74367-81-0Relevant articles and documents
Direct cycle between co-product and reactant: An approach to improve the atom economy and its application in the synthesis and protection of primary amines
Guan, Qi,Jiang, Mingyang,Wu, Junhui,Zhai, Yanpeng,Wu, Yue,Bao, Kai,Zhang, Weige
supporting information, p. 5794 - 5799 (2016/11/06)
Two important goals of green chemistry are to maximize the efficiency of reactants and to minimize the production of waste. In this study, a novel approach to improve the atom economy of a chemical process was developed by incorporating a direct cycle between a co-product and a reactant of the same reaction. To demonstrate this concept, recoverable 3,4-diphenylmaleic anhydride (1) was designed and used for the atom-economical synthesis of aliphatic primary amines from aqueous ammonia. In each individual cycle, only ammonia and alkyl halide were consumed, and 1 was recovered in nearly a quantitative yield. In this approach for developing atom-economical protecting agents, 1 showed good performance as a recoverable protecting agent for primary amines. The broad substrate scope, good tolerance to various reaction conditions, and high reaction and recovery rates make 1 a valuable complement to conventional primary amine protecting agents.
High graphite N content in nitrogen-doped graphene as an efficient metal-free catalyst for reduction of nitroarenes in water
Yang, Fan,Chi, Cheng,Wang, Chunxia,Wang, Ying,Li, Yongfeng
supporting information, p. 4254 - 4262 (2016/08/02)
Four kinds of nitrogen-doped graphene (NG) as metal-free catalysts are synthesized by a one-step hydrothermal reaction and thermal treatment using graphene oxide and urea as precursors. It is found that the reduction of nitroarenes can be catalyzed by using a low NG loading and a small amount of NaBH4 in water with high yield. The type of nitrogen species in NG has an important effect on the reduction reaction. The NG catalyst containing the most graphite N shows the highest catalytic activity during reduction of nitroarenes, which demonstrates that the graphite N of NG plays a key role in impelling this reaction. The reaction mechanism is proven by GC-MS experiments, and DFT calculations reveal the reasons for the graphite N showing better catalytic activity. It is worth noting that no dehalogenation phenomenon occurs during the reduction process for halogen-substituted nitroarenes in contrast to conventional metal catalysts. In addition, the NG catalyst can be simply recycled and efficiently used for eight consecutive runs with no significant decrease in activity.
Weak halogen bonding in solid haloanilinium halides probed directly via chlorine-35, bromine-81, and iodine-127 NMR spectroscopy
Attrell, Robert J.,Widdifield, Cory M.,Korobkov, Ilia,Bryce, David L.
experimental part, p. 1641 - 1653 (2012/06/30)
A series of monohaloanilinium halides exhibiting weak halogen bonding (XB) has been prepared and characterized by 35Cl, 81Br, and 127I solid-state nuclear magnetic resonance (SSNMR) spectroscopy in magnetic fields of up to 21.1 T. The quadrupolar and chemical shift (CS) tensor parameters for halide ions (Cl-, Br-, I-) which act as electron density donors in the halogen bonds of these compounds are measured to provide insight into the possible relationship between halogen bonding and NMR observables. The NMR data for certain series of related compounds are strongly indicative of when such compounds pack in the same space group, thus providing practical structural information. Careful interpretation of the NMR data in the context of novel and previously available X-ray crystallographic data, and new gauge-including projector-augmented-wave density functional theory (GIPAW DFT) calculations has revealed several notable trends. When a series of related compounds pack in the same space group, it has been possible to interpret trends in the NMR data in terms of the strength of the halogen bond. For example, in isostructural series, the halide quadrupolar coupling constant was found to increase as the halogen bond weakens. In the case of a series of haloanilinium bromides, the 81Br isotropic chemical shift and CS tensor span both decrease as the bromide-halogen XB is weakened. These trends were reproduced using both GIPAW DFT and cluster-model calculations of the bromide ion magnetic shielding tensor. Such trends are particularly exciting given the well-known role that NMR has played historically in the characterization of hydrogen bonding.
Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes
De Noronha, Rita G.,Romao, Carlos C.,Fernandes, Ana C.
supporting information; experimental part, p. 6960 - 6964 (2010/03/03)
(Chemical Equation Presented) The reduction of aromatic nitro compounds to the corresponding amines with silanes catalyzed by high valent oxo-rhenium complexes is reported. The catalytic systems PhMe2SiH/ReIO 2(PPh3)2 (5 mol %) and PhMe2SiH/ ReOCl3(PPh3)2 (5 mol %) reduced efficiently a series of aromatic nitro compounds in the presence of a wide range of functional groups such as ester, halo, amide, sulfone, lactone, and benzyl. This methodology also allowed the regioselective reduction of dinitrobenzenes to the corresponding nitroanilines and the reduction of an aromatic nitro group in presence of an aliphatic nitro group. 2009 American Chemical Society.
Preparation and characterisation of iodo-functionalised azobenzene derivatives of the type I-p-C6H4-N=N-p-C6H 4-X
Siemeling, Ulrich,Bruhn, Clemens,Meier, Mario,Schirrmacher, Christian
experimental part, p. 1395 - 1401 (2009/06/20)
A broad range of azobenzene derivates of the general type I-p-C 6H4-N=N-p-C6H4-X (1) have been prepared. In the case of X = Ph (b), C≡C-Fc (e, Fc = ferrocenyl), OMe (g), Oi-Pr (i), and NMe2 (m), these compounds have been characterised by single-crystal X-ray structure analysis. In addition, the closely related 4-dimethylamino-1-(4-iodophenylazo)naphthalene 2 and 8-(4-iodophenylazo) quinoline 3 have also been prepared. Furthermore, the ferrocene derivative Fc-C≡C-p-C6H4-NH2 (4), which served as a starting material for the synthesis of I-p-C6H4-N=N-p- C6H4-C6H4C≡C-Fc (Ie), was prepared and structurally characterised by X-ray diffraction.
Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
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, (2008/06/13)
The invention presents a biguanide derivative or its salt expressed by a formula: STR1 (where R1 and R2 are as defined in Specification), or formula: STR2 (where A and R3 is as defined in specification). This biguanide derivative or its salt is preferably used as the effective amount of a disinfectant for humans, animals, medical appliances, etc.