54116-98-2

Usage

Category

Organic compound

Structure

Guanidine derivative with a nitrogen atom connected to two carbon atoms and a lone pair of electrons

Uses

a. Reagent in organic synthesis
b. Catalyst in polymerization reactions
c. Blowing agent in polyurethane foam production
d. Production of rubbers, plastics, and adhesives

Safety

Relatively safe with low potential for acute toxicity

Potential side effects

Prolonged exposure may cause skin irritation and allergic reactions in some individuals

Upstream product

• 506-68-3 bromocyane 
• 106-49-0 p-toluidine 
• 624-31-7 4-tolyl iodide 
• 506-93-4 guanidine nitrate 
• 106-38-7 para-bromotoluene 
• 540-23-8 p-toluidine hydrochloride 
• 10532-64-6 N-(4-methylphenyl)cyanamide 
• 92114-96-0 mercury fulminate 

Downstream Products

• 1550369-58-8 1-(p-tolyl)-2-(p-tolylamino)-1H-benzo[d]imidazol-6-ol 
• 103-89-9 4-Methylacetanilide 

Relevant academic research and scientific papers

Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation

Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of PdII/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of PdII species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that PdII/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.

Reaction of quinones and guanidine derivatives: Simple access to bis-2-aminobenzimidazole moiety of benzosceptrin and other benzazole motifs

A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1′,2′:4,5]imidazo[1,2-a] pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.

Synthesis of symmetrical and unsymmetrical N, N ′-diaryl guanidines via copper/N-methylglycine-catalyzed arylation of guanidine nitrate

CuI/N-methylglycine-catalyzed coupling reaction of guanidine nitrate with both aryl iodides and bromides takes place at 70-100 °C, affording symmetrical N,N′-diaryl guanidines with good to excellent yields. Unsymmetrical N,N′-diaryl guanidines can be assembled via monoarylation of guanidine nitrate with aryl iodides bearing a strong electron-withdrawing group and subsequent coupling with another aryl iodide.

Copper-catalyzed guanidinylation of aryl iodides: The formation of N,N′-disubstituted guanidines

Chemical Equation Presented A copper-catalyzed cross-coupling reaction of guanidine nitrate with aryl iodides was used for the formation of N,N′-disubstituted guanidines to be used as potential therapeutics for strokes. A relatively inexpensive commercially available guanidine salt and a series of aryl iodides together with copper iodide and N,N-diethylsalicylamide as an efficient catalyst/1 igand system provided a simple diarylation procedure.

Synthesis and Structure-Activity Studies of N,N'-Diarylguanidine Derivatives. N-(1-Naphthyl)-N'-(3-ethylphenyl)-N'-methylguanidine: A New, Selective Noncompetitive NMDA Receptor Antagonist

Diarylguanidines, acting as NMDA receptor ion channel site ligands, represent a new class of potential neuroprotective drugs.Several diarylguanidines structurally related to N,N'-di-o-tolylguanidine (DTG), a known selective ? receptor ligand, were synthes

Synthesis and Structure-Activity Relationships of N,N'-Di-o-tolylguanidine Analogues, High-Affinity Ligands for the Haloperidol-Sensitive ? Receptor

With an eye toward the development of novel atypical antipsychotic agents, we have studied the structure-affinity relationships of N,N'-di-o-tolylguanidine (DTG, 3) and its congeners at the haloperidol-sensitive ? receptor.A number of DTG analogues were synthesized and evaluated in in vitro radioligand displacement experiments with guinea pig brain membrane homogenates, using the highly ?-specyfic radioligands -3 and -(+)-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine and the phencyclidine (PCP) receptor specyfic compounds -N-piperidine and -(+)-5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine.The affinity of N,N'-diarylguanidines for the ? receptor decreases with increasing steric bulk of ortho substituents larger than C2H5.Hydrophobic substituents are generally preferred over similarly positioned hydrophilic ones.Furthermore, electroneutral substituents are preferred over strongly electron donating or withdrawing groups.Significant binding to the ? receptor is usually retained as long as at least one side of the guanidine bears a preferred group (e.g. 2-CH3C6H5).Replacement of one or both aryl rings with certain saturated carbocycles (e.g. cyclohexyl, norbornyl, or adamantyl) leads to a significant increase in affinity.By combining the best aromatic and best saturated carbocyclic substituents in the same molecule, we arrived at some of the most potent ? ligands described to date (e.g.N-exo-2-norbornyl-N'-(2-iodophenyl)guanidine, IC50 = 3 nM vs -3).All of the compounds tested were several orders of magnitude more potent at the ? receptor than at the PCP receptor, with a few notable exceptions.This series of disubstituted guanidines may be of value in the development of potential antipsychotics and in the further pharmacological and biochemical chracterization of the ? receptor.

Bicyclic amidines

New amidine/isocyanate adducts are particularly useful as catalysts for hardening epoxy resins, in particular pulverulent coating compositions based on epoxy resins. New bicyclic amidines are excellent starting materials for manufacturing these amidine/isocyanate adducts.