13829-06-6

Basic information

• Product Name: TETRAMETHYLURONIUM CHLORIDE)
• Synonyms: TETRAMETHYLURONIUM CHLORIDE);Chloro-bis(dimethylamino)-methylium chloride;Methanaminium, chloro(dimethylamino)dimethyl-, chloride (1:1);2-Chloro-1，1，3，3-tetramethylformamidinium chloride
• CAS NO: 13829-06-6
• Molecular Formula: C₅H₁₂ClN₂*Cl
• Molecular Weight: 171.07
• Mol File: 13829-06-6.mol
• Article Data: 63

Chemical Properties

• Melting Point: 110-112 °C
• Appearance: /
• CAS DataBase Reference: TETRAMETHYLURONIUM CHLORIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYLURONIUM CHLORIDE)(13829-06-6)
• EPA Substance Registry System: TETRAMETHYLURONIUM CHLORIDE)(13829-06-6)

Safety Data

• Hazardous Substances Data: 13829-06-6(Hazardous Substances Data)

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 
• 75-44-5 phosgene 
• 632-22-4 tetramethylurea 
• 79-37-8 oxalyl dichloride 
• 57-13-6 urea 
• 14989-30-1 hypochloric acid 
• 2782-91-4 1,1,3,3-tetramethyl-2-thiourea 

Downstream Products

• 34959-67-6 C₁₁H₁₇N₂O₂P 
• 30482-34-9 4-(Dimethylamino-phenyl-methyl)-N,N-dimethyl-benzamide 
• 13880-55-2 N,N,N',N'-tetramethyl-C-phenylmethanediamine 
• 19111-89-8 Tetramethyldiamino-diphenyl-methan 
• 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 
• 77379-98-7 2,6-ditert-butyl-7,7-bis(dimethylamino)quinone methide 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 
• 125700-67-6 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 
• 94790-37-1 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 
• 129995-78-4 4--2-dimethylamino-5-methyl-6-phenylpyrimidine 

Relevant articles and documents

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.

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.

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.

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.

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.

Improved one-pot preparation of tetramethylfluoroformamtoinium hexafluorophosphate

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Copper Complexes of New Redox-Active 4,5-Bisguanidino-Substituted Benzodioxole Ligands: Control of the Electronic Structure by Counter-Ligands, Solvent, and Temperature

Herein, we analyze the possibility of controlling the electronic structure of mononuclear copper complexes featuring new redox-active 4,5-bisguanidino-substituted benzodioxole ligands. The nature of the guanidino groups, the anionic counter-ligands, the applied solvent (polarity), and the temperature are the parameters that decide if a CuIIcomplex with neutral ligand unit or a CuIcomplex with radical monocationic ligand unit is the adequate description. Under special conditions, a temperature-dependent equilibrium of the two valence tautomeric forms (CuII/neutral ligand and CuI/radical monocationic ligand) is achieved. Removal of a ligand-centered electron from a paramagnetic CuIIcomplex with a neutral ligand unit leads to a diamagnetic CuIcomplex with a dicationic ligand unit through a redox-induced electron-transfer (RIET) process.

4,4′,5,5′-tetrakis(guanidinyl)binaphthyl-synthesis and properties of two redox-active ligands and oxidative C-C coupling to perylene derivatives

We report the synthesis and properties of the new redox-active ligands 4,4′,5,5′-tetrakis(tetramethylguanidinyl)binaphthyl and 4,4′,5,5′-tetrakis(N,N′-dimethylethyleneguanidinyl)binaphthyl. The first dinuclear zinc complexes were prepared. Oxidative C-C coupling of these compounds leads to perylene derivatives.

Bidentate guanidine ligands with ethylene spacer in copper-dioxygen chemistry: Structural characterization of bis(μ-hydroxo) dicopper complexes

The syntheses of the aliphatic bidentate guanidine-amine-hybrid ligands DMEGdmae (L1), TMGdmae (L2), TMGdeae (L3) and DPipGdmae (L4) as well as the reaction of their Cu(I) complexes with molecular oxygen (monitored by UV-Vis spectroscopy) are reported. The molecular structures of 10 bis(μ-hydroxo) dicopper complexes based on these ligands are described. The solid state structures of [Cu2(μ-OH)2(DMEGdmae)2]X 2 (X- = I- (1), CF3SO 3- (2), SbF6- (3), PF 6- (4)), [Cu2(μ-OH)2(TMGdmae) 2]X2 (X- = I- (5), CF 3SO3- (6)), [Cu2(μ-OH) 2(TMGdeae)2]Cu2I4 (7) and [Cu 2(μ-OH)2(DPipGdmae)2]X2 (X - = CF3SO3- (8), SbF 6- (9), PF6- (10)) show a square-planar distorted coordination of the copper(II) ion. The bis(μ-hydroxo) dicopper complex 1 exhibits a Cu?Cu distance of 2.860(1) , which is one of the smallest observed for hydroxo-bridged copper compounds so far. The influence of the anion on the structure of the bis(μ-hydroxo) dicopper(II) unit is analyzed for the reported complexes and a literature overview with emphasis on the structural characteristics of the Cu2O2 moiety of bis(μ-hydroxo) dicopper(II) and bis(μ-oxo) dicopper(III) is given.

Investigation of a family of structurally-related guanidinium ionic liquids through XPS and thermal analysis

A family of structurally-related guanidinium bistriflimide ionic liquids has been prepared and characterized. TGA analyses showed a high thermal stability for all the proposed ionic liquids while DSC and XPS analyses divided them into distinct subsets depending on whether one or more constraining cycles were present. The results obtained highlighted the influence of the cation structure on some of the physico-chemical properties and thus the possibility to tune them by selecting proper substituents. The solvatochromic parameters of a selected guanidinium IL have also been studied.

Octamethylbiguanide perchlorate.

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Redox-Active Guanidines with One or Two Guanidino Groups and Their Integration in Low-Dimensional Perovskite Structures

Redox-active guanidines are versatile reagents in redox and proton-coupled electron-transfer (PCET) reactions. Recently, they were integrated as sacrificial electron donors for the prohibition of metal oxidation in perovskite materials. Herein we report t