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102-05-6 Usage

General Description

Dibenzylmethylamine is a tertiary amine with a distinctive odor and is commonly used as a precursor in organic synthesis reactions. Dibenzylmethylamine's versatile chemical properties make it valuable in various applications, including pharmaceuticals and chemical research, where it can act as a catalyst or a building block for the synthesis of more complex organic molecules. Its structure and reactivity make it a valuable component in the development of a wide range of chemical compounds and intermediates.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 3038, 1973 DOI: 10.1021/ja00790a064Tetrahedron Letters, 20, p. 3395, 1979 DOI: 10.1016/S0040-4039(01)95418-8

Check Digit Verification of cas no

The CAS Registry Mumber 102-05-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 102-05:
(5*1)+(4*0)+(3*2)+(2*0)+(1*5)=16
16 % 10 = 6
So 102-05-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H17N/c1-16(12-14-8-4-2-5-9-14)13-15-10-6-3-7-11-15/h2-11H,12-13H2,1H3

102-05-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name DIBEMETHINE

1.2 Other means of identification

Product number -
Other names METHYL DIBENZYLAMINE

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:102-05-6 SDS

102-05-6Relevant articles and documents

Enhancing the Catalytic Properties of Ruthenium Nanoparticle-SILP Catalysts by Dilution with Iron

Luska, Kylie L.,Bordet, Alexis,Tricard, Simon,Sinev, Ilya,Grünert, Wolfgang,Chaudret, Bruno,Leitner, Walter

, p. 3719 - 3726 (2016)

The partial replacement of ruthenium by iron ("dilution") provided enhanced catalytic activities and selectivities for bimetallic iron-ruthenium nanoparticles immobilized on a supported ionic liquid phase (FeRuNPs@SILP). An organometallic synthetic approach to the preparation of FeRuNPs@SILP allowed for a controlled and flexible incorporation of Fe into bimetallic FeRu NPs. The hydrogenation of substituted aromatic substrates using bimetallic FeRuNPs@SILP showed high catalytic activities and selectivities for the reduction of a variety of unsaturated moieties without saturation of the aromatic ring. The formation of a bimetallic phase not only leads to an enhanced differentiation of the hydrogenation selectivity, but even reversed the order of functional group hydrogenation in certain cases. In particular, bimetallic FeRuNPs@SILP (Fe:Ru = 25:75) were found to exhibit accelerated reaction rates for C=O hydrogenation within furan-based substrates which were >4 times faster than monometallic RuNPs@SILP. Thus, the controlled incorporation of the non-noble metal into the bimetallic phase provided novel catalytic properties that could not be obtained using either of the monometallic catalysts.

Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination

Moulin, Solenne,Dentel, Helene,Pagnoux-Ozherelyeva, Anastassiya,Gaillard, Sylvain,Poater, Albert,Cavallo, Luigi,Lohier, Jean-Francois,Renaud, Jean-Luc

, p. 17881 - 17890 (2013)

Reductive amination under hydrogen pressure is a valuable process in organic chemistry to access amine derivatives from aldehydes or ketones. Knoelker's complex has been shown to be an efficient iron catalyst in this reaction. To determine the influence of the substituents on the cyclopentadienone ancillary ligand, a series of modified Knoelker's complexes was synthesised and fully characterised. These complexes were also transformed into their analogous acetonitrile iron-dicarbonyl complexes. Catalytic activities of these complexes were evaluated and compared in a model reaction. The scope of this reaction is also reported. For mechanistic insights, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Festival of amination: Two series of modified Knoelker's complexes were synthesised and applied in the reductive amination of various carbonyl derivatives with primary or secondary amines (see scheme, TIPS = triisopropylsilyl). For a mechanistic insight, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Copyright

Synthesis of Amines via Carbon-Sulfur Bond Cleavages of Substituted Aminomethyl Sulfides with Organolithium Reagents: Aminocarbene Route to Enamines and Sterically Hindered Amines

Eisch, John J.,McNulty, John F.,Shi, Xian

, p. 7 - 9 (1994)

N-Substituted and N,N-disubstituted aminomethyl sulfides can be converted into secondary and tertiary amines, respectively, by organolithium reagents in high yields, regardless of whether the N-substituent is alkyl or aryl; for the former case, imines, and for the latter case, aminocarbenes, are the most likely intermediates.

Fluorocarbon accelerated supported transformations (FAST) on REM resin

Morphy,Rankovic, Zoran,York, Mark

, p. 7509 - 7511 (2001)

The use of perfluorous organic solvents in the solid-phase synthesis of 3° amines on REM resin allows a large reduction in both reaction time and the amount of amine required for a successful Michael reaction. Yields of products were typically at least three fold greater than those observed with standard solvents under the same conditions.

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Pine,Sanchez

, p. 829 (1971)

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A new method for generation of non-stabilized α-amino-substituted carbanions by the reaction of magnesium carbenoids with N-lithio arylamines: their reactivity and a new synthesis of α-amino acid derivatives

Satoh, Tsuyoshi,Osawa, Atsushi,Ohbayashi, Tohru,Kondo, Atsushi

, p. 7892 - 7901 (2006)

Magnesium carbenoids were generated from aryl 1-chloroalkyl sulfoxides with i-PrMgCl in THF at low temperature in quantitative yields. The magnesium carbenoids were found to be reactive with N-lithio alkylamines to afford an olefin, which was derived from dimerization of the magnesium carbenoid, in moderate yield. On the other hand, reaction of the magnesium carbenoids with N-substituted N-lithio arylamines gave non-stabilized α-amino-substituted carbanions in good yields. Reactivity of the α-amino-substituted carbanions with some electrophiles was investigated and it was found that ethyl chloroformate reacted to give α-amino acid derivatives in good yields. As a whole, a new method for one-pot, three-component combined synthesis of α-amino acid derivatives from aryl 1-chloroalkyl sulfoxides was realized.

Alcohol amination with heterogeneous ruthenium hydroxyapatite catalysts

Peeters, Annelies,Claes, Laurens,Geukens, Inge,Stassen, Ivo,De Vos, Dirk

, p. 191 - 197 (2014)

The intermolecular amination of alcohols was performed with ruthenium (Ru3+) immobilized on a calcium hydroxyapatite support. No additional base additives were necessary, nor did the catalyst require base treatment prior to reaction. High conversions were obtained with different amine and alcohol reactants.

Reductive amination without an external hydrogen source

Chusov, Denis,List, Benjamin

, p. 5199 - 5201 (2014)

A method of reductive amination without an external hydrogen source is reported. Carbon monoxide is used as the reductant. The reaction proceeds efficiently for a variety of carbonyl compounds and amines at low catalyst loadings and is mechanistically interesting as it does not seem to involve molecular hydrogen. Look, no H2! Reductive amination without an external hydrogen source has been developed using carbon monoxide as the reductant and rhodium acetate (0.2-1mol %) as catalyst. The method tolerates a variety of functional groups and provides target amines in good to excellent yields.

Reusable supported ruthenium catalysts for the alkylation of amines by using primary alcohols

Peishan, Siah,Dang, Tuan Thanh,Seayad, Abdul Majeed,Ramalingam, Balamurugan

, p. 808 - 814 (2014)

Efficient and recyclable ruthenium catalysts were synthesized from readily available polystyrene-or silica-supported phosphine ligands. Catalysts bound to the polymer support through an ether linkage showed good to excellent activity towards the N-alkylation of primary and secondary amines to afford the alkylated products in 62-99 % yield at 120-140°C. The supported phosphine ligand/ruthenium ratio was found to be crucial for higher catalytic activity and lower ruthenium leaching. The continuous flow N-alkylation of amines was demonstrated by using the supported catalyst in a column reactor. By adopting the hydrogen-borrowing strategy, the synthesis of the anti-Parkinson agent Piribedil was established in 98 % yield at 140°C. Support group steals the show: An efficient Ru-based heterogeneous catalyst from readily available supported phosphine ligands is developed. The nature of the linkage and the extent of ruthenium incorporation are crucial in determining the catalytic activity. The catalyst can be recycled and used under continuous flow in a packed-bed reactor. The alkylation of cyclic amines is achieved in excellent yield at moderate temperatures in the absence of any external base.

-

Snyder et al.

, p. 1301,1304 (1954)

-

Ruthenium-catalyzed reductive methylation of imines using carbon dioxide and molecular hydrogen

Beydoun, Kassem,Ghattas, Ghazi,Thenert, Katharina,Klankermayer, Jürgen,Leitner, Walter

, p. 11010 - 11014 (2015)

The use of the well-defined [Ru(triphos)(tmm)] catalyst, CO2 as C1 source, and H2 as reducing agent enabled the reductive methylation of isolated imines, as well as the direct coupling of amines with aldehydes and the subsequent reductive methylation of the insitu formed imines. The method, which afforded the corresponding N-methyl amines in very good to excellent yields, was also used for the preparation of the antifungal agent butenafine in one step with no apparent waste, thus increasing the atom efficiency of its synthesis.

Hydrosilylative Reduction of Tertiary Amides to Amines Catalyzed by N-(Phosphinoaryl)anilido Complexes of Iron and Cobalt

Hale, Dylan J.,Murphy, Luke J.,McDonald, Robert,Ferguson, Michael J.,Turculet, Laura

, p. 3818 - 3827 (2019)

The synthesis and structural characterization of low-coordinate Fe(II) and Co(II) complexes supported by the monoanionic P,N-ligand N-(2-dicyclohexylphosphinophenyl)-2,6-diisopropylanilide are described. A three-coordinate (P,N)Fe-hexamethyldisilazide complex (2), and four-coordinate (P,N)Fe- (3-Fe) and (P,N)Co-alkyl (3-Co) complexes were evaluated as pre-catalysts for the hydrosilylative reduction of amides with PhSiH3 (5 mol % pre-catalyst, 1 equiv. PhSiH3, 80 °C, 1–24 h). The Fe complex 2 proved to be more broadly effective for the reduction of a variety of tertiary amide substrates, and was shown to mediate the reduction of N,N-dibenzylbenzamide at a loading of 1 mol %, to achieve near quantitative formation of tribenzylamine in 1 h (80 °C). Complex 2 also proved effective for the hydrosilylation of tertiary amides under ambient conditions (5 mol % Fe, 24 h), which is a unique example of room temperature amide hydrosilylation mediated by an Fe catalyst without the need for photochemical activation. Given the widespread use of amide reduction protocols in synthesis, the development of efficient Fe-based catalysts that operate under mild conditions is an important target.

Expanding the Ligand Framework Diversity of Carbodicarbenes and Direct Detection of Boron Activation in the Methylation of Amines with CO2

Chen, Wen-Ching,Shen, Jiun-Shian,Jurca, Titel,Peng, Chun-Jung,Lin, Yen-Hsu,Wang, Yi-Ping,Shih, Wei-Chih,Yap, Glenn P. A.,Ong, Tiow-Gan

, p. 15207 - 15212 (2015)

A simple and convergent synthetic strategy used to increase the diversity of the carbodicarbene ligand framework through incorporation of unsymmetrical pendant groups is reported. Structural analysis and spectroscopic studies of ligands and their Rh complexes are reported. Reactivity studies reveal carbodicarbenes as competent organocatalysts for amine methylation using CO2 as a synthon. A unique B-H-activated boron-carbodicarbene complex was isolated as a reaction intermediate, providing mechanistic insight into the CO2 functionalization process.

Water-Soluble Iridium N-Heterocyclic Carbene Complexes for the Alkylation of Amines with Alcohols

Fernandes, Ana,Royo, Beatriz

, p. 3912 - 3917 (2017)

A new series of water-soluble Ir complexes with N-heterocyclic carbene ligands that bear ester and amide groups has been obtained and fully characterized. The new complexes are highly reactive and selective for the alkylation of amines with alcohols with a 1:1 ratio of reactants in water and in the absence of base or other additives. The catalytic system has a broad substrate scope, which allows the synthesis of a variety of primary and secondary amines in excellent yields. A tolerance to a large range of functional groups was obtained.

Titanium(IV) Isopropoxide and Sodium Borohydride: A Reagent of Choice for Reductive Amination

Bhattacharyya, Sukanta

, p. 2401 - 2404 (1994)

The preliminary results on the novel use of titanium(IV) isopropoxide and sodium borohydride in reductive amination reactions are reported.A highly efficient and mild procedure for reductive aminations of formaldehyde with a variety of primary and secondary amines is described.

Preparation of (aminomethyl)stannanes by reduction of α-amidoorgano stannanes

Burchat, Andrew F.,Chong, J. Michael,Nielsen, Nathan

, p. 7627 - 7630 (1996)

-

Metal-free reduction of secondary and tertiary N-phenyl amides by tris(pentafluorophenyl)boron-catalyzed hydrosilylation

Chadwick, Ryan C.,Kardelis, Vladimir,Lim, Philip,Adronov, Alex

, p. 7728 - 7733 (2014)

Tris(pentafluorophenyl)boron B(C6F5)3 is an effective catalyst for the hydrosilylative reduction of tertiary and N-phenyl secondary amides. It allows for the mild reduction of a variety of these amides in near quantitative yield, with minimal purification, at low temperatures, and with short reaction times. This reduction shows functional group tolerance for alkenes, nitro groups, and aryl halides, including aryl iodides.

Carbon Dioxide Reduction to Methylamines under Metal-Free Conditions

Blondiaux, Enguerrand,Pouessel, Jacky,Cantat, Thibault

, p. 12186 - 12190 (2014)

The first metal-free catalysts are reported for the methylation of amines with carbon dioxide. Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new methodology enables the methylation of N-H bonds in a wide variety of amines, including secondary amines, with increased chemoselectivity. Organocatalysis: Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new method makes possible the methylation of N-H bonds in a wide variety of amines, including secondary amines (see picture), with increased chemoselectivity.

Biomass-derived N-doped porous carbon: An efficient metal-free catalyst for methylation of amines with CO2

Tang, Feiying,Wang, Liqiang,Liu, You-Nian

, p. 6252 - 6257 (2019)

Developing green, efficient, and low-cost catalysts for methylation of N-H by using CO2 as the C1 resource is highly desired yet remains a significant challenge. Herein, N-doped porous carbons (NPCs) were designed, synthesized, and proved to be an excellent metal-free catalyst for CO2-participated methylation conversion. NPCs were prepared via the pyrolysis of a mixture of tannic acid and urea. Both theoretical calculation and experiment demonstrate that the N species especially pyridinic N and pyrrolic N within NPCs can work as Lewis basic sites for attacking CO2 to weaken the CO bonds and lower the molecule conversion barrier, facilitating the subsequent methylation of N-H to produce, for example, N,N-dimethylaniline. Besides, the unique porous structure can enrich CO2 and accelerate mass transfer, synergistically promoting the conversion of CO2. The optimized NPC(1/5) catalyst, integrating the porous structure and strong Lewis basicity, exhibits excellent catalytic activity for CO2-based methylation reaction under mild conditions (1 bar CO2, 75 °C). Our work, for the first time, demonstrates the feasibility of using NPCs to catalyze the methylation of amino compounds to produce N,N-dimethylamine by exploiting CO2 as the C1 resource.

Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol

Ai, Yao,Chen, Xiaozhong,Li, Feng,Liu, Peng,Yang, Chenchen,Yang, Jiazhi

, p. 325 - 334 (2021/10/07)

A Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand was designed, synthesized, and found to be a general and efficient auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol as both hydrogen source and methylating reagent. In the presence of [Cp*Ir(2,2′-CH2BiBzImH2)Cl][Cl], a range of desirable products were obtained in high yields with nearly complete selectivities. The reaction is highly attractive due to the highly atom economy, and minimal consumption of chemicals and energy. Notably, this research exhibits new potential of metal–ligand bifunctional catalysts for the activation of methanol as C1 source for organic synthesis.

Method for catalyzing hydrodesulfurization of thioamide derivative

-

Paragraph 0059-0063, (2021/07/09)

The invention provides a method for catalyzing hydrodesulfurization of a thioamide derivative, which comprises the following steps: sequentially adding a pentacarbonyl manganese bromide catalyst, a reaction substrate thioamide derivative, Lewis acid, a solvent and alkali into a polytetrafluoroethylene lined reaction tube, putting the reaction tube into a high-pressure kettle, introducing hydrogen to carry out catalytic hydrogenation reaction, cooling to room temperature, discharging gas, washing the reaction tube with ethyl acetate, passing through a silica gel small short column, carrying out spin drying, and carrying out column chromatography purification to obtain a target product. The monovalent manganese which is low in toxicity and good in chemical selectivity and biocompatibility is used as the catalyst to catalyze hydrodesulfurization of the thioamide derivative, the substrate range is wide, the yield of amine is high, and the method has high drug synthesis application value.

Iron-catalyzed chemoselective hydride transfer reactions

Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc

supporting information, (2021/06/07)

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

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