56512-48-2

Upstream product

• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 4033-14-1 1,1-bis-(1,1-dimethyl-prop-2-ynyloxy)-ethane 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 17573-94-3 4-ethynyl-N,N-dimethylaniline 
• 58300-70-2 bis(p-dimethylaminophenyl)butadiyne 
• 778593-53-6 1-(p-N,N-dimethylaminophenyl)-2-(p-ethynylphenyl)ethyne 
• 885325-36-0 1-[p-(3-hydroxy-3-methyl-1-butynyl)phenyl]-2-(p-N,N-dimethylaminophenyl)ethyne 
• 778593-54-7 2,5-bis(para-N,N-dimethylaminophenylethynyl)thiophene 
• 62063-67-6 bis(4-dimethylaminophenyl)ethyne 

Relevant academic research and scientific papers

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

Efficient Microwave-Assisted Synthesis of Sonogashira-Coupled Perylene Monoimide Derivatives: Impact of Electron-Donating Groups on Optoelectronic Properties

An efficient microwave-assisted Sonogashira-coupling protocol for the synthesis of peri-functionalized perylene monoimide dye derivatives was developed. This method was found to be significantly faster than the conventional coupling method and provided pr

Synthesis and Simple Immobilization of Palladium(II) Acyclic Diaminocarbene Complexes on Polystyrene Support as Efficient Catalysts for Sonogashira and Suzuki-Miyaura Cross-Coupling

Immobilization of palladium(II) acyclic diaminocarbene (Pd(II)-ADC) complexes on a resin support surface has been easily performed by metal-mediated addition of amino groups of benzhydrylamine-polystyrene to the coordinated isocyanide ligand of cis-PdCl2(CNR)2 (R = t-Bu, Cy). The investigation of the benzhydrylamine reaction with palladium-coordinated isocyanides in solution has revealed that, depending on the reaction conditions, two carbene-type complexes can be obtained as a result of the addition to the CN triple bond, as well as a third complex which is formed via substitution of the isocyanide ligand by benzhydrylamine. Nucleophilic addition of an amino group to the isocyanide ligand has led to a cis-acyclic diaminocarbene complex or a cationic diaminocarbene complex with trans configuration and an intramolecular hydrogen-bonded chloride anion (the nature of this noncovalent interaction was analyzed by DFT calculations, including AIM analysis). The unsupported and resin-supported palladium catalysts have demonstrated high catalytic activity in both Sonogashira and Suzuki-Miyaura cross-coupling. The supported catalyst can be recovered and repeatedly reused without a significant loss in efficiency. The degree of the palladium binding with polystyrene, the oxidation state, and the palladium leaching level were investigated by XPS and XRF analyses.

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.

Elongation of the molecular probe DDNP with phenylethynylidene or phenyldiazenylidene spacers

In this work, we report the synthesis, X-ray structures, and optical properties of two DDNP analogs containing an unsaturated spacer inserted between the donor N,N-dimethylamino group and the naphthalene ring. The new compounds have longer distances betwe

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

Synthesis and properties of novel liquid crystalline materials with super high birefringence: styrene monomers bearing diacetylenes, naphthyl, and nitrogen-containing groups

Three new liquid crystal asymmetrical styrene monomers bearing diacetylenes, naphthyl, and nitrogen-containing groups were successfully synthesized from 2-(bromoethynyl)-6-(hexyloxy)naphthalene, 4-(4-bromo-2-vinylphenyl)-2-methylbut-3-yn-2-ol, and derivat

PROCESS FOR PRODUCING PHOSPHONIUM BORATE COMPOUND, NOVEL PHOSPHONIUM BORATE COMPOUND, AND METHOD OF USING THE SAME

The invention relates to a phosphonium borate compound represented by Formula (I) (hereinafter, the compound (I)). The invention has objects of providing (A) a novel process whereby the compound is produced safely on an industrial scale, by simple reaction operations and in a high yield; (B) a novel compound that is easily handled; and (C) novel use as catalyst. ????????Formula (I) : (R1)(R2)(R3)PH·BAr4?????(I) wherein R1, R2, R3 and Ar are as defined in the specification. The process (A) includes reacting a phosphine with a) HCl or b) H2SO4 to produce a) a hydrochloride or b) a sulfate; and reacting the salt with a tetraarylborate compound. The compound (B) has for example a secondary or tertiary alkyl group as R1 and is easily handled in air without special attention. The use (C) is characterized in that the compound (I) is used instead of an unstable phosphine compound of a transition metal complex catalyst for catalyzing C-C bond, C-N bond and C-O bond forming reactions and the compound produces an effect that is equal to that achieved by the transition metal complex catalyst.

Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: Fluorescence properties

Nano conjugated thienylethenyl and thienylethynyl compounds with controlled structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynyl)phenylacetylene (or thienylethenyl) phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2- thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1- ethynyl]-2,5-di(phenylethynyl)nthiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield.

Synthesis and non-linear optical properties of new ionic species: Tolan and diphenylbutadiyne with trimethylammonio and dimethylamino groups

As new ionic organic species for second-order non-linear optical (NLO) materials, 4-{[4-(dimethylamino)phenyl]ethynyl)phenyltrimethylarnmonium iodide (1a), 4-{[4-(dimethylamino)phenyl]butadiynyl}phenyltri-methylammoniura iodide (2a) and their derivatives