4-Methoxyphenylacetylene - ≥99% , CAS No.768-60-5

CAS: 768-60-5 Cat. No.: M111332 Peso molecular: 132.16 Beilstein Registry Number: 6(4)4064 Número EC: 640-179-8

GRADE & PURITY ≥99%

Synonyms

SY013463 | 4-methoxyphenylethyne | EN300-83248 | p-Methoxyphenylethyne | Z1080385508 | p-ethynylanisole | 1-Ethynyl-4-methoxybenzene # | 4-ethynyl anisole | 4'-Methoxyphenylacetylene | 4-Methoxyphenylacetylene | 4-methoxy-phenylacetylene | 4-Ethynylanisol

Storage

Argon charged,Room temperature

Shipped In

Normal

Descripción general

4-Ethynylanisole forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt. 1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.
4-Ethynylanisole can be used as a building block in organic synthesis and also used in sonogashira coupling reactions. 
Application
1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.
4-Ethynylanisole was used:
in the synthesis of photoluminescent 1,2-dihydrophosphinines via a [4 + 2] cycloaddition
along with an arylboronic acid and sodium azide in a copper-catalyzed, three-component synthesis of trisubstituted 1,2,4-triazoles
in a study of a gold (III)-catalyzed hydroamination of alkynes leading to N-vinylindoles.
Forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt.

Specifications

Sinónimos

SY013463 | 4-methoxyphenylethyne | EN300-83248 | p-Methoxyphenylethyne | Z1080385508 | p-ethynylanisole | 1-Ethynyl-4-methoxybenzene # | 4-ethynyl anisole | 4'-Methoxyphenylacetylene | 4-Methoxyphenylacetylene | 4-methoxy-phenylacetylene | 4-Ethynylanisol

Especificaciones y pureza

≥99%

Condiciones de almacenamiento de almacenamiento

Argon charged, Room temperature

Enviado en

Normal

Pureza

≥99%

Nombres e identificadores

• Pubchem Sid: 504758109
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758109
• Sonrisas canónicas: COC1=CC=C(C=C1)C#C
• IUPAC Name: 1-ethynyl-4-methoxybenzene
• InChIKey: KBIAVTUACPKPFJ-UHFFFAOYSA-N
• INCHI: 1S/C9H8O/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3
• Isómeros SMILES: COC1=CC=C(C=C1)C#C
• WGK Alemania: 3
• Peso molecular: 132.16
• Beilstein: 6(4)4064
• Reaxy-Rn: 742173
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=742173&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Phenol ethers
      • Subclass Anisoles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Phenol ethers
• Subclass: Anisoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Anisoles
• Alternative Parents: Phenoxy compounds Methoxybenzenes Alkyl aryl ethers Acetylides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Methoxybenzene - Anisole - Alkyl aryl ether - Monocyclic benzene moiety - Acetylide - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Insoluble in water. Soluble in chloroform, acetone, dichloromethane, and methanol
• Sensibilidad: Light sensitive;air sensitive;heat sensitive
• Índice de refracción: 1.564
• Punto de inflamación (°F): 179.6 °F
• Punto de inflamación (°C): 82 °C
• Punto de ebullición (°C): 87-91 °C/11 mmHg
• Punto de fusión (°C): 28-29°C
• Peso molecular: 132.160 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 132.058 Da
• Monoisotopic Mass: 132.058 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 134.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Qingxia Zhu, Xiaowen Lu, Siqi Ji, Honghong Li, Jun Wang, Zhijun Li.  (2021)  Fully exposed cobalt nanoclusters anchored on nitrogen-doped carbon synthesized by a host-guest strategy for semi-hydrogenation of phenylacetylene.  JOURNAL OF CATALYSIS,      [PMID:] [10.1016/j.jcat.2021.11.021]

2. Minkang Li, Lina Zhang, Zhongzheng Zhang, Jialin Shi, Yuefeng Liu, Jiansong Chen, Nannan Sun, Wei Wei.  (2021)  SiO2-Coated Ag Nanoparticles for Conversion of Terminal Alkynes to Propolic Acids via CO2 Insertion.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.1c01101]

3. Pan Jiang, Hongkun Li, Wei Liu, Yi Li, Baozong Li, Yonggang Yang.  (2021)  Silica covering driven intensity enhancement and handedness inversion of the CPL signals of the supramolecular assemblies.  NEW JOURNAL OF CHEMISTRY,  45  (20): (8986-8992).  [PMID:] [10.1039/D1NJ01327K]

4. Zhijun Li, Qinghui Ren, Xuexia Wang, Wenxing Chen, Leipeng Leng, Mingyang Zhang, J. Hugh Horton, Bo Liu, Qian Xu, Wei Wu, Jun Wang.  (2021)  Highly Active and Stable Palladium Single-Atom Catalyst Achieved by a Thermal Atomization Strategy on an SBA-15 Molecular Sieve for Semi-Hydrogenation Reactions.  ACS Applied Materials & Interfaces,      [PMID:33412851] [10.1021/acsami.0c17570]

5. Cheng Yuan, Qiqi Wu, Ke-Xin Xu, Xing-Shi Liu, Hao Lou, Yi-Tong Xu, Zheng Li, Yuanyuan Meng, Tan Li, Rui Ban, Guangxu Chen, Wei-Wei Zhao.  (2024)  Metal-organic polymer enables efficient organic photoelectrochemical transistor biosensing.  BIOSENSORS & BIOELECTRONICS,      [PMID:38688230] [10.1016/j.bios.2024.116346]

6. Qian Zhengyi, Han Guokang, Tan Yingjun, Ye Na, Wang Shuguang, Lin Zheng, Huang Qizheng, Gu Yu, Guo Hongyu, Liu Fei, Wang Kai, Li Lu, Shang Changshuai, Luo Mingchuan, Guo Shaojun.  (2025)  σ-π dative bond stabilizing copper active site drives CO2 electrocatalysis to hydrocarbon.  Nature Communications,      [PMID:41381480] [10.1038/s41467-025-66140-w]