13829-06-6

Usage

InChI:InChI=1/C5H12ClN2.ClH/c1-7(2)5(6)8(3)4;/h1-4H3;1H/q+1;/p-1

Upstream product

• 34656-65-0 Dimethyltrichloromethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 632-22-4 tetramethylurea 
• 75-44-5 phosgene 
• 2782-91-4 1,1,3,3-tetramethyl-2-thiourea 
• 79-37-8 oxalyl dichloride 
• 14989-30-1 hypochloric acid 
• 57-13-6 urea 

Downstream Products

• 72834-78-7 N''-Phenylacetyl-N,N,N',N'-tetramethylguanidin 
• 17951-14-3 2-(4'-nitrophenyl)-1,1,3,3-tetramethylguanidine 
• 72834-77-6 N''-(4-Methylbenzoyl)-N,N,N',N'-tetramethylguanidin 
• 27649-51-0 1,1-Bis-dimethylamino-2-cyan-2-<4-brom-phenyl>-aethylen 
• 442873-72-5 1,8-bis(tetramethylguanidino)naphthalene 
• 61-33-6 penicillin G 
• 1213750-68-5 1,1,3,3-tetramethyl-2-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)isouronium chloride 
• 655-05-0 2-(dimethylamino)-5-phenyloxazol-4(5H)-one 
• 1513-00-4 2-(dimethylamino)-5-(2-fluorophenyl)oxazol-4(5H)-one 
• 17159-28-3 2-(dimethylamino)-5-(4-methoxyphenyl)oxazol-4(5H)-one 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling reactions in aqueous microdroplets with catalytically active fluorous interfaces

Using microfluidic techniques and a novel fluorous-tagged palladium catalyst, we generated droplet reactors with catalytically active walls and used these compartments for small molecule synthesis.

Isotopic probing of molecular oxygen activation at copper(I) sites

Copper-dioxygen (CuO2) adducts are frequently proposed as intermediates in enzymes, yet their electronic and vibrational structures have not always been understood. [Cu(η1-O2)TMG 3tren]+ (TMG3-tren = 1,1,1-tris{2-[N 2-(1,1,3,3-tetramethylguanidino)]ethyl}amine) features end-on (η1) O2 coordination in the solid state. Described here is an investigation of the compound's solution properties by nuclear magnetic resonance spectroscopy, density functional calculations, and oxygen isotope effects. The study yields two major findings. First, [Cu(η1-O2)TMG3tren]+ is paramagnetic due to a triplet electronic structure; this is in contrast to other copper compounds where O2 is bound in a side-on manner. Second, the oxygen equilibrium isotope effect upon O2 binding to copper(I) ( 18O EIE = K(16O16O)/K(16O 18O) = 1.0148 ± 0.0012) is significantly larger than those determined for iron and cobalt η1-O2 adducts. This result is suggested to reflect greater ionic (CuII-O2 -I) character within the valence bond description. A revised interpretation of the physical origins of the 18O EIEs upon O 2 binding to redox metals is also advanced along with experimental data that should be used as benchmarks for interpreting 18O kinetic isotope effects upon enzyme reactions.

Bent and twisted: The electronic structure of 2-azapropenylium ions obtained by guanidine oxidation

New bis-2-azapropenylium ions are obtained by oxidation of guanidino-substituted aromatic compounds. The dications 12+ (1 = 1,4-bis-tetramethylguanidinobenzene) and 22+ (2 = 1,4-bis-guanidinobenzene) exhibit unexpected bent-twisted structures, that differ from the known 2-azapropenylium ion structures (linear-orthogonal 2-azaallenium ion or bent-planar 2-azaallylium ion), and resemble the structures of carbodicarbenes. Their electronic structure was analysed by a combination of experiments and quantum chemical calculations. The results indicate that the bent-planar structure is disfavoured for steric reasons, while the allene-type linear-orthogonal structure is also disfavoured due to the electron-donating groups that support the bent form. For these reasons a bent-twisted structure is adopted, in which the nitrogen atom is engaged with two different orbitals in π-bonding with the carbon π-system and in a weaker π-interaction with the CN2 group of the guanidino system.

A solvent having switchable hydrophilicity

A new kind of switchable solvent, a switchable-hydrophilicity solvent, is hydrophobic and has very low miscibility with water when in air but is hydrophilic and has complete miscibility with water when under an atmosphere of CO2. We report here the first example of such a solvent, N,N,N′-tributylpentanamidine. Solvents such as these could be used for the extraction of low-polarity organic products, such as vegetable oils, followed by the removal of the solvent from the product by carbonated water. Carbonated water is able to extract the solvent from the product because the CO2 converts the solvent to its hydrophilic form. The solvent can then be separated from the carbonated water upon removal of the CO2, because this removal triggers the conversion of the solvent back to its hydrophobic, water-immiscible form. Importantly, distillation is not required for removal of the solvent from the product.

Construction of copper chains with new fluorescent guanidino-functionalized naphthyridine ligands

The three new blue-fluorescent ligands 2,7-bis(tetramethylguanidino)-1,8-naphthyridine (1), 2,7-bis(N,N′-dimethylethylene-guanidino)-1,8-naphthyridine (2) and 2,7-bis(N,N′-diisopropylguanidino)-1,8-naphthyridine (3) are synthesized, and their optical properties (electronic absorption and emission spectroscopy) studied. Reactions of 1 or 2 with [Cu(CH3CN)4]BF4 yield the Cu4 chain compounds [Cu4(1)2](BF4)4 (that crystallizes as [Cu4(1)2(CH3CN)2](BF4)4·2CH2Cl2) and [Cu4(2)2](BF4)4. The variations of the optical properties upon coordination are evaluated, and the electronic transitions identified by time-dependent DFT (TD-DFT) calculations. Then the redox properties of the new Cu4 chain complexes are studied. In the course of these experiments, the new Cu6 complex [Cu4(1)2(CuCl2)2]2+, in which two CuCl2- units coordinate to the Cu4 chain in [Cu4(1)2]4+, was fully characterized. In addition, the Cu3 chain complexes [Cu3(1)3]3+ and [Cu3(1)2]3+ were isolated as products of redox-induced degradation processes. Finally, we show by quantum chemical calculations that in [M4(1)2]4+ complexes (M = coinage metal), the HOMO changes from a ligand-centered to a metal-centered orbital for replacement of M = Cu by Au.

A Convenient procedure for the preparation of bis(dialkylamino) malononitriles

N,N,N++,N++-Tetraalkylchloroformamidinium chlorides react with trimethylsilyl cyanide without solvent to give bis(dialkylamino) malononitriles, which can be distilled off from the reaction mixture in vacuo. Georg Thieme Verlag Stuttgart.

Complexes of manganese, iron, zinc, and molybdenum with a superbasic tris(guanidine) derivative of tris(2-ethylamino)amine (tren) as a tripod ligand

The synthesis of the novel tripod ligand N[CH2CH2N=C(NMe2)2]3, based on the tris(2-ethylamino)amine (tren) backbone and having a set of three superbasic tetramethylguanidine (TMG) donor atoms instead of the primary amine functionalities, is described. This ligand has been prepared by treating tren with the Vilsmeyer salt [(Me2N)2CCl]Cl in the presence of triethylamine as an auxiliary base and NaOH. Complexes of manganese(II), iron(II), and zinc(II) as biologically relevant transition metal ions as well as of molybdenum(0) have been synthesized and spectroscopically and structurally characterized. The electrochemical properties of selected complexes have been studied.

Trinuclear complexes and coordination polymers of redox-active guanidino-functionalized aromatic (GFA) compounds with a triphenylene core

Herein, we report on the synthesis, redox activity, and coo r d i n a t i o n c h e m i s t r y of 2, 3 , 6 , 7 , 1 0 , 1 1 - h e x a k i s - (tetramethylguanidino)triphenylene. CV measurements indicated that the new compound could be oxidized in three se

Spectroscopic capture and reactivity of S = 1/2 nickel(iii)-oxygen intermediates in the reaction of a NiII-salt with mCPBA

Ni(iii)-intermediates are trapped by EPR and UV/Vis spectroscopy in the reaction of a Ni(ii) salt with mCPBA. On the basis of their oxo-transfer and hydrogen-atom abstraction abilities the intermediates are assigned as the elusive terminal Ni(iii)-oxo/hydroxo species. The findings suggest that Ni(iii)-O(H) moieties are viable reactants in oxidation catalysis. The Royal Society of Chemistry 2012.

Probing the Proton-Coupled Electron-Transfer (PCET) Reactivity of a Cross-Conjugated Cruciform Chromophore by Redox-State-Dependent Fluorescence

Proton-coupled electron transfer (PCET) reactions are of great importance in synthetic chemistry and in biology, but the acquisition of kinetic information for these reactions is often difficult. Herein, we report the synthesis of a new PCET reagent, showing redox-state dependent fluorescence, by merging the concept of cross-conjugated cruciform chromophores with the strategy of imposing redox activity and Br?nsted basicity to aromatic compounds by substitution with guanidino groups. The compound is isolated and characterized in all stable states—reduced, twofold and fourfold protonated and twofold oxidized—and then applied in PCET reactions by using its redox-state dependent fluorescence signal for kinetic measurements.