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1077-18-5

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1077-18-5 Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 145, 1979 DOI: 10.1021/jo01315a035

Check Digit Verification of cas no

The CAS Registry Mumber 1077-18-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 7 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1077-18:
(6*1)+(5*0)+(4*7)+(3*7)+(2*1)+(1*8)=65
65 % 10 = 5
So 1077-18-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H15N/c1-2-3-9-12-10-11-7-5-4-6-8-11/h4-8,10H,2-3,9H2,1H3/b12-10+

1077-18-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name N-butyl-1-phenylmethanimine

1.2 Other means of identification

Product number -
Other names benzylidenebutylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1077-18-5 SDS

1077-18-5Relevant articles and documents

Organic reactions catalyzed by methylrhenium trioxide: Reactions of ethyl diazoacetate and organic azides

Zhu, Zuolin,Espenson, James H.

, p. 9901 - 9907 (1996)

Methylrhenium trioxide (CH3ReO3 or MTO) catalyzes several classes of reactions of ethyl diazoacetate, EDA. It is the first high valent oxo complex for carbene transfer. Under mild conditions and in the absence of other substrates, EDA was converted to a 9:1 mixture of diethyl maleate and diethyl fumarate. In the presence of alcohols, α-alkoxy ethyl acetates were obtained in good yield. The yields dropped for the larger and more branched alcohols, the balance of material being diethyl maleate and fumarate. An electron-donating group in the para position of phenols favors the formation of α-phenoxy ethyl acetates. The use of EDA to form α-thio ethyl acetates and N-substituted glycine ethyl esters, on the other hand, is hardly affected by the size or structure of the parent thiol or amine, with all of these reactions proceeding in high yield. MTO-catalyzed cycloaddition reactions occur between EDA and aromatic imines, olefins, and carbonyl compounds. Three-membered ring products are formed: aziridines, cyclopropanes, and epoxides, respectively. The reactions favor the formation of trans products, and provide a convenient route for the preparation of aziridines. Intermediate carbenoid and nitrenoid species have been proposed. In the presence of an oxygen source such as an epoxide, ethyl diazoacetate and azibenzil are converted to an oxalic acid monoethyl ester and tobenzil; at the same time the epoxide was converted to an olefin. These results provide further support for the proposed intermediate, a cyclic species containing Re, O, and CHCO2Et (or, occasionally, CPhC(O)Ph)in a three-membered ring.

Crystal phase effect of iron oxides on the aerobic oxidative coupling of alcohols and amines under mild conditions: A combined experimental and theoretical study

Geng, Longlong,Jian, Wei,Jing, Pei,Zhang, Wenxiang,Yan,Bai, Fu-Quan,Liu, Gang

, p. 145 - 152 (2019)

Selective catalytic oxidation using air as the terminal oxidant is an ecofriendly route for the synthesis of fine and commodity chemicals. However, the catalyst generally faces the challenges of the inertness of molecular oxygen, limited substrate scope, poor selectivity, and high cost. Moreover, the toxicity of the catalyst should also be considered when the products are used in pharmaceutical or biotechnological areas. Here, upon investigating the dependence of catalytic oxidation on the crystal phases of iron oxides, we find that naked γ-Fe2O3 particles exhibit excellent catalytic activity, selectivity, and stability in a series of imine synthetic reactions. The performance of γ-Fe2O3 particles is significantly better than that of α-Fe2O3 and Fe3O4 under mild reaction conditions, and the γ-Fe2O3 catalyst can be separated from the reaction mixture magnetically. Both experimental and theoretical calculation results show that γ-Fe2O3 possesses supercapability for oxygen activation. The inverse spinel structure of γ-Fe2O3 has abundant cation vacancies, which confers unique electronic properties on surface Fe species. These Fe species tend to transfer electrons to molecular oxygen to form O2? or O22? species. These oxygen species are favorable for the dehydrogenation of alcohols, which is responsible for the high activity of γ-Fe2O3 in this coupling reaction.

Silica functionalized Cu(II) acetylacetonate Schiff base complex: An efficient catalyst for the oxidative condensation reaction of benzyl alcohol with amines

Anbarasu,Malathy,Karthikeyan,Rajavel

, p. 305 - 312 (2017)

Silica functionalized Cu(II) acetylacetonate Schiff base complex via the one pot reaction of silica functionalized 3-aminopropyltriethoxysilane with acetyl acetone and copper acetate has been reported. The synthesized material was well characterized by analytical techniques such as FT-IR, UV-DRS, XRD, SEM-EDX, HR-TEM, EPR, ICP-AES and BET analysis. The characterization results confirmed the grafting of Cu(II) Schiff base complex on the silica surface. The catalytic activity of synthesized silica functionalized Cu(II) acetylacetonate Schiff base complex was evaluated through the oxidative condensation reaction of benzyl alcohol to imine.

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Ebara,N.

, p. 1151 - 1158 (1961)

-

A visible-light-responsive metal-organic framework for highly efficient and selective photocatalytic oxidation of amines and reduction of nitroaromatics

Chen, Peiqi,Guo, Zhifen,Liu, Xin,Lv, Hui,Che, Yan,Bai, Rong,Chi, Yanhong,Xing, Hongzhu

, p. 27074 - 27080 (2019)

Photocatalysis is a green synthetic method for organics transformation. We present here the synthesis of a novel visible-light-responsive metal-organic framework and its photocatalytic application. The prepared MOF is highly efficient for the self-coupling of primary amines and oxidative dehydrogenation of secondary amines to selectively produce imines assisted by the green and economic oxidant of molecular oxygen. Studies reveal that both energy transfer and electron transfer from the photoexcited MOF to molecular oxygen are important for amine oxidation, where the highly reactive species of superoxide radicals and singlet oxygen together account for the high catalytic performance. The photogenerated electrons of the MOF have also been utilized for the reduction of aromatic nitroarenes. Results show that they are highly selective for the reduction of nitroarenes to produce anilines in the presence of hydrazine hydrate. The work demonstrates the enormous potential of photoactive MOFs for converting organic substrates into valuable chemicals.

Reaction of Thioaldehydes with Amines

Okuma, Kentaro,Komiya, Yasuo,Ohta, Hiroshi

, p. 2402 - 2406 (1991)

The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.

Nitrogen-coordinated cobalt nanocrystals for oxidative dehydrogenation and hydrogenation of N-heterocycles

Wu, Yue,Chen, Zheng,Cheong, Weng-Chon,Zhang, Chao,Zheng, Lirong,Yan, Wensheng,Yu, Rong,Chen, Chen,Li, Yadong

, p. 5345 - 5352 (2019)

To endow non-noble metals with the high catalytic activity that is typically exhibited by noble metals is the central yet challenging aim for substituting noble metals. In this regard, by exploiting the coordination effect of nitrogen, we prepared cobalt nanocrystals stabilized by nitrogen-doped graphitized carbon (Co NCs/N-C). The obtained Co NC/N-C catalyst showed extraordinary performances toward both oxidative dehydrogenation of N-heterocycles and its reverse hydrogenation process under extremely mild conditions. A nearly quantitative conversion could be achieved for oxidative dehydrogenation even at room temperature (25 °C), for which the coordination effect of nitrogen is responsible: the interaction of Co-N induces a partial positive charge on the Co surface, thereby promoting the reaction. In contrast, cobalt nanocrystals supported by pristine carbon (Co NCs/C) proved to be inactive for oxidative dehydrogenation, owing to the lack of nitrogen. Moreover, in Co NCs/N-C, the N-doped graphitized carbon formed a protective layer for Co NCs, which preserved the active valence of Co species and prevented the catalyst from leaching. It was found that the catalyst still retained its excellent catalytic activity after five regeneration cycles; in comparison, its cobaltous oxide counterpart (CoOx/N-C) was barely active. As for the mechanism, electron paramagnetic resonance (EPR) analysis revealed the formation of superoxide anion radicals during the dehydrogenation process. Interestingly, the pressure of feed hydrogen had little effect on the hydrogenation process. Our Co NC/N-C catalyst is capable of activating molecular oxygen and hydrogen as effectively as noble metals; the coordination effect of nitrogen and the protection by the carbon layer in combination confer tremendous potential on the Co NCs/N-C for substituting noble-metal-based catalysts and soluble catalysts for homogeneous reactions.

CeO2 nanorods anchored on mesoporous carbon as an efficient catalyst for imine synthesis

Geng, Longlong,Song, Jinling,Zhou, Yahui,Xie, Yan,Huang, Jiahui,Zhang, Wenxiang,Peng, Luming,Liu, Gang

, p. 13495 - 13498 (2016)

CeO2 nanorods anchored on mesoporous carbon exhibit high activity and stability in aerobic oxidative coupling of alcohols and amines to imines. The abundant surface Ce3+ and the suitable interaction between CeO2 nanorods and the carbon support should be responsible for the excellent catalytic behaviors.

A mild and catalytic decarboxylation of α-iminoacids by tributyl phosphine

Barton, Derek H. R.,Taran, Frederic

, p. 4777 - 4780 (1998)

α-Iminoacids, prepared from α-keto acids and primary amines, undergo decarboxylation to the corresponding imines by reaction with a catalytic amount of tributylphosphine. No reaction has been observed with α-keto acids or their phenyl-hydrazone, tosyl-hydrazone or oxime derivatives under the same conditions. However, carboxy-azines react rapidly with tributylphosphine and give the corresponding aldazines quantitatively. The mechanism of this reaction is also discussed.

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Stein,Day

, p. 2569,2572 (1942)

-

New trans dichloro (triphenylphosphine)platinum(II) complexes containing N-(butyl),N-(arylmethyl)amino ligands: Synthesis, cytotoxicity and mechanism of action

Dalla Via, Lisa,García-Argáez, Aída Nelly,Agostinelli, Enzo,Belli Dell'Amico, Daniela,Labella, Luca,Samaritani, Simona

, p. 2929 - 2937 (2016)

Some new platinum(II) complexes have been prepared, of general formula trans-[PtCl2(PPh3){NH(Bu)CH2Ar}], where the dimension of the Ar residue in the secondary amines has been varied from small phenyl to large pyrenyl group. The obtained complexes, tested in vitro towards a panel of human tumor cell lines showed an interesting antiproliferative effect on both cisplatin-sensitive and -resistant cells. For the most cytotoxic derivative 2a the investigation on the mechanism of action highlighted the ability to induce apoptosis on resistant cells and interestingly, to inhibit the catalytic activity of topoisomerase II.

Expanding Coefficient: A Parameter to Assess the Stability of Induced-Fit Complexes

Talotta, Carmen,Concilio, Gerardo,De Rosa, Margherita,Soriente, Annunziata,Gaeta, Carmine,Rescifina, Antonio,Ballester, Pablo,Neri, Placido

supporting information, p. 1804 - 1808 (2021/03/08)

Here we propose a new parameter, the Expanding Coefficient (EC), that can be correlated with the thermodynamic stability of supramolecular complexes governed by weak secondary interactions and obeying the induced-fit model. The EC values show a good linear relationship with the log Kapp of the respective pseudorotaxane complexes investigated. According to Cram's Principle of Preorganization, the EC can be considered an approximate mechanical measure of the host's reorganization energy cost upon adopting the final bound geometry.

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω-Amino Fatty Acids under Hydrosilylation Conditions

Tongdee, Satawat,Wei, Duo,Wu, Jiajun,Netkaew, Chakkrit,Darcel, Christophe

, p. 5536 - 5539 (2021/08/07)

An efficient method for the preparation of lactams from ω-amino fatty acids under hydrosilylation is described. A variety of lactams such as pyrrolidinones, piperidinones and 2-azepanones were selectively synthesised in moderate to excellent yields (29 examples, up to 95 % isolated yields) with a good functional group tolerance. Notably, no metallic based catalyst was required to perform this transformation.

Fe2Mn(μ3-O)(COO)6 Cluster Based Stable MOF for Oxidative Coupling of Amines via Heterometallic Synergy

Wang, Ying-Xia,Wang, Hui-Min,Meng, Pan,Song, Dong-Xia,Qi, Zhikai,Zhang, Xian-Ming

supporting information, p. 2983 - 2989 (2021/08/30)

The direct catalytic oxidative coupling of amines is one of the attracting methods for the synthesis of a variety of pharmaceutical or industrial needed imines. Numerous earth-abundant manganese based salts, oxides, and complexes have been applied in this reaction. However, these compounds suffered from difficult separation, large catalyst loading, complicated reactivation or indeterminate activity. Considering the facts that metal-organic frameworks (MOFs) with crystalline structure, precise composition, and enormous surface area have superior performance in heterogeneous catalytic reactions, herein, we introduced Mn into [Fe3(μ3-O)(CH3COO)6], one of the precursors for the preparation of stable MOFs, and got [Fe2Mn(μ3-O)(CH3COO)6] cluster. After ligand replacement with biphenyl-3,4’,5-tricarboxylic acid (BPTC), heterometallic cluster-based [Fe2Mn(μ3-O)(BPTC)2(DMF)2(H2O)] (1) was obtained. As expected, 1 is stable and able to catalyze the homo- or cross-coupling of amines effectively and selectively with 0.9 mol% catalyst loading at room temperature. Control experiments indicated that the catalytic activity of 1 mainly stems from Mn sites and that Fe synergistically contributes to the stability. Additionally, 1 is recyclable and can be reused easily for at least 8 runs without obvious decrease in catalytic ability. To our knowledge, 1 should be the first heterometallic cluster-based MOF with defined structure suitable for the synthesis of diverse imines from oxidative coupling of amines under mild conditions, which may shed light on the easy preparation of effective heterogeneous catalysts for organic synthesis.

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