4-Ethynylaniline

Base Information

• Chemical Name: 4-Ethynylaniline
• CAS No.: 14235-81-5
• Molecular Formula: C8H7N
• Molecular Weight: 117.15
• Hs Code.: 29214990
• European Community (EC) Number: 628-948-6
• DSSTox Substance ID: DTXSID90396040
• Nikkaji Number: J607.821D
• Wikidata: Q72477687
• Mol file: 14235-81-5.mol

Synonyms:4-Ethynylaniline;14235-81-5;4-Aminophenylacetylene;Benzenamine, 4-ethynyl-;4-ethynyl aniline;p-ethynylaniline;p-aminophenylacetylene;MFCD00168824;1-Amino-4-ethynylbenzene;4-ethynylaniline-;4-Ethynyl-benzenamine;4-Ethynyl-phenylamine;p-aminophenyl-acetylene;(4-ethynylphenyl)amine;4-Ethynylaniline, 97%;(4-ethynyl-phenyl)-amine;SCHEMBL106193;4-H2N-C6H4-CCH;AMY1231;DTXSID90396040;CHEBI:167803;BBL101148;STL554944;AKOS005257063;CS-W004660;PB40609;SY035744;E0505;FT-0618433;EN300-85313;F13709;1T-1123;J-007642;J-515309

Chemical Property of 4-Ethynylaniline

Chemical Property:

• Vapor Pressure: 0.0949mmHg at 25°C
• Melting Point: 98-102 °C (dec.)(lit.)
• Refractive Index: 1.589
• Boiling Point: 223.7 °C at 760 mmHg
• PKA: 3.11±0.10(Predicted)
• Flash Point: 98.3 °C
• Density: 1.05 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 123

Purity/Quality:

98%, ^*data from raw suppliers

4-Ethynylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC=C(C=C1)N
• Description: 4-Ethynylaniline (also known as p-Alkynylaniline) has amino and ethynyl substitutions in the para position of the benzene ring. It is likely a solid at room temperature and may exhibit solubility in appropriate solvents. 4-Ethynylaniline consists of a benzene ring with an amino group (-NH2) and an ethynyl group (-C≡CH) attached in the para position.
• Uses and Mechanism of Action: In electrochemical oxidation: ; 4-Ethynylaniline can undergo electrochemical oxidation to form various products, including diazine compounds and quinone-imines, depending on reaction conditions and pH.^[1]; ; In surface plasmon-driven reactions: ; 4-Ethynylaniline participates in surface plasmon photocatalytic reactions on metal surfaces, leading to selective coupling reactions and the formation of new compounds such as p,p′-diynylazobenzene.^[2]; ; In organic synthesis: ; 4-Ethynylaniline serves as a nucleophile in electrochemical synthesis reactions, leading to the formation of new quinone-imine derivatives when reacted with substituted catechols.^[3]
• Production Methods: 4-Ethynylaniline is synthesized in the laboratory through chemical reactions involving ethynyl and amino precursors.
• Analysis Method: The behavior of 4-Ethynylaniline and its reaction products can be analyzed using various electrochemical techniques such as cyclic voltammetry and controlled potential coulometry. Surface-enhanced Raman spectroscopy (SERS) is also employed to study plasmon-driven reactions on metal surfaces.
• References: [1] Electrochemical oxidation of 4-ethynylaniline: A green electrochemical protocol for the synthesis of diazine compounds; DOI 10.1016/j.electacta.2021.138242; [2] Plasmon-driven surface catalytic reaction of 4-ethynylaniline in a liquid environment; DOI 10.1039/C8RA03326A; [3] Electrochemical synthesis of new quinone-imines with assisted of 4-ethynylaniline and para-toluidine as nucleophile; DOI 10.1016/j.electacta.2022.140849

Technology Process of 4-Ethynylaniline

There total 25 articles about 4-Ethynylaniline 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-trimethylsilylethynyl aniline (75867-39-9) → 4-Ethynylaniline (14235-81-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/om500265s

Reference yield: 98.0%

(4-Nitrophenyl)acetylene (937-31-5) → 4-Ethynylaniline (14235-81-5)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 4h; chemoselective reaction;

DOI:10.1021/acscatal.5b00830

Reference yield: 98.0%

4-(4-aminophenyl)-2-methyl-3-butyn-2-ol trifluoroacetamide (158074-65-8) → 4-Ethynylaniline (14235-81-5)

Guidance literature:

With potassium hydroxide; In isopropyl alcohol; for 2.5h; Heating;

DOI:10.1021/jo00098a051

upstream raw materials:

(4-Nitrophenyl)acetylene

4-trimethylsilylethynyl aniline

<4-(4-aminophenyl)>-2-methyl-3-butyn-2-ol

4-(4-aminophenyl)-2-methyl-3-butyn-2-ol trifluoroacetamide

Downstream raw materials:

p-(5-methyl-5-hydroxy-1,3-hexadiynyl)aniline

4-(2-(4-aminophenyl)ethynyl)benzonitrile

methyl 4-((4-aminophenyl)ethynyl)benzoate

1-(4-Ethynyl-phenyl)-6,6-dimethyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine; hydrochloride

Refernces

• 1、 Li, Dan-dan,Zhang, Jia-wei,Cai, Chun. "Chemoselective hydrogenation of nitroarenes catalyzed by cellulose-supported Pd NPs". . p. 47 - 50. Retrieved 2018.
• 2、 Ang, Wee Han,Ong, Jun Xiang. "Development of a Pre-assembled Through-Bond Energy Transfer (TBET) Fluorescent Probe for Ratiometric Sensing of Anticancer Platinum(ll) Complexes". . . Retrieved 2020.
• 3、 Luo, Jiao,Liu, Meiling,Zhao, Qiangqin,Zhao, Jie,Zhang, Youyu,Tan, Liang,Tang, Hao,Xie, Qingji,Li, Haitao,Yao, Shouzhuo. "A study on the electro-oxidation and electropolymerization of a new OPE linear molecule by EQCM and in situ FTIR spectroelectrochemistry". . p. 454 - 462. Retrieved 2010.
• 4、 Gao, Ruijie,Pan, Lun,Lu, Jinhui,Xu, Jisheng,Zhang, Xiangwen,Wang, Li,Zou, Ji-Jun. "Phosphorus-Doped and Lattice-Defective Carbon as Metal-like Catalyst for the Selective Hydrogenation of Nitroarenes". . p. 4287 - 4294. Retrieved 2017.
• 5、 Vasilevsky, Sergei F.,Klyatskaya, Svetlana V.,Elguero, José. "One-pot synthesis of monosubstituted aryl(hetaryl)acetylenes by direct introduction of the C≡CH residue into arenes and hetarenes". . p. 6685 - 6688. Retrieved 2004.
• 6、 Morse, James R.,Callejas, Juan F.,Darling, Albert J.,Schaak, Raymond E.. "Bulk iron pyrite as a catalyst for the selective hydrogenation of nitroarenes". . p. 4807 - 4810. Retrieved 2017.
• 7、 Ren, Yuqi,Hao, Caihong,Chang, Qing,Li, Ning,Yang, Jinlong,Hu, Shengliang. "Boosting chemoselective reduction of 4-nitrostyreneviaphotoinduced energetic electrons fromin situformed Cu nanoparticles on carbon dots". . p. 2938 - 2943. Retrieved 2021.
• 8、 Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao. "Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes". . . Retrieved 2022/01/11.
• 9、 -. "Preparation method of acetenyl aniline". Paragraph 0079; 0082. . Retrieved 2021/04/14.