614-30-2

Basic information

• Product Name: N-METHYL-N-BENZYLANILINE
• Synonyms: METHYLBENZYLANILINE;n-methyl-n-phenyl-benzenemethanamin;N-methyl-N-phenyl-Benzenemethanamine;N-Methyl-N-benzylanilin;Benzylmethylphenylamine;N-Phenyl-N-methylbenzylamine;N-methyl-N-(phenylmethyl)aniline;N-METHYL-N-BENZYLANI
• CAS NO: 614-30-2
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.28
• EINECS: 210-375-4
• Product Categories: Intermediates of Dyes and Pigments;organic chemical
• Mol File: 614-30-2.mol

Chemical Properties

• Melting Point: 9.3°C
• Boiling Point: 318 °C(lit.)
• Flash Point: 110 °C
• Appearance: Clear yellow to amber liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000416mmHg at 25°C
• Refractive Index: n20/D 1.605(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.009g/l
• PKA: 4.38±0.50(Predicted)
• CAS DataBase Reference: N-METHYL-N-BENZYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-N-BENZYLANILINE(614-30-2)
• EPA Substance Registry System: N-METHYL-N-BENZYLANILINE(614-30-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 614-30-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-METHYL-N-BENZYLANILINE is used as a synthetic building block for the preparation of fused tetrahydroquinolines. These compounds are of significant interest in the pharmaceutical industry due to their potential therapeutic properties and applications in the development of new drugs.
Used in Chemical Synthesis:
N-METHYL-N-BENZYLANILINE is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows for a wide range of reactions, making it a versatile component in the synthesis of different chemical products.
Used in Research and Development:
N-METHYL-N-BENZYLANILINE is employed as a research compound in the field of organic chemistry. It is utilized in the development of new synthetic methods, the study of reaction mechanisms, and the exploration of novel chemical properties.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 2677, 1995 DOI: 10.1021/jo00114a014

InChI:InChI=1/C14H15N/c1-15(14-10-6-3-7-11-14)12-13-8-4-2-5-9-13/h2-11H,12H2,1H3

Upstream product

• 124-41-4 sodium methylate 
• 131916-59-1 N,N-dibenzyl-N-methyl-anilinium; iodide 
• 100-44-7 benzyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 65-85-0 benzoic acid 
• 50-00-0 formaldehyd 
• 758640-21-0 N-Benzylaniline 
• 13657-45-9 N-methyl-N-(methoxymethyl)-aniline 
• 101292-66-4 N-benzyl-N-phenyl-O-allylhydroxylamine 
• 75-24-1 trimethylaluminum 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 

Downstream Products

• 611-92-7 1,3-dimethyl-1,3-diphenylurea 
• 131719-59-0 4-(benzyl-methyl-amino)-benzyl alcohol 
• 16547-01-6 N-Benzyl-N-methylaniline N-oxide 
• 3784-37-0 4-(Methyl-benzyl-amino)-azobenzol 
• 18773-77-8 methyl(phenyl)cyanamide 
• 100-39-0 benzyl bromide 
• 25458-39-3 methylallylbenzylphenylammonium iodide 
• 1215-41-4 4-(benzyl(methyl)amino)benzaldehyde 
• 883-93-2 2-Phenylbenzothiazole 
• 104226-37-1 N-benzyl-N-methyl-4-nitroaniline 
• 100709-10-2 N-methyl-N-4-bromophenylbenzylamine 
• 6387-18-4 3-(N-methyl-anilinomethyl)-benzenesulfonic acid 
• 860681-12-5 2-[4-(benzyl-methyl-amino)-phenylsulfanyl]-benzoic acid benzenesulfonylamide 
• 25458-37-1 (+/-)-N-ethyl-N-benzyl-N-methyl-anilinium; iodide 

Relevant articles and documents

Iridium/graphene nanostructured catalyst for the: N -alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process

A facile iridium/graphene-catalyzed methodology providing an efficient synthetic route for C-N bond formation is reported. This catalyst can directly promote the formation of C-N bonds, without pre-activation steps, and without solvents, alkalis and other additives. This protocol provides a direct N-alkylation of amines using a variety of primary and secondary alcohols with good selectivity and excellent yields. Charmingly, the use of diols resulted in intermolecular cyclization of amines, and such products are privileged structures in biologically active compounds. Two examples illustrate the advantages of this catalyst in organic synthesis: the tandem catalysis to synthesize hydroxyzine, and the intermolecular cyclization to synthesize cyclizine. Water is the only by-product, which makes this catalytic process sustainable and environmentally friendly. This journal is

Hydroborative reduction of amides to amines mediated by La(CH2C6H4NMe2-: O)3

The deoxygenative reduction of amides to amines is a great challenge for resonance-stabilized carboxamide moieties, although this synthetic strategy is an attractive approach to access the corresponding amines. La(CH2C6H4NMe2-o)3, a simple and easily accessible lanthanide complex, was found to be highly efficient not only for secondary and tertiary amide reduction, but also for the most challenging primary reduction with pinacolborane. This protocol exhibited good tolerance for many functional groups and heteroatoms, and could be applied to gram-scale synthesis. The active species in this catalytic cycle was likely a lanthanide hydride.

Switching between mono and doubly reduced odd alternant hydrocarbon: designing a redox catalyst

Since the early Hückel molecular orbital (HMO) calculations in 1950, it has been well known that the odd alternant hydrocarbon (OAH), the phenalenyl (PLY) system, can exist in three redox states: closed shell cation (12π e?), mono-reduced open shell neutral radical (13π e?) and doubly reduced closed shell anion (14π e?). Switching from one redox state of PLY to another leads to a slight structural change owing to its low energy of disproportionation making the electron addition or removal process facile. To date, mono-reduced PLY based radicals have been extensively studied. However, the reactivity and application of doubly reduced PLY species have not been explored so far. In this work, we report the synthesis of the doubly reduced PLY species (14π e?) and its application towards the development of redox catalysisviaswitching with the mono-reduced form (13π e?) for aryl halide activation and functionalization under transition metal free conditions without any external stimuli such as heat, light or cathodic current supply.

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Synthesis of N-heterocyclic carbene-Pd(II)-5-phenyloxazole complexes and initial studies of their catalytic activity toward the Buchwald-Hartwig amination of aryl chlorides

Three new N-heterocyclic carbene (NHC)-Pd(II) complexes using 5-phenyloxazole as the ancillary ligand have been obtained in moderate to good yields by a one-pot reaction of the corresponding imidazolium salts, palladium chloride and 5-phenyloxazole under mild conditions. Initial studies showed that one of the complexes is an efficient catalyst for the Buchwald-Hartwig amination of aryl chlorides with various secondary and primary amines under the varied catalyst loading of 0.01-0.05 mol%, thus it will enrich the chemistry of NHCs and give an alternative catalyst for the coupling of challenging while cost-low aryl chlorides.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes

A catalyst-free, stereoselective visible-light-driven annulation reaction between alkenes and N,N-substituted dialkyl anilines for the synthesis of substituted tetrahydroquinolines is presented. The reaction is driven by the photoexcitation of an electron donor-acceptor (EDA) complex, and the resulting products are obtained in good to high yields with complete diastereoselectivity. Mechanistic rationale and photochemical characterization of the EDA-complex are provided.