为在环境友好的反应条件下合成取代的苄腈，不对称的联苯和二取代的炔烃的独特催化剂。在反应期间产物的进一步良好的产率以及没有Pd从催化剂表面浸出的迹象以及其平滑的回收率证实了这些催化反应中真正的异质性。
• Silver(i)-catalyzed carboxylation of arylboronic esters with CO2
  作者：Xiao Zhang、Wen-Zhen Zhang、Ling-Long Shi、Chun-Xiao Guo、Ling-Ling Zhang、Xiao-Bing Lu

  DOI：10.1039/c2cc32045b

  日期：——

  A variety of arylboronic esters were efficiently carboxylated with CO2 using a simple AgOAc/PPh3 catalyst, affording the corresponding carboxylic acids in good yield. This simple and efficient silver(I) catalytic system showed wide functional group compatibility.

  多种芳基硼酸酯通过简单AgOAc/PPh3催化剂高效地与二氧化碳发生羧基化反应，生成相应的羧酸，产率良好。这一简单高效的银(I)催化体系表现出广泛的官能团兼容性。
• Nickel(II) complexes containing ONS donor ligands: Synthesis, characterization, crystal structure and catalytic application towards C-C cross-coupling reactions
  作者：PANNEERSELVAM ANITHA、RAJENDRAN MANIKANDAN、PARANTHAMAN VIJAYAN、GOVINDAN PRAKASH、PERIASAMY VISWANATHAMURTHI、RAY JAY BUTCHER

  DOI：10.1007/s12039-015-0811-4

  日期：2015.4

  Sonogashira coupling reactions rather than Suzuki-Miyaura coupling. Nickel(II) complexes bearing 9,10-phenanthrenequinone N-substituted thiosemicarbazone ligands were synthesized and characterized. The X-ray crystal structure of the complexes revealed a distorted octahedral geometry around the metal centre. These nickel complexes exhibited better catalytic activity in Kumada-Corriu and Sonogashira

  镍（II）含有缩氨基硫脲配位体[镍（L）配合物2 ]（1 - 3）（L = 9,10- phenanthrenequinonethiosemicarbazone（HL 1），9,10-菲醌-N-甲硫基缩氨基脲（HL 2）和图9，已通过元素分析和光谱法（IR，UV-Vis，1 H，13 C-NMR和ESI质量）合成并表征了10-菲醌-N-苯基硫代半脲（HL 3）。配合物1和2的分子结构通过单晶X射线衍射分析来鉴定。分析表明，该配合物具有扭曲的八面体几何形状，配体以单负三齿ONS方式进行配位。已经研究了复合物对某些C-C偶联反应（即Kumada-Corriu，Suzuki-Miyaura和Sonogashira）的催化活性。该络合物在Kumada-Corriu和Sonogashira偶联反应中，而不是在Suzuki-Miyaura偶联中，起着高效催化剂的作用。 合成并表征了带有9,10-菲醌N
• Hypoglycemic agent
  申请人：Ajinomoto Co., Inc.

  公开号：US20030191323A1

  公开（公告）日：2003-10-09

  The present invention provides a hypoglycemic agent containing an acylsulfonamide derivative such as a compound of the following formula or an analog thereof, which agent is usable for preventing and curing diabetes: 1

  本发明提供一种含有酰磺酰胺衍生物的降糖剂，例如以下式的化合物或其类似物，该剂可用于预防和治疗糖尿病：