16596-05-7

Basic information

• Product Name: N,N'-Bis(2,6-dimethylphenyl)formamidine
• Synonyms: N,N'-Bis(2,6-dimethylphenyl)formamidine;N1,N2-Bis(2,6-dimethylphenyl)formamidine;N1,N2-Bis(2,6-xylyl)formamidine
• CAS NO: 16596-05-7
• Molecular Formula: C₁₇H₂₀N₂
• Molecular Weight: 252.35
• Mol File: 16596-05-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N'-Bis(2,6-dimethylphenyl)formamidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(2,6-dimethylphenyl)formamidine(16596-05-7)
• EPA Substance Registry System: N,N'-Bis(2,6-dimethylphenyl)formamidine(16596-05-7)

Safety Data

• Hazardous Substances Data: 16596-05-7(Hazardous Substances Data)

Upstream product

• 61110-94-9 1,3-bis(2,6-dimethyl phenyl)carbodiimide 
• 25480-78-8 N,N′-bis(2,6-dimethylphenyl)thiourea 
• 122-51-0 orthoformic acid triethyl ester 
• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 1268158-36-6 1,3-bis(2,6-dimethylphenyl)-5-tert-butyl-6-oxo-6H-pyrimidinium-4-olate 
• 1337917-55-1 1,3-bis(2,6-dimethylphenyl)-3,4,5,6,7,8-hexahydro-1,3-diazocin-1-ium bromide 
• 1337917-68-6 C₂₂H₂₈N₂ 
• 1337917-57-3 1,3-bis(2,6-dimethylphenyl)-3,4,5,6,7,8-hexahydro-1,3-diazocin-1-ium tetrafluoroborate 
• 1596366-66-3 [HC(N-2,6-Me₂C₆H₃)2]2Y(CH₂SiMe₃)(THF) 
• 106316-57-8 tetrakis(tetrahydrofurane)diiodidoytterbium(II) 

Relevant articles and documents

Predicting molecular isomerism of symmetrical and unsymmetrical: N, N ′-diphenyl formamidines in the solid-state: Crystal structure, Hirshfeld surface analysis, pairwise interaction energy, and Δ H fusionand Δ S fusioncorrelations

Eight N,N′-diphenylformamidines with the general formula [N-(Ar),N′-(Ar′)] were synthesized and characterized using spectroscopic and analytical techniques. Four were symmetrical (Ar = Ar′) while the other four were unsymmetrical (Ar ≠ Ar′). Five of the c

N-Heterocyclic Carbene-Catalyzed Truce-Smiles Rearrangement of N-Arylacrylamides via the Cleavage of Unactivated C(aryl)-N Bonds

We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the

The p: K a values of N-aryl imidazolinium salts, their higher homologues, and formamidinium salts in dimethyl sulfoxide

A series of imidazolinium salts, their six-, seven- A nd eight-membered homologues, and the related formamidinium salts were prepared, and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each type of structural variation on the acidity of each salt was considered, particularly noting the importance of ring size and the effect of the steric and electronic nature of the N-aryl substituents. The effect of a cyclic structure was also probed through comparing the cyclic systems with the corresponding formamidinium salts, noting the importance of conformational flexibility in the latter cases. Along with allowing choice of appropriate bases for deprotonation of these species, it is anticipated that the data presented will aid in the understanding of the nucleophilicity, and potentially catalytic efficacy, of the corresponding carbenes.

Impact of Electronic and Steric Changes of Ligands on the Assembly, Stability, and Redox Activity of Cu4(μ4-S) Model Compounds of the CuZ Active Site of Nitrous Oxide Reductase (N2OR)

Model compounds have been widely utilized in understanding the structure and function of the unusual Cu4(μ4-S) active site (CuZ) of nitrous oxide reductase (N2OR). However, only a limited number of model compounds that mimic both structural and functional features of CuZ are available, limiting insights about CuZ that can be gained from model studies. Our aim has been to construct Cu4(μ4-S) clusters with tailored redox activity and chemical reactivity via modulating the ligand environment. Our synthetic approach uses dicopper(I) precursor complexes (Cu2L2) that assemble into a Cu4(μ4-S)L4 cluster with the addition of an appropriate sulfur source. Here, we summarize the features of the ligands L that stabilize precursor and Cu4(μ4-S) clusters, along with the alternative products that form with inappropriate ligands. The precursors are more likely to rearrange to Cu4(μ4-S) clusters when the Cu(I) ions are supported by bidentate ligands with 3-atom bridges, but steric and electronic features of the ligand also play crucial roles. Neutral phosphine donors have been found to stabilize Cu4(μ4-S) clusters in the 4Cu(I) oxidation state, while neutral nitrogen donors could not stabilize Cu4(μ4-S) clusters. Anionic formamidinate ligands have been found to stabilize Cu4(μ4-S) clusters in the 2Cu(I):2Cu(II) and 3Cu(I):1Cu(II) states, with both the formation of the dicopper(I) precursors and subsequent assembly of clusters being governed by the steric factor at the ortho positions of the N-aryl substituents. Phosphaamidinates, which combine a neutral phosphine donor and an anionic nitrogen donor in the same ligand, form multinuclear Cu(I) clusters unless the negative charge is valence-trapped on nitrogen, in which case the resulting dicopper precursor is unable to rearrange to a multinuclear cluster. Taken together, the results presented in this study provide design criteria for successful assembly of synthetic model clusters for the CuZ active site of N2OR, which should enable future insights into the chemical behavior of CuZ

Co(III) N,N′-diarylformamidine dithiocarbamate complexes: Synthesis, characterization, crystal structures and biological studies

Three symmetric N,N-diarylformamidine dithiocarbamates, N,N′-bis(2,6-dimethylphenyl)formamidine dithiocarbamate (DTL1), N,N′-bis(2,6-disopropylphenyl)formamidine dithiocarbamate (DTL2) and N,N′-dimesitylformamidine dithiocarbamate (DTL3), and three unsymm

Synthesis and structural studies of nickel(II)- and copper(II)-N,N′-diarylformamidine dithiocarbamate complexes as antimicrobial and antioxidant agents

A series of six N′N-diarylformamidine dithiocarbamate ligands and their metal complexes of Cu(II) and Ni(II) chloride salts have been synthesized. Three symmetrical, N,N′-bis(2,6-dimethylphenyl)formamidine dithiocarbamate (DL1), N,N′-bis(2,6-disopropylphe

Gold(I) Complexes Stabilized by Nine- and Ten-Membered N-Heterocyclic Carbene Ligands

Nine- and ten-membered N-heterocyclic carbene (NHC) ligands have been developed and for the first time their gold(I) complexes were synthesized. The protonated NHC pro-ligands 2 a–h were prepared by the reaction of readily available N,N′-diarylformamidines with bis-electrophilic building blocks, followed by anion exchange. In situ deprotonation of the tetrafluoroborates 2 a–h with tBuOK in the presence of AuCl(SMe2) provided fast access to NHC-gold(I) complexes 3–10. These new NHC-gold(I) complexes show very good catalytic activity in a cycloisomerization reaction (0.1 mol % catalyst loading, up to 100 % conversion) and their solid-state structures reveal high steric hindrance around the metal atom (%Vbur up to 53.0) which is caused by their expanded-ring architecture.

Zn(ii) and Cu(ii) formamidine complexes: Structural, kinetics and polymer tacticity studies in the ring-opening polymerization of ?-caprolactone and lactides

Treatment of N,N′-bis(2,6-dimethylphenyl)formamidine (L1), N,N′-bis(2,6-diisopropylphenyl)formamidine (L2), and N,N′-dimesitylformamidine (L3) with Zn(OAc)2·2H2O or Cu(OAc)2·H2O produced the corresponding Zn(ii)

Metal-free access of bulky: N, N ′-diarylcarbodiimides and their reduction: Bulky N, N ′-diarylformamidines

A metal-free synthesis of symmetrical and unsymmetrical bulky N,N′-diaryl carbodiimides from the dehydrosulfurisation of their corresponding N,N′-diarylthiourea with 4-dimethylaminopyridine (DMAP) and iodine under mild reaction conditions with moderate to excellent yields has been established. In the literature, the classical method of dehydrosulfurisation of bulky N,N′-diarylthiourea to N,N′-diarylcarbodiimide has been reported using toxic metal oxide (HgO) and magnesium sulphate (MgSO4) under harsh reaction conditions. Furthermore, easy access to 1,3-disubstituted symmetric and unsymmetrical N,N′-diaryl formamidines involving the reaction of symmetrical and unsymmetrical N,N′-diaryl carbodiimides with sodium borohydride is described. The widely used method for the preparation of bulky N,N′-diaryl formamidines is the treatment of primary amines with triethylorthoformate in the presence of acid under high temperature reaction conditions.

Synthesis and structural analysis of formamidinate-supported Mg complexes

Abstract Reactions of 2-mesitylmagnesium bromide with N,N′-diarylformamidines afforded five Mg compounds [(DPhF)Mg(THF)2]2(μ-Br)2 (1), [D(3,5-Xyl)F]2Mg(THF)2 (2), [D(2,6-Xyl)F]2Mg(THF) (3),