1-Nitro-4-phenylethynyl-benzene

Base Information

• Chemical Name: 1-Nitro-4-phenylethynyl-benzene
• CAS No.: 1942-30-9
• Molecular Formula: C14H9 N O2
• Molecular Weight: 223.231
• Hs Code.: 2904209090
• DSSTox Substance ID: DTXSID40393640
• Nikkaji Number: J361.830G
• Wikidata: Q82192470
• Mol file: 1942-30-9.mol

Synonyms:1942-30-9;1-Nitro-4-phenylethynyl-benzene;1-nitro-4-(2-phenylethynyl)benzene;1-nitro-4-(phenylethynyl)benzene;1-(2-(4-nitrophenyl)ethynyl)benzene;Benzene,1-nitro-4-(2-phenylethynyl)-;UNM-0000306054;Benzene, 1-nitro-4-(phenylethynyl)-;(4-Nitrophenylethynyl)benzene;4-(Phenylethynyl)nitrobenzene;(4-nitrophenyl)phenylacetylene;SCHEMBL7803648;BDBM54696;cid_3560757;AMY7230;DTXSID40393640;MFCD00617151;AKOS005067645;AB91918;1-nitro-4-(2-phenyl-1-ethynyl)benzene;CS-0336634;UNM000011087001

Chemical Property of 1-Nitro-4-phenylethynyl-benzene

Chemical Property:

• PSA: 45.82000
• LogP: 3.51780
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 223.063328530
• Heavy Atom Count: 17
• Complexity: 319

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-NITRO-4-PHENYLETHYNYL-BENZENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 1-Nitro-4-phenylethynyl-benzene

There total 141 articles about 1-Nitro-4-phenylethynyl-benzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-chlorobenzonitrile (100-00-5) + chlorobenzene (108-90-7) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4-(phenylethynyl)nitrobenzene (1942-30-9)

Guidance literature:

With potassium carbonate; palladium dichloride; XPhos; In acetonitrile; at 110 ℃; for 16h; Inert atmosphere; Green chemistry;

DOI:10.1039/c4ra02720e

Reference yield: 99.0%

4-chlorobenzonitrile (100-00-5) + phenylpropyolic acid (637-44-5) → 4-(phenylethynyl)nitrobenzene (1942-30-9)

Guidance literature:

With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; potassium carbonate; XPhos; In 5,5-dimethyl-1,3-cyclohexadiene; water; at 120 ℃; for 3h;

DOI:10.1021/jo400574d

Reference yield: 95.0%

→ 4-(phenylethynyl)nitrobenzene (1942-30-9) + triethylamine hydrobromide (636-70-4)

Guidance literature:

upstream raw materials:

p-nitrostilbene dibromide

α'-chloro-4-nitro-stilbene

(Z)-1-(2-chloro-2-phenylvinyl)-4-nitrobenzene

copper(I) phenylacetylenide

Downstream raw materials:

benzoic acid methyl ester

4-nitrobenzoic acid methyl ester

C₂₉H₂₀N₂O₂

C₂₉H₂₀N₂O₂

Refernces

• 1、 Mas-Marzá, Elena,Segarra, Anna M.,Claver, Carmen,Peris, Eduardo,Fernandez, Elena. "Improved Sonogashira C-C coupling through clay supported palladium complexes with tridentate pincer bis-carbene ligands". . p. 6595 - 6599. Retrieved 2003.
• 2、 Huang, Jinping,Wang, Wei,Li, Hexing. "Water-medium organic reactions catalyzed by active and reusable Pd/Y Heterobimetal-organic framework". . p. 1526 - 1536. Retrieved 2013.
• 3、 Hoseini, S. Jafar,Aramesh, Nahal,Bahrami, Mehrangiz. "Effect of addition of iron on morphology and catalytic activity of PdCu nanoalloy thin film as catalyst in Sonogashira coupling reaction". . . Retrieved 2017.
• 4、 Zhu, Neng-Xiu,Wei, Zhang-Wen,Chen, Cheng-Xia,Wang, Dawei,Cao, Chen-Chen,Qiu, Qian-Feng,Jiang, Ji-Jun,Wang, Hai-Ping,Su, Cheng-Yong. "Self-Generation of Surface Roughness by Low-Surface-Energy Alkyl Chains for Highly Stable Superhydrophobic/Superoleophilic MOFs with Multiple Functionalities". . p. 17033 - 17040. Retrieved 2019.
• 5、 Sabounchei, Seyyed Javad,Ahmadi, Mohsen. "An efficient protocol for copper- and amine-free Sonogashira reactions catalyzed by mononuclear palladacycle complexes containing bidentate phosphine ligands". . p. 114 - 121. Retrieved 2013.
• 6、 Mandegani, Zeinab,Asadi, Mozaffar,Asadi, Zahra. "Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine-free Suzuki reaction in water and copper-free Sonogashira reaction under aerobic conditions". . p. 657 - 663. Retrieved 2016.
• 7、 Sharma, Priti,Singh. "Phosphine free SBA-15-EDTA-Pd highly active recyclable catalyst: Synthesis characterization and application for Suzuki and Sonogashira reaction". . p. 2978 - 2989. Retrieved 2014.
• 8、 Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh. "Pd nanoparticles catalyst supported on TMU-16-NH2 metal-organic framework for Sonogashira cross-coupling reaction". . . Retrieved 2021/12/10.
• 9、 Liu, Qingxiang,Zhang, Xiantao,Zhao, Zhixiang,Li, Xinying,Zhang, Wei. "Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions". supporting information. p. 605 - 613. Retrieved 2021/02/01.