4172-91-2

Upstream product

• 920-68-3 heptamethyldisilazane 
• 622-44-6 phenylcarbonimidic dichloride 
• 20743-50-4 1-methyl-5-phenyltetrazole 
• 20743-49-1 2-methyl-5-phenyl-2H-tetrazole 
• 1455-91-0 1-phenyl-4-methyl-1,4-dihydro-5H-tetrazol-5-thione 
• 1007-36-9 1-methyl-3-phenylurea 
• 123149-88-2 1-Methyl-2,4-diphenyl-1,2,3-triazolium-chlorid 
• 593-75-9 methyl isocyanate 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 2724-69-8 1-methyl-3-phenylthiourea 
• 14213-16-2 5-methyl-1-phenyl-1H-tetrazole 
• 5378-52-9 phenyl-1H-tetrazole 
• 77-78-1 dimethyl sulfate 
• 5097-82-5 5-phenyl-1H-tetrazolone 

Downstream Products

• 69909-87-1 N-(2,4-dimethyl-3-phenylimino-[1,2,4]thiadiazolidin-5-ylidene)-N'-phenyl-benzamidine 
• 59541-67-2 N-cyano-N'-methyl-N''-phenyl-guanidine 
• 82561-32-8 O,S-dimethyl O-(trimethylsilyl) phosphorodithioate 
• 78077-91-5 2-Isopropyl-4-methyl-3,5-diphenylimino-1,2,4-oxadiazolidin 
• 1007-36-9 1-methyl-3-phenylurea 
• 112777-83-0 1-Methyl-3-(4-nitro-phenyl)-4-[(Z)-phenylimino]-[1,3]diazetidin-2-one 
• 112777-82-9 1-Methyl-3-phenyl-4-[(Z)-phenylimino]-[1,3]diazetidin-2-one 
• 106929-75-3 3-methyl-2,4-bis(phenylimino)-1,3-thiazetidine 
• 112777-81-8 1,3-Dimethyl-4-phenylimino-[1,3]diazetidin-2-one 
• 73027-62-0 N-methyl-1-phenyl-1H-tetrazol-5-amine 
• 1360895-56-2 (4-butylamino-1,6-dimethyl-1,3,5-triazin-2(1H)-ylidene)phenylamine 
• 1360895-69-7 (4-(4-methoxyphenyl)-1,6-dimethyl-1,3,5-triazin-2-ylidene)phenylamine 
• 1380583-37-8 C₁₁H₁₂N₂O 

Relevant academic research and scientific papers

Selective formation of formamidines, carbodiimides and formimidates from isocyanide complexes of Mn(i) mediated by Ag2O

The isocyanide ligands in complexes fac-[Mn(CNR)(bipy)(CO)3]+ are selectively transformed into formamidines, carbodiimides and formimidates upon nucleophilic addition of NH2Me or alkoxides and subsequent treatment with Ag

Direct Observation of an Imidoylnitrene: Photochemical Formation of PhC(=NMe)?N and Me?N from 1-Methyl-5-phenyltetrazole

The imidoylnitrene 8, N-methyl-C-phenylimidoylnitrene, has been generated by laser photolysis of 1-methyl-5-phenyltetrazole 6 at 5 K and characterized by its ESR spectrum (|D/hc|=0.9602, |E/hc|=0.0144 cm?1). In addition, the triplet excited sta

Nitrile imines and nitrile ylides: Rearrangements of benzonitrile N-methylimine and benzonitrile dimethylmethylide to azabutadienes, carbodiimides, and ketenimines. chemical activation in thermolysis of azirenes, tetrazoles, oxazolones, isoxazolones, and oxadiazolones

Flash vacuum thermolysis (FVT) of 1-methyl-5-phenyltetrazole (5b), 2-methyl-5-phenyltetrazole (1b), and 3-methyl-5-phenyl-1,3,4-oxadiazol-2(3H)-one (3b) affords the nitrile imine (2b), which rearranges in part to N-methyl-N′-phenylcarbodiimide (7b). Another part of 2b undergoes a 1,4-H shift to the diazabutadiene (13). 13 undergoes two chemically activated decompositions, to benzonitrile and CH2=NH and to styrene and N 2. FVT of 2,2-dimethyl-4-phenyl-oxazol-5(2H)-one (16) at 400 C yields 3-methyl-1-phenyl-2-azabutadiene (18) in high yield. In contrast, FVT of 3,3-dimethyl-2-phenyl-1-azirene (21) at 600 C or 4,4-dimethyl-3-phenyl- isoxazolone (20) at 600 C affords only a low yield of azabutadiene (18) due to chemically activated decomposition of 18 to styrene and acetonitrile. There are two reaction paths from azirene (21): one (path a) leading to nitrile ylide (17) and the major products styrene and acetonitrile and the other (path b) leading to the vinylnitrene (22) and ketenimine (23). The nitrile ylide PhC -=N+=C(CH3)2 (17) is implicated as the immediate precursor of azabutadiene (18). FVT of either 3-phenylisoxazol- 5(4H)one (25) or 2-phenylazirene (26) at 600 C affords N-phenylketenimine (28). The nitrile ylide PhC-=N+=CH2 (30) is postulated as a reversibly formed intermediate. N-Phenylketenimine (28) undergoes chemically activated free radical rearrangement to benzyl cyanide. The mechanistic interpretations are supported by calculations of the energies of key intermediates and transition states.

Nitrile imines: Matrix isolation, IR spectra, structures, and rearrangement to carbodiimides

The structures and reactivities of nitrile imines are subjects of continuing debate. Several nitrile imines were generated photochemically or thermally and investigated by IR spectroscopy in Ar matrices at cryogenic temperatures (Ph-CNN-H 6, Ph-CNN-CH317, Ph-CNN-SiMe323, Ph-CNN-Ph 29, Ph3C-CNN-CPh334, and the boryl-CNN-boryl derivative 39). The effect of substituents on the structures and IR absorptions of nitrile imines was investigated computationally at the B3LYP/6-31G level. IR spectra were analyzed in terms of calculated anharmonic vibrational spectra and were generally in very good agreement with the calculated spectra. Infrared spectra were found to reflect the structures of nitrile imines accurately. Nitrile imines with IR absorptions above 2200 cm -1 have essentially propargylic structures, possessing a CN triple bond (typically PhCNNSiMe323, PhCNNPh 29, and boryl-CNN-boryl 39). Nitrile imines with IR absorptions below ca. 2200 cm-1 are more likely to be allenic (e.g., HCNNH 1, PhCNNH 6, HCNNPh 43, PhCNNCH317, and Ph3C-CNN-CPh334). All nitrile imines isomerize to the corresponding carbodiimides both thermally and photochemically. Monosubstituted carbodiimides isomerize thermally to the corresponding cyanamides (e.g., Ph-N=C=N-H 5 Ph-NH-CN 8), which are therefore the thermal end products for nitrile imines of the types RCNNH and HCNNR. This tautomerization is reversible under flash vacuum thermolysis conditions.

A versatile thiouronium-based solid-phase synthesis of 1,3,5-triazines

A thiouronium-based solidphase synthesis of a 1,3,5-triazine scaffold has been developed. The key feature of the synthesis is the use of a readily accessible solid-supported thiouronium salt as a primary precursor for the stepwise assembly of the 1,3,5-tri-azine substrate. The sulfur linker employed in the synthesis is stable under both acidic and basic conditions and is versatile enough to provide access to monocyclic, bicyclic, and spirocyclic compounds with the 1,3,5-triazine scaffold. By using this synthetic strategy, a representative set of 79 compounds containing the 1,3,5-triazine scaffold were prepared.

Clean photodecomposition of 1-methyl-4-phenyl-1 H-tetrazole-5(4 H)-thiones to carbodiimides proceeds via a biradical

The photochemistry of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione (1a) and 1-(3-methoxyphenyl)-4-methyl-1H-tetrazole-5(4H)-thione (1b) was studied in acetonitrile at 254 and 300 nm, which involves expulsion of dinitrogen and sulfur to form the respective carbodiimides 5a,b as sole photoproducts. Photolysis of the title compounds in the presence of 1,4-cyclohexadiene trap led to the formation of respective thioureas, providing strong evidence for the intermediacy of a 1,3-biradical formed by the loss of dinitrogen. In contrast, a trapping experiment with cyclohexene provided no evidence to support an alternative pathway of photodecomposition involving initial desulfurization followed by loss of dinitrogen via the intermediacy of a carbene. Triplet sensitization and triplet quenching studies argue against the involvement of a triplet excited state. While the quantum yields for the formation of the carbodiimides 5a,b were modest and showed little change on going from a C 6H5 (1a) to mOMeC6H4 (1b) substituent on the tetrazolethione ring, the highly clean photodecomposition of these compounds to a photostable end product makes them promising lead structures for industrial, agricultural, and medicinal applications.

One-pot syntheses of 5-amino-1-aryltetrazole derivatives

A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed. Georg Thieme Verlag Stuttgart.

Preparation of N,N'-bis(aryl)guanidines from electron deficient amines via masked carbodiimides

Preparation of N,N'-bis(aryl)guanidines by alkylation of electron deficient amines with trityl protected carbodiimides is described. Also reported is a method for the dehydration of N-trityl-N'-aryl ureas to the corresponding carbodiimides using the Burge

A mild and efficient preparation of carbodiimides

Mono and diaryl carbodiimides were prepared in high yield under mild conditions by treating a thiourea with methanesulfonyl chloride in the presence of triethylamine and DMAP.