17573-94-3

Basic information

• Product Name: 4'-DIMETHYLAMINOPHENYL ACETYLENE
• Synonyms: 1-ETHYNYL-4-DIMETHYLANILINE;4'-DIMETHYLAMINOPHENYL ACETYLENE;4-DIMETHYLAMINOPHENYLACETYLENE;4-ETHYNYL-N,N-DIMETHYLBENZENAMINE;(4-ETHYNYL-PHENYL)-DIMETHYL-AMINE;N,N-DIMETHYL-4-ETHYNYLBENEZEAMINE;Benzenamine, 4-ethynyl-N,N-dimethyl- (9CI);4-ethynyl-n,n-dimethylaniline
• CAS NO: 17573-94-3
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.2
• Mol File: 17573-94-3.mol
• Article Data: 65

Chemical Properties

• Melting Point: 49-53 °C(lit.)
• Boiling Point: 227.938 °C at 760 mmHg
• Flash Point: 83.404 °C
• Appearance: /
• Density: 0.989 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.30±0.12(Predicted)
• CAS DataBase Reference: 4'-DIMETHYLAMINOPHENYL ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-DIMETHYLAMINOPHENYL ACETYLENE(17573-94-3)
• EPA Substance Registry System: 4'-DIMETHYLAMINOPHENYL ACETYLENE(17573-94-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 17573-94-3(Hazardous Substances Data)

Usage

Description

4'-DIMETHYLAMINOPHENYL ACETYLENE, also known as 4-Ethynyl-N,N-dimethylaniline, is an organic compound with a unique structure that features an ethynyl group attached to a dimethylaniline moiety. It can be synthesized through the hydrolysis of 4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline using potassium hydroxide in toluene. 4'-DIMETHYLAMINOPHENYL ACETYLENE serves as a versatile building block in the synthesis of various advanced materials and molecules.

Uses

Used in Chemical Synthesis:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a synthetic intermediate for the creation of various complex organic molecules and materials. Its unique structure allows for further functionalization and incorporation into a wide range of applications.
Used in Copper(I) Arylacetylide Synthesis:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a starting material for the synthesis of copper(I) arylacetylide via a reaction with copper(II) acetate. This application is significant in the development of new copper-based compounds with potential applications in various fields, such as catalysis and materials science.
Used in Sonogashira–Hagihara Coupling:
In the field of organic chemistry, 4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a reactant in the Sonogashira–Hagihara coupling with 3-iodopyridine. This coupling reaction is a powerful method for the formation of carbon-carbon bonds, leading to the synthesis of N,N-dimethyl-4-(3-pyridinylethynyl)aniline, which can be further utilized in the development of novel organic compounds and materials.
Used in Porphyrin Chemistry:
4'-DIMETHYLAMINOPHENYL ACETYLENE is used as a key component in the synthesis of complex porphyrin derivatives, such as [5,15-bis[(40-dimethylamino)phenyl]ethynyl]-10,20-bis[(triisopropylsilyl)ethynyl]porphyrinato]magnesium(II), through a reaction with dibromo magnesium porphyrin. Porphyrin-based compounds have a wide range of applications, including in the fields of photovoltaics, catalysis, and biomedicine.

Upstream product

• 61503-06-8 3-[4-(dimethylamino)phenyl]-3-chloroprop-2-enal 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 77215-30-6 [4-(1-Bromo-vinyl)-phenyl]-[1-(4-dimethylamino-phenyl)-vinyl]-dimethyl-ammonium 
• 55894-19-4 p-dimethylamino-α-bromostyrene 
• 156780-40-4 (Z)-β-bromo-4-(N,N-dimethylamino)styrene 
• 519-73-3 triphenylmethane 
• 136482-75-2 C₁₀H₁₀KN 
• 40230-97-5 N,N-dimethyl-4-[(trimethylsilyl)ethynyl]aniline 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 124-38-9 carbon dioxide 
• 14235-81-5 4-Ethynylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 119754-15-3 4-ethynyl-N-methylbenzenamine 

Downstream Products

• 58300-70-2 bis(p-dimethylaminophenyl)butadiyne 
• 242487-89-4 1-phenyl-5-(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-ol 
• 242487-86-1 1,5-bis(4-N,N-dimethylaminophenyl)-1,4-pentadiyn-3-ol 
• 62167-09-3 4-((4-methoxyphenyl)ethynyl)-N,N-dimethylbenzenamine 
• 571187-32-1 B(C₆(CH₃)4I)(C₆(CH₃)4CCC₆H₄N(CH₃)2)2 
• 596135-37-4 8-tert-butoxycarbonyloxy-5-(4-dimethylaminophenylethynyl)quinoline 
• 568592-14-3 {4-[7-bromo-9-(4-trimethylsilanylethynylphenyl)-9H-carbazol-2-ylethynyl]phenyl}dimethylamine 
• 568592-21-2 dimethyl-{4-[6-(4-nitrophenylethynyl)-9-(4-trimethylsilanylethynylphenyl)-9H-carbazol-3-ylethynyl]phenyl}amine 
• 885325-36-0 1-[p-(3-hydroxy-3-methyl-1-butynyl)phenyl]-2-(p-N,N-dimethylaminophenyl)ethyne 
• 937701-53-6 C₂₂H₂₇NO₄ 
• 937701-52-5 C₂₀H₂₃NO₃ 
• 885515-77-5 4-[4-(trimethylsilyl)buta-1,3-diyn-1-yl]-N,N-dimethylaniline 
• 885515-78-6 N,N-dimethyl-4-[(triisopropylsilyl)buta-1,3-diyn-1-yl]aniline 
• 945716-86-9 [4-(6-chloro-2-methyl-5-phenylpyrimidin-4-ylethynyl)phenyl]dimethylamine 

Relevant articles and documents

Benzobisimidazole Cruciform Fluorophores

A series of 11 cross-conjugated cruciform fluorophores based on a benzobisimidazole nucleus has been synthesized and characterized. Like in their previously reported benzobisoxazole counterparts, the HOMOs of these new fluorophores are localized along the vertical bisethynylbenzene axes, while their LUMOs remain relatively delocalized across the molecule, except in cruciforms substituted with electron-withdrawing groups along the vertical axis. Benzobisimidazole cruciforms exhibit a pronounced response to deprotonation in their UV/vis absorption and emission spectra, but their response to protonation is significantly attenuated. (Chemical Equation Presented).

A Porous and Solution-Processable Molecular Crystal Stable at 200 °c: The Surprising Donor-Acceptor Impact

We report a curious porous molecular crystal that is devoid of the common traits of related systems. Namely, the molecule does not rely on directional hydrogen bonds to enforce open packing, and it offers neither large concave faces (i.e., high internal f

Synthesis, Crystal Structures, and Solid-State Polymerization of 8?[4-(Dimethylamino)phenyl]octa-5,7-diynyl Carbamates

Six butadiyne monomers with (dimethylamino)phenyl and N-substituted urethane substituents were synthesized and their crystal structures and solid-state polymerization were investigated. In five of the six monomers, directions of the butadiyne stacking and

Synthesis and Solid-State Polymerization of 4-(Dimethylamino) phenylbutadiyne Derivatives and Their Charge-Transfer Complexes

(Five urethane derivatives of 8-[4-(dimethylamino)phenyl]octa-5,7-diyn-1-ol were synthesized. They could be polymerized in the solid state to give conjugated backbones although structural regularity seemed to be not so high. Formability of chargetransfer

Combinatorial synthesis of new fluorescent scaffolds using click chemistry

Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.

Near-Infrared Fluorescent Probes with Rotatable Polyacetylene Chains for the Detection of Amyloid-β Plaques

The plaques of accumulated β-amyloid (Aβ) in the parenchymal brain are accepted as an important biomarker for the early diagnosis of Alzheimer's disease (AD). Many near-infrared (NIR) probes, which were based on the D-π-A structure and bridged by conjugat

Donor-acceptor substituted benzo-, naphtho- and phenanthro-fused norbornadienes

The photochromic norbornadiene/quadricyclane (NBD/QC) couple has found interest as a molecular solar thermal energy (MOST) system for storage of solar energy. To increase the energy difference between the two isomers, we present here the synthesis of a selection of benzo-fused NBD derivatives that contain an aromatic unit, benzene, naphthalene or phenanthrene, fused to one of the NBD double bonds, while the carbon atoms of the other double bond are functionalized with donor and acceptor groups. The synthesis protocols involve functionalization of benzo-fused NBDs with bromo/chloro substituents followed by a subjection of these intermediates to a cyanation reaction (introducing a cyano acceptor group) followed by a Sonogashira coupling (introducing an arylethynyl donor group, -C≡CC6H4NMe2 or -C≡CC6H4OMe). While the derivatives have good absorption properties in the visible region (redshifted relative to parent system) in the context of MOST applications, they lack the ability to undergo NBD-to-QC photoisomerization, even in the presence of a photosensitizer. It seems that loss of aromaticity of the fused aromatics is too significant to allow photoisomerization to occur. The concept of destroying aromaticity of a neighboring moiety as a way to enhance the energy density of the NBD/QC couple thus needs further structural modifications, in the quest for optimum MOST systems.