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    1. Product Name: 4-ETHYNYLANILINE
    2. Synonyms: 4-ethenylbenzenamine;4-Ethynyl aniline (4-aminophenylacetylene);4-ETHYNYLANILINE 97%;Benzenamine, 4-ethynyl- (9CI);p-Ethnylaniline;4-Ethynylaniline ,98%;4-Ethynylaniline,1-Amino-4-ethynylbenzene;4-Ethynyl-benzenaMine
    3. CAS NO:14235-81-5
    4. Molecular Formula: C8H7N
    5. Molecular Weight: 117.15
    6. EINECS: N/A
    7. Product Categories: Acetylenes;Building Blocks for Liquid Crystals;Chalcones, etc. (Building Blocks for Liquid Crystals);Functional Materials;Functionalized Acetylenes
    8. Mol File: 14235-81-5.mol
    9. Article Data: 82
  • Chemical Properties

    1. Melting Point: 98-102 °C (dec.)(lit.)
    2. Boiling Point: 223.7 °C at 760 mmHg
    3. Flash Point: 98.3 °C
    4. Appearance: Yellow to brown/Crystalline Powder
    5. Density: 1.05 g/cm3
    6. Vapor Pressure: 0.0949mmHg at 25°C
    7. Refractive Index: 1.589
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. PKA: 3.11±0.10(Predicted)
    11. BRN: 2205181
    12. CAS DataBase Reference: 4-ETHYNYLANILINE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 4-ETHYNYLANILINE(14235-81-5)
    14. EPA Substance Registry System: 4-ETHYNYLANILINE(14235-81-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-36/37
    4. WGK Germany: 3
    5. RTECS:
    6. F: 8-10-23
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 14235-81-5(Hazardous Substances Data)

14235-81-5 Usage

Description

4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne with a white or light yellow solid appearance. It is synthesized using 2-methyl-3-butyn-2-ol (MEBYNOL) and has been reported to undergo transition metal catalyzed polymerization to afford poly(4-ethynylaniline). The impact of surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has also been investigated.

Uses

Used in Chemical Synthesis:
4-Ethynylaniline is used as a key component in the synthesis of various organic compounds, such as N-methyliminodiethyl 4-(4-ethynylphenyliminomethyl) benzeneboronate. It plays a crucial role in the formation of these complex molecules, contributing to their unique properties and potential applications.
Used in the Preparation of Acetylene Ligands:
4-Ethynylaniline is utilized in the preparation of acetylene ligands, such as HC2-NDI (NDI = 1,4,5,8-naphthalenediimide). These ligands are essential in various chemical reactions and can be used to modify the properties of metal complexes, enhancing their performance in catalysis and other applications.
Used in the Synthesis of Indoles:
4-Ethynylaniline serves as an alkyne component in the synthesis of indoles from nitroarenes in the presence of a palladium-phenantroline catalyst. Indoles are important organic compounds with a wide range of applications, including pharmaceuticals, agrochemicals, and materials science.
Used in Surface Functionalization:
4-Ethynylaniline is employed in the surface functionalization of multi-walled carbon nanotubes (MWNTs) and graphene, which can significantly impact their thermal behavior. This functionalization can improve the properties of these materials, making them more suitable for various applications, such as energy storage, electronics, and composite materials.

Reaction

4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne. Its synthesis using 2-methyl-3-butyn-2-ol (MEBYNOL) has been reported. The transition metal catalyzed polymerization of 4-ethynylaniline to afford poly(4-ethynylaniline) has been reported.[3]The impact of the surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has been investigated.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 5818, 1994 DOI: 10.1021/jo00098a051

Check Digit Verification of cas no

The CAS Registry Mumber 14235-81-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,3 and 5 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 14235-81:
(7*1)+(6*4)+(5*2)+(4*3)+(3*5)+(2*8)+(1*1)=85
85 % 10 = 5
So 14235-81-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H7N/c1-2-7-3-5-8(9)6-4-7/h1,3-6H,9H2

14235-81-5 Well-known Company Product Price

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  • TCI America

  • (E0505)  4-Ethynylaniline  >98.0%(HPLC)

  • 14235-81-5

  • 10g

  • 1,790.00CNY

  • Detail
  • TCI America

  • (E0505)  4-Ethynylaniline  >98.0%(HPLC)

  • 14235-81-5

  • 25g

  • 2,990.00CNY

  • Detail
  • Aldrich

  • (481122)  4-Ethynylaniline  97%

  • 14235-81-5

  • 481122-5G

  • 1,943.37CNY

  • Detail

14235-81-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Ethynylaniline

1.2 Other means of identification

Product number -
Other names 4-ETHYNYLANILINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14235-81-5 SDS

14235-81-5Relevant articles and documents

Ammonia borane dehydrogenation and selective hydrogenation of functionalized nitroarene over a porous nickel-cobalt bimetallic catalyst

Miao, Hui,Ma, Kelong,Zhu, Huiru,Yin, Kun,Zhang, Ying,Cui, Yumin

, p. 14580 - 14585 (2019)

The hydrolysis of ammonia borane is a promising strategy for hydrogen energy exploration and exploitation. The in situ produced hydrogen could be directly utilized in hydrogenation reactions. In this work, a bimetallic nickel-cobalt material with porous structure was developed through the pyrolysis of ZIF-67 incorporated with Ni ions. Through the introduction of Ni(NO3)2 as an etching agent, the ZIF-67 polyhedrons were transformed into hollow nanospheres, and further evolved into irregular nanosheets. The bimetallic NiCo phase was formed after pyrolysis in a nitrogen atmosphere at high temperature, with the decomposition and release of organic ligands as gaseous molecules under flowing nitrogen. The obtained bimetallic NiCo porous materials show superior catalytic performance towards hydrolytic dehydrogenation of ammonia borane, thereby nitrobenzene with reducible functional groups can be reduced with high selectivity to the corresponding aniline.

Diruthenium phenylacetylide complexes bearing para -/ meta -amino phenyl substituents

Cummings, Steven P.,Cao, Zhi,Liskey, Carl W.,Geanes, Alex R.,Fanwick, Phillip E.,Hassell, Kerry M.,Ren, Tong

, p. 2783 - 2788 (2010)

Presented herein is the synthesis and characterization of four diruthenium(II,III) compounds of formulas Ru2(Xap) 4(C≡C-C6H4-4-NH2) (Xap is 2-anilinopyridinate, 1a; and 2-(3,5-dimethoxy)anilinopyridinate, 1b) and Ru 2(Xap)4(C≡C-C6H4-3-NH 2) (2a/2b). X-ray structural studies of compounds 1b and 2a revealed minimal changes in the coordination sphere of the Ru2 core. Voltammetric measurements showed that compounds 1 exhibit three one-electron redox processes: a reversible reduction of Ru2, a reversible oxidation of Ru2, and a quasi-reversible oxidation of an amino group. Compounds 2 display the same Ru2-based redox processes but not the -NH2 oxidation. Compounds 1a/1b were successfully converted to the corresponding diazonium salts [Ru2(Xap)4-(C≡C-C 6H4-4-N2)](BF4) (3a/3b) via oxidation by nitrosonium tetrafluoroborate, which was generated in situ from t-BuONO and BF3. However, the attempt to convert compounds 2 to the corresponding diazonium salts was unsuccessful. DFT calculations of model compounds were performed to rationalize some unusual structural and electrochemical characteristics observed for compounds 1/2.

Selective hydrogenation of nitroarenes to aminoarenes using a MoO:X-modified Ru/SiO2 catalyst under mild conditions

Tamura, Masazumi,Yuasa, Naoto,Nakagawa, Yoshinao,Tomishige, Keiichi

, p. 3377 - 3380 (2017)

Modification of Ru/SiO2 with metal oxides (MoOx, WOx, and ReOx) improved the activity and selectivity in the hydrogenation of 3-nitrostyrene to 3-aminostyrene under mild conditions such as 0.3 MPa H2, 303 K, and no solvent. Ru-MoOx/SiO2(Mo/Ru = 1/2) catalyst was applicable to various substituted nitroarenes, providing the corresponding substituted aminoarenes in high yields (85-99%).

Using the hydrogen and oxygen in water directly for hydrogenation reactions and glucose oxidation by photocatalysis

Zhou, Baowen,Song, Jinliang,Zhou, Huacong,Wu, Tianbin,Han, Buxing

, p. 463 - 468 (2016)

Direct utilization of the abundant hydrogen and oxygen in water for organic reactions is very attractive and challenging in chemistry. Herein, we report the first work on the utilization of the hydrogen in water for the hydrogenation of various organic compounds to form valuable chemicals and the oxygen for the oxidation of glucose, simultaneously by photocatalysis. It was discovered that various unsaturated compounds could be efficiently hydrogenated with high conversion and selectivity by the hydrogen from water splitting and glucose reforming over Pd/TiO2 under UV irradiation (350 nm). At the same time, glucose was oxidated by the hydroxyl radicals from water splitting and the holes caused by UV irradiation to form biomass-derived chemicals, such as arabinose, erythrose, formic acid, and hydroxyacetic acid. Thus, the hydrogen and oxygen were used ideally. This work presents a new and sustainable strategy for hydrogenation and biomass conversion by using the hydrogen and oxygen in water.

Cobalt nanoparticles encapsulated in nitrogen-doped carbon for room-temperature selective hydrogenation of nitroarenes

Gao, Ruijie,Pan, Lun,Li, Zhengwen,Zhang, Xiangwen,Wang, Li,Zou, Ji-Jun

, p. 664 - 672 (2018)

Here, we report cobalt nanoparticles encapsulated in nitrogen-doped carbon (Co@NC) that exhibit excellent catalytic activity and chemoselectivity for room-temperature hydrogenation of nitroarenes. Co@NC was synthesized by pyrolyzing a mixture of a cobalt

Non-noble metal catalysts for hydrogenation: A facile method for preparing Co nanoparticles covered with thin layered carbon

Liu, Lichen,Concepción, Patricia,Corma, Avelino

, p. 1 - 9 (2016)

Metallic cobalt nanoparticles with surface CoOx patches covered by thin layered carbon (named Co@C) have been directly synthesized by thermal decomposition of Co-EDTA complex. Raman spectra and HRTEM images suggest that discontinuities can be found in the disordered layered carbon. XPS shows that the CoOx patches in the Co@C nanoparticles can reduced to metallic Co by H2 under reaction conditions (7 bar at 120 °C), and H2-D2 exchange experiments show that the reduced metallic Co nanoparticles covered by carbon layers can dissociate H2. The Co@C nanoparticles show excellent activity and selectivity during chemoselective hydrogenation of nitroarenes for a wide scope of substrates under mild reaction conditions. Based on the results from DRIFTS adsorption experiments, we propose that metallic Co in the Co@C nanoparticles is the active phase. The role of the carbon layers is to protect the Co from overoxidation by air, leading to the chemoselective hydrogenation of nitroarenes.

Synthesis and asymmetric catalytic performance of one-handed helical poly(phenylacetylene)s bearing proline dipeptide pendants

Liu, Lijia,Wang, Yaodong,Wang, Fuqingyun,Zhang, Chunhong,Zhou, Yanli,Zhou, Zhengjin,Liu, Xudong,Zhu, Ruiqi,Dong, Hongxing,Satoh, Toshifumi

, (2020)

One-handed helical substituted polyacetylene has received extensive attention due to its potential in chiral stationary phases and molecular recognition. Here, three one-handed helical poly(phenylacetylene)s bearing proline or proline dipeptide as the pen

High Catalytic Activity and Chemoselectivity of Sub-nanometric Pd Clusters on Porous Nanorods of CeO2 for Hydrogenation of Nitroarenes

Zhang, Sai,Chang, Chun-Ran,Huang, Zheng-Qing,Li, Jing,Wu, Zhemin,Ma, Yuanyuan,Zhang, Zhiyun,Wang, Yong,Qu, Yongquan

, p. 2629 - 2637 (2016)

Sub-nanometric Pd clusters on porous nanorods of CeO2 (PN-CeO2) with a high Pd dispersion of 73.6% exhibit the highest catalytic activity and best chemoselectivity for hydrogenation of nitroarenes to date. For hydrogenation of 4-nitr

Molecular design directs self-assembly of DPP polycatenars into 2D and 3D complex nanostructures

Chang, Qing,Cheng, Xiaohong,Du, Xuyang,Ge, Tao,Liu, Xinhao,Ma, Tao

, (2022/02/05)

Novel diketopyrrolopyrrole (DPP) based polycatenars characterized with a long π-conjugated rigid calamitic core, different side groups (t-Boc, H or PEO) at the lactam N atoms of the central DPP core and terminal hydrophobic paraffinic chains were prepared

Sustainable and recyclable palladium nanoparticles–catalyzed reduction of nitroaromatics in water/glycerol at room temperature

Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhao, Yongde,Zhou, Yang

, p. 540 - 544 (2020/07/14)

Palladium nanoparticles with unique catalytic activity and high stability are synthesized. These nanoparticles exhibit excellent catalytic reduction activity for nitroaromatics in green solvents in the presence of H2 at ambient pressure and temperature. The prominent advantages of this nanotechnology include low consumption of catalyst, excellent chemoselectivity, high reusability of the catalyst, and environmentally green solvents.

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