110-18-9Relevant articles and documents
Copper(I) halide complexes with N,N′-diallyl-N,N,N′,N′- tetramethylethylenediaminium (L2+). Synthesis and crystal structures of the complexes [L0.5CuCl2], [L0.5CuCl 0.72Br1.28], and [L0.5CuBr2]
Monchak,Goreshnik,Mys'Kiv
, p. 143 - 148 (2011)
The Eschweiler-Clarke reaction of ethylenediamine with formaldehyde and formic acid yielded N,N,N′,N′-tetramethylethylenediamine, which was alkylated with allyl chloride or allyl bromide to give the corresponding N,N′-diallyl-N,N,N′,N′-tetramethylethylenediaminium (L 2+) dihalides. In methanolic solutions of copper(II) halide and an appropriate ligand, ac electrochemical synthesis with copper wire electrodes afforded single crystals of Cu(I) complexes with L2+: [L 0.5CuCl2] (I), [L0.5CuCl0.72Br 1.28] (II), and [L0.5CuBr2] (III). The crystal structures of complexes I-III were determined by X-ray diffraction study. The isostructural crystals of I and II are monoclinic, space group P21/n, Z = 4. For I: a = 7.632(4) A, b = 11.318(5) A, c = 10.635(5) A, β = 98.551(7)°, V = 908.4(7) A3. For II: a = 7.7415(7) A, b = 11.4652(9) A, c = 10.7267(10) A, β = 98.351(4)°, V = 942.0(2) A3. The organic cation L 2+ acts as a bridge linking a pair of separate cuprous halide fragments Cu2X4. Although being isostoichiometric with I and II, complex III has a different structure. The crystals of III are monoclinic, space group P21/c, a = 6.519(2) A, b = 9.060(3) A, c = 16.284(6) A, β = 97.219(4)°, V = 954.2(6) A3, Z = 4. In structure III, the inorganic fragment forms infinite polymer chains (CuBr 2 - ) n . The organic and inorganic parts are held together only by electrostatic interactions. Structures I-III are stabilized by hydrogen bonds (C)H...X (2.6-2.9 A).
Brown,Newton
, p. 1117,1118-1120 (1966)
Cleavable cationic antibacterial amphiphiles: Synthesis, mechanism of action, and cytotoxicities
Hoque, Jiaul,Akkapeddi, Padma,Yarlagadda, Venkateswarlu,Uppu, Divakara S. S. M.,Kumar, Pratik,Haldar, Jayanta
, p. 12225 - 12234 (2012)
The development of novel antimicrobial agents having high selectivity toward bacterial cells over mammalian cells is urgently required to curb the widespread emergence of infectious diseases caused by pathogenic bacteria. Toward this end, we have developed a set of cationic dimeric amphiphiles (bearing cleavable amide linkages between the headgroup and the hydrocarbon tail with different methylene spacers) that showed high antibacterial activity against human pathogenic bacteria (Escherichia coli and Staphylococcus aureus) and low cytotoxicity. The Minimum Inhibitory Concentrations (MIC) were found to be very low for the dimeric amphiphiles and were lower or comparable to the monomeric counterpart. In the case of dimeric amphiphiles, MIC was found to decrease with the increase in the spacer chain length (n = 2 to 6) and again to increase at higher spacer length (n > 6). It was found that the compound with six methylene spacers was the most active among all of the amphiphiles (MICs = 10-13 μM). By fluorescence spectroscopy, fluorescence microscopy, and field-emission scanning electron microscopy (FESEM), it was revealed that these cationic amphiphiles interact with the negatively charged bacterial cell membrane and disrupt the membrane integrity, thus killing the bacteria. All of the cationic amphiphiles showed low hemolytic activity (HC50) and high selectivity against both gram-positive and gram-negative bacteria. The most active amphiphile (n = 6) had a 10-13-fold higher HC50 than did the MIC. Also, this amphiphile did not show any cytotoxicity against mammalian cells (HeLa cells) even at a concentration above the MIC (20 μM). The critical micellar concentration (CMC) values of gemini surfactants were found to be very low (CMC = 0.30-0.11 mM) and were 10-27 times smaller than the corresponding monomeric analogue (CMC = 2.9 mM). Chemical hydrolysis and thermogravimetric analysis (TGA) proved that these amphiphiles are quite stable under both acidic and thermal conditions. Collectively, these properties make the newly synthesized amphiphiles potentially superior disinfectants and antiseptics for various biomedical and biotechnological applications.
Modulation spectroscopy. Kinetics for the self-reactions of some α-aminoalkyl radicals in solution
Marriott, Paul R.,Castelhano, Arlindo L.,Griller, David
, p. 274 - 278 (1982)
The optical spectra and reaction kinetics of some α-aminoalkyl radicals, RCHN(CH2R)2; R = H, Me, Ph, were measured in solution using the technique of modulation spectroscopy.These radicals undergo diffusion controlled self-reaction with rate constants ca. 109 M-1 s-1.When R=Ph, the absorption spectrum has a well defined maximum at 346 nm; ε = 3390 M-1 cm-1, while the spectra when R = H or Me were less intense (ε346nm ca. 500 M-1 cm-1) and tailed into the visible.These spectra are substantially red-shifted when compared with those of simple alkyl radicals, an effect which is thought to be due to the interaction between the unpaired electron and the lone pair of electrons on nitrogen.
Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8]-dodecane (TATD) towards some reducing agents: Synthesis of TMEDA
Rivera, Augusto,Rios-Motta, Jaime
, p. 1471 - 1481 (2007)
N,N,N′,N′-Tetramethylethylenediamine (TMEDA) can be synthesized by simple reduction of 1,3,6,8-tetraazatricyclo-[4.4.1.1.3,8] dodecane (TATD), an aminal cage type amine, with formic acid. The aminal can be converted to TMEDA in high yield very easily and in a very short time. We comment on the scope and limitations of the reduction of this aminal and propose a possible reaction mechanism.
COMPLEXES OF 9-PROPYLFLUORENYL ION PAIRS WITH TERTIARY POLYAMINES IN APOLAR SOLVENTS
Helary, G.,Lefevre-Jenot, L.,Fontanille, M.,Smid, J.
, p. 139 - 146 (1981)
The complexation of tetramethylethylenediamine (TMEDA), hexamethyltriethylenetetramine (HMTT) and tetramethyltetraazacyclotetradecane (TMTCT) with ion pairs of 9-(n-propyl)fluorenyllithium (PFl-, Li+) and n-butyl-9-(n-propyl)fluorenylmagnesium (BuPFlMg) in cyclohexane was studied by optical spectroscopy.The results can be explained in terms of externally complexed tight ion pairs and ligand-separated ion pairs, the latter complexes being much less soluble.With HMTT and PFl-, Li+, the only complexes formed are (PFl-, Li+)2 HMTT (λm 357 nm) and PFl-, HMTT, Li+ (λm 383 nm).The reaction of PFl-, Li+, TMEDA with TMTCT to form the loose ion pair complex PFl-, TMTCT, Li+ has a rate constant in toluene of 250 M-1 sec-1.With the magnesium compound, the amines form only a loose ion pair complex, e.g., BuMg+, TMEDA, PFl- (λm 382 nm).
Ginmanini et al.
, p. 484,485, 487 (1976)
A METHOD FOR PREPARING ALKYLATED AMINES
-
Page/Page column 31; 32, (2021/09/11)
The present invention pertains to a method for preparing an alkylated amine by reacting a primary or secondary amine with an alcohol in the presence of hydrogen, a metal catalyst supported by photosensitive titanium oxide, and UV irradiation. Advantageously, the reaction can be carried out under mild reaction conditions.
Preparation method of tetramethylethylenediamine
-
Paragraph 0051-0067, (2020/08/02)
The invention discloses a preparation method of tetramethylethylenediamine, and the method comprises the following steps: adding a pyrrolidone series solvent and composite catalyst TZOH into an autoclave, covering the autoclave with an autoclave cover, carrying out nitrogen displacement, introducing acetylene, introducing dimethylamine after the temperature is stable, heating the autoclave to 70-120 DEG C, and keeping the temperature for 3-8 hours; after the heat preservation is finished, cooling, discharging the residual pressure into the pyrrolidone series solvent, applying to the next batch, filtering materials in the autoclave, and recovering a catalyst; and rectifying mother liquor to obtain the product tetramethylethylenediamine; according to the method, the tetramethylethylenediamine can be prepared, basically no waste water or waste residue is generated, excessive raw materials, solvents and catalysts can be recycled, the element utilization rate is high, and compared with theprior art that a large amount of formaldehyde-containing waste water or industrial waste salt is generated, the environment-friendly advantage is obvious.
