102904-39-2

Basic information

• Product Name: (E)-1-phenyl-N-(4-iodophenyl)methanimine
• Synonyms: (E)-1-phenyl-N-(4-iodophenyl)methanimine
• CAS NO: 102904-39-2
• Molecular Weight: 307.134
• Mol File: 102904-39-2.mol

Chemical Properties

• CAS DataBase Reference: (E)-1-phenyl-N-(4-iodophenyl)methanimine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-phenyl-N-(4-iodophenyl)methanimine(102904-39-2)
• EPA Substance Registry System: (E)-1-phenyl-N-(4-iodophenyl)methanimine(102904-39-2)

Safety Data

• Hazardous Substances Data: 102904-39-2(Hazardous Substances Data)

Upstream product

• 540-37-4 p-aminoiodobenzene 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 5636-99-7 N,N'-bis(4-iodophenyl)formamidine 
• 16430-09-4 3-methyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 636-98-6 p-nitrobenzene iodide 
• 538-51-2 benzylidene phenylamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-46-9 benzylamine 

Downstream Products

• 94871-48-4 [3-(phenyl)-3-((4-iodophenyl)amino)-1-phenylpropan-1-one] 
• 2948-41-6 N,N'-Bis-(4-jodphenyl)-1,2-diphenyl-aethylendiamin 
• 116027-51-1 N,N-bis-(4-methoxyphenyl)-1,2-diphenylethane-1,2-diamine 
• 1236874-98-8 2,2,2-trifluoro-N-(4-iodophenyl)ethanethioamide 
• 3526-49-6 N-(4-iodophenyl)benzylamine 
• 3866-73-7 8-iodo-9b-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 
• 143874-19-5 (3R,4S)-1-(4-Iodo-phenyl)-3,4-diphenyl-azetidin-2-one 
• 76086-98-1 3-[(4-Iodo-phenylamino)-phenyl-methyl]-1,3-dihydro-indol-2-one 
• 52807-29-1 N-(4-iodophenyl)benzamide 
• 76086-78-7 1-phenyl-3-methyl-4-<(4-iodophenylamino)phenyl>methyl-5-pyrazolone 
• 144271-83-0 2-(chloromercurio)-4-iodo-N-(benzylidene)aniline 
• 31920-02-2 NbCl₅*C₆H₅CHNC₆H₄I 
• 1167444-70-3 1-(4-iodophenyl)-2,3,5-triphenyl-1-H-pyrrole 
• 1159386-90-9 N-(4-iodophenyl)-N-(2-methylene-1-phenylbut-3-en-1-yl)amine 

Relevant articles and documents

Lanthanides Mediated Oxidative Cross Coupling of Benzylalcohol and Various Amines to Form Corresponding Imines

Herein, a new and efficient approach towards the oxidative cross-coupling of benzylalcohol and various aromatic amines to form corresponding imines with high degree conversion (>80 %) and chemo-selectivity using lanthanide salts as pre-catalysts is presented. The catalyzed oxidative cross-coupling reaction using La(NO3)3·6H2O as pre-catalyst displayed a broad substrate scope. The reaction afforded various substituted imines from the reaction of benzylalcohol with ample variety of amines in good yields.

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)

The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

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

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.

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Retraction: Harnessing Thiol as a Benzyl Reagent for Photocatalytic Reductive Benzylation of Imines (Organic Letters DOI: 10.1021/2Facs.orglett.0c00065)

The authors retract this article after finding in subsequent studies that the quality of the purchased catalysts has a notable impact on the reproducibility of the results. Accordingly, the authors note that additional work is necessary to understand the

Metal-Free Ring Opening Cyclization of Cyclopropane Carbaldehydes and N-Benzyl Anilines: An Eco-Friendly Access to Functionalized Benzo[b]azepine Derivatives

Herein, we report a p-toluenesulfonic acid (PTSA) initiated mild and user-friendly ring opening/domino ring opening cyclization reaction (depends on substituent present in N-benzyl aniline) of cyclopropane carbaldehyde and N-benzyl aniline towards the formation of substituted 4-amino butanal/2,3-dihydro-1H-benzo[b]azepine. The product dihydro-1H-benzo[b]azepine was also converted into the corresponding tetrahydro-1H-benzo[b]azepine. (Figure presented.).

Mild and efficient synthesis of secondary aromatic amines by one-pot stepwise reductive amination of arylaldehydes with nitroarenes promoted by reusable nickel nanoparticles

The one-pot stepwise reductive amination of arylaldehydes with nitroarenes is described, using reusable nickel nanoparticles (Ni-pol) as catalyst and NaBH4 as mild, inexpensive, and safe reducing agent. The proposed catalytic system holds several advantages such as the use of a non-precious and earth-abundant metal, the facile separation of the catalyst from the reaction mixture by centrifugation, excellent stability towards air and moisture, very mild reaction conditions, good recyclability, broad substrate scope with good to excellent yields, and easy scalability (up to 1.0 g). FESEM analyses indicate that the active species are cubic nanocrystals of Ni in the average cross section value of 35 nm with a quite narrow (25–45 nm) and monomodal distribution, which becomes bimodal with the recycling reactions but without agglomeration.

Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant

A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.