102727-62-8

Upstream product

• 492-98-8 2,2'-biimidazole 
• 100-44-7 benzyl chloride 
• 4238-71-5 1-benzylimidazole 
• 100-39-0 benzyl bromide 
• 3581-91-7 4,5-Dimethylthiazole 
• 288-32-4 1H-imidazole 

Downstream Products

• 1616685-79-0 C₂₀H₁₈N₄*C₆F₃I₃ 

Relevant academic research and scientific papers

Reactions of C-imidazolyllithium derivatives with Group Ib compounds: tris3,C2)>tri-gold(I) and -silver(I). Crystal structure of bis (1-benzylimidazolin-2-yliden)gold(I) chloride

Upon reaction of LMX (M=Au, X=Cl, L=PPh3 or Me2S; M=Ag, X=NO3, L=Me2S) with 1-R-2-lithiumimidazole the lithium is replaced by a noble metal to give the species (1-R-2-M-imidazole)n (M=Au, R=methyl or benzyl, n=3; M=Ag, R=benzyl).From Me2SCuBr the compound bis(1-R-imidazol-2-yl) was obtained (R=methyl or benzyl).The unexpected formation during work up of , a carbene derivative, was confirmed by an X-ray crystal structural study which showed the presence of two independent molecules where C-Au-C is 175.2(4) or 176.6(4) deg, average Au-C is 2.027(7) Angstroem, and there is an Au...Au interaction at 3.2630(5) Angstroem.

Regioselective symmetrical bromination of protected 2,2′-biimidazole

Treatment of the benzyl and (trimethylsilylethoxymethyl) SEM protected 2,2′-biimidazoles, 2a and 2b, with 2 equivalents of N-bromosuccinimide (NBS) allows obtaining the 5,5′-dibromo and 4,4′-dibromo substituted biimidazoles, 3a and 5b respectively. The use of 4 equivalents of NBS, followed by treatment of the corresponding tetrabromoderivatives 4a and 5b with butyl lithium (BuLi), yields the 4,4′-dibromoderivatives 5a (G=Bn) and 5b (G=SEM).

Molecular electrostatic potential dependent selectivity of hydrogen bonding

A series of co-crystallizations between four biimidazole based compounds (1,1′-bis(pyridin-4-ylmethyl)-2,2′-biimidazole A1, 1,1′-bis(pyridin-3-ylmethyl)-2,2′-biimidazole A2, 1,1′-bis(pyridin-2-ylmethyl)-2,2′-biimidazole A3 and 1,1′-dibenzyl-2,2′-biimidazole A4) and nine symmetric aliphatic di-acids were carried out in order to determine if a ranking based on calculated molecular electrostatic potential surfaces (MEPS) can be used to effectively assign selectivity in hydrogen-bond based intermolecular interactions. Acceptors A1-A3 are asymmetric ditopic acceptors where two types of nitrogen atoms (pyridine and imidazole) are present, while A4 is a control molecule with only one type of acceptor to rule out any influence of steric factors in the observed structures. 28 of 36 experiments (78% yield) produced a co-crystal, as indicated by relevant changes in the corresponding infrared spectra. Twelve crystal structures of co-crystals of A1-A3 were obtained and every single one displayed primary OH...N hydrogens bonds that could be rationalized using the ranking based upon electrostatic potential maps. One crystal structure of A4 was obtained the result of which indicate that the patterns of behaviour established in this family of compounds is not a result of sterics or crystal packing; a simple electrostatic view of hydrogen-bond strength provides a reliable tool for predicting the most likely interactions in a competitive system.

Practical crystal engineering using halogen bonding: A hierarchy based on calculated molecular electrostatic potential surfaces

A series of co-crystallization experiments were performed using four multi-topic N-heterocyclic acceptor molecules and nine aromatic halogen-bond donors in order to establish how effectively a ranking of bond strength based on calculated molecular electrostatic potential surfaces translates into predictable primary interactions in the solid state. A total of ten new crystal structures were obtained, and in each case, the observed interaction took place between the best acceptor (with the larger negative electrostatic potential) on the N-heterocycle and the halogen-bond donor. The supramolecular yield (number of successful co-crystallizations) is 70% for iodine-donors whereas none of the bromo-substituted donors produced a co-crystal which underscores the importance of the magnitude of the electrostatic potential and of the polarizability of the halogen-bond donor in the context of successful practical crystal engineering.

Efficient synthesis of biazoles by aerobic oxidative homocoupling of azoles catalyzed by a copper(i)/2-pyridonate catalytic system

A highly efficient and convenient CuCl/2-pyridonate catalytic system for oxidative homocoupling of azoles affording a biazole product has been developed. With this system, a variety of biazoles have been effectively synthesized in good to excellent yields

An efficient and convenient Cu(OAc)2/air mediated oxidative coupling of azoles via C-H activation

An efficient and convenient approach to construct C-C bonds at the 2-position of azoles via Cu(OAc)2/air mediated oxidative homo- and cross-coupling reaction was reported. The corresponding products were obtained in good to excellent yield.

A One Step Synthesis of 4-Substituted Imidazoles. An Important Observation When N-Alkylating Imidazoles

Imidazoles substituted in the 2-position with methyl, 1e, phenyl, 1a, 2-imidazole, 1b-d, or t-butyldiphenylsilyl, 1f, react with soft electrophiles 2 to give modest yields of 4(5)-C-alkylated-imidazoles 3 and N-alkylated products 5.These two products are readily separated by flash chromatography.