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4-bromo-N-[(E)-phenylmethylidene]aniline is an organic compound characterized by its molecular formula C13H10BrN. It features a 4-bromoaniline moiety, which is an aniline (a derivative of benzene with an amino group) substituted with a bromine atom at the 4-position. The compound also has a phenylmethylidene group, which is a phenyl group (a benzene ring) connected to a methylidene group (a carbon double-bonded to two other atoms). The phenylmethylidene is in the E configuration, indicating the geometric arrangement of the double bond. 4-bromo-N-[(E)-phenylmethylidene]aniline is often used in the synthesis of various pharmaceuticals and dyes due to its unique structural properties.

1750-23-8

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1750-23-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1750-23-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,5 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1750-23:
(6*1)+(5*7)+(4*5)+(3*0)+(2*2)+(1*3)=68
68 % 10 = 8
So 1750-23-8 is a valid CAS Registry Number.

1750-23-8Relevant academic research and scientific papers

Multistep Wavelength Switching of Near-Infrared Photoluminescence Driven by Chemical Reactions at Local Doped Sites of Single-Walled Carbon Nanotubes

Shiraki, Tomohiro,Shiga, Tamehito,Shiraishi, Tomonari,Onitsuka, Hisashi,Nakashima, Naotoshi,Fujigaya, Tsuyohiko

, p. 19162 - 19165 (2018)

Local chemical functionalization is used for defect doping of single-walled carbon nanotubes (SWNTs), to develop near-infrared photoluminescence (NIR PL) properties. We report the multistep wavelength shifting of the NIR PL of SWNTs through chemical react

Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light

Kawamoto, Takuji,Morioka, Tsubasa,Noguchi, Kohki,Curran, Dennis P.,Kamimura, Akio

supporting information, p. 1825 - 1828 (2021/03/08)

We describe a simple and efficient procedure for nucleophilic borylation of imines in the absence of a photoredox catalyst. Visible light irradiation of an acetonitrile solution of an imine, an NHC-borane, and diphenyl disulfide (10 mol %) provides various stable α-amino NHC-boranes in good yields. The reaction proceeds via addition of a nucleophilic boryl radical to an imine, followed by hydrogen abstraction from thiophenol, which is generated from NHC-borane and diphenyl disulfide.

A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water

Ghamari Kargar, Pouya,Ravanjamjah, Asiye,Bagherzade, Ghodsieh

, p. 1916 - 1933 (2021/07/10)

In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.

Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines

Wu, Di,Bu, Qingqing,Guo, Cheng,Dai, Bin,Liu, Ning

, (2021/02/02)

Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.

A Highly Selective Manganese-Catalyzed Synthesis of Imines under Phosphine-Free Conditions

Chai, Huining,Yu, Kun,Liu, Bo,Tan, Weiqiang,Zhang, Guangyao

, p. 217 - 226 (2020/01/31)

An efficient and highly selective phosphine-free NN-manganese(I) complex catalyst system was developed for the acceptorless dehydrogenative coupling of alcohols with amines to form imines. The coupling reactions underwent at 3 mol % catalyst loading, and a large range of alcohols and amines with diverse functional groups was applied, including challenging diol and diamine. The target imine products were obtained in good to excellent yields. The present work provides an alternative method to construct highly active nonprecious metal complex catalysts based on phosphine-free ligands.

Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines

Zhou, Nengneng,Yuan, Xiang-Ai,Zhao, Yue,Xie, Jin,Zhu, Chengjian

supporting information, p. 3990 - 3994 (2018/03/21)

The first catalytic inverse hydroboration of imines with N-heterocyclic carbene (NHC) boranes has been realized by means of cooperative organocatalysis and photocatalysis. This catalytic combination provides a promising platform for promoting NHC-boryl radical chemistry under sustainable and radical-initiator-free conditions. The highly important functional-group compatibility and possible application in late-stage hydroborations represent an important step forward to an enhanced α-amino organoboron library.

Rhodium-catalyzed synthesis of imines and esters from benzyl alcohols and nitroarenes: Change in catalyst reactivity depending on the presence or absence of the phosphine ligand

Song, Taemoon,Park, Ji Eun,Chung, Young Keun

, p. 4197 - 4203 (2018/04/14)

The [Rh(COD)Cl]2/xantphos/Cs2CO3 system efficiently catalyzes the reductive N-alkylation of aryl nitro compounds with alcohols by a borrowing-hydrogen strategy to afford the corresponding imine products in good to excellent yields. In the absence of xantphos, the [Rh(COD)Cl]2/Cs2CO3 catalytic system behaves as an effective catalyst for the dehydrogenative coupling of alcohols to esters, with nitrobenzene as a hydrogen acceptor. The reactivity of the rhodium catalytic system can be easily manipulated to selectively afford the imine or ester.

Enantioselective and Regiodivergent Functionalization of N-Allylcarbamates by Mechanistically Divergent Multicatalysis

Richmond, Edward,Khan, Ismat Ullah,Moran, Joseph

supporting information, p. 12274 - 12277 (2016/08/24)

A pair of mechanistically divergent multicatalytic reaction sequences has been developed consisting of nickel-catalyzed isomerization of N-allylcarbamates and subsequent phosphoric-acid-catalyzed enantioselective functionalization of the resulting intermediates. By appropriate selection of reaction partners, in situ generated imines and ene-carbamates are mechanistically partitioned to yield opposing functionalized products. Formal α-functionalization to give protected α-arylamines is achieved upon enantioselective Friedel–Crafts reaction with arene nucleophiles, whereas formal β-functionalization is achieved upon reaction with diarylimine electrophiles in an enantioselective Povarov-[4+2] cycloaddition.

Solvent-free synthesis of azomethines, spectral correlations and antimicrobial activities of some E-benzylidene-4-chlorobenzenamines

Suresh,Sakthinathan,Kamalakkannan,Ranganathan,Sathiyamoorthi,Mala,Arulkumaran,Vijayakumar,Sundararajan,Vanangamudi,Subramanian,Thirunarayanan,Vanaja,Kanagambal

, p. 275 - 290 (2015/07/27)

Some azomethines including substituted benzylidene-4-chlorobenzenamines (E-imines) have been synthesized by fly-ash: PTS catalyzed microwave assisted condensation of 4-chloroaniline and substituted benzaldehydes under solvent-free conditions. The yield of the imines has been found to be more than 85%. The purity of all imines has been checked using their physical constants and UV, IR and NMR spectral data. These spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of all imines have been studied using standard methods.

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Aspinall, Helen C.,Greeves, Nicholas,Hin, Shane Lo Fan

experimental part, p. 1558 - 1561 (2010/06/13)

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

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