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103-83-3 Usage

Chemical Properties

colourless to light yellow liquid with an amine odour

Uses

Different sources of media describe the Uses of 103-83-3 differently. You can refer to the following data:
1. Intermediate, especially for quaternary ammonium compounds; dehydrohalogenating catalyst; corrosion inhibitor; acid neutralizer; potting compounds; adhesives; cellulose modifier.
2. N,N-Dimethylbenzylamine is used in the preparation of bis[(N,N-dimethylamino)benzyl] selenide. It acts as a catalyst in the curing reaction of formulations of diglycidyl ether of bisphenol A and tetrahydrophthalic anhydride. It undergoes directed ortho metalation with butyl lithium. It reacts with methyl iodide to get ammonium salt, which is used as phase transfer catalysts. Further, it is used as a catalyst for the formation of polyurethane foams and epoxy resins.
3. N,N-Dimethylbenzylamine was used in the synthesis of bis[(N,N-dimethylamino)benzyl] selenide. It has been used as catalyst during curing reaction of formulations of diglycidyl ether of bisphenol A and tetrahydrophthalic anhydride.

Preparation

25% Aqueous Dimethylamine, 1088 grams Benzyl Chloride, 126.6 grams In the apparatus of Example 1, the benzyl chloride was added dropwise over a two-hour period to the amine (molar ratio 1 to 6) at a rate sufficient to maintain the temperature below 40°C. Stirring was continued at room temperature for an additional hour to insure completion of the reaction denoted by the equation below. Thereafter the reaction mixture was cooled in a separatory funnel while standing in a refrigerator maintained at 5° C. and separated into two layers. The upper oily layer, weighing 111.5g, was removed and steam distilled until no further oleaginous component was observed in the distillate as it came over. The crude distillate was found to contain 103.5g of N,N-dimethylbenzylamine (76.1% of theory), 3.3g of dimethylamine and no quaternary salts. The dimethylamine was distilled off below 29°C under atmospheric pressure from the N,N-dimethylbenzylamine (bp 82°C/18mmHg).

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 531, 1975 DOI: 10.1021/jo00892a043Synthetic Communications, 6, p. 539, 1976 DOI: 10.1080/00397917608063545

General Description

A colorless to light yellow liquid with an aromatic odor. Slightly less dense than water and slightly soluble in water. Flash point approximately 140°F. Corrosive to skin, eyes and mucous membranes. Slightly toxic by ingestion, skin absorption and inhalation. Used in the manufacture of adhesives and other chemicals.

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

N,N-Dimethylbenzylamine neutralizes acids on exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. May attack some plastics [USCG, 1999].

Health Hazard

Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomitting.

Fire Hazard

Special Hazards of Combustion Products: Toxic vapors are generated when heated.

Flammability and Explosibility

Flammable

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and skin contact. Corrosive. A severe eye and skin irritant. Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of NOx

Purification Methods

Dry the amine over KOH pellets and fractionate it over Zn dust in a CO2—free atmosphere. It has a pKa2 5 of 8.25 in 45% aqueous EtOH. Store it under N2 or in a vacuum. The picrate has m 94-95o, and the picrolonate has m 151o (from EtOH). [Skita & Keil Chem Ber 63 34 1930, Coleman J Am Chem Soc 55 3001 1933, Devereux et al. J Chem Soc 2845 1957.] The tetraphenyl borate salt has m 182-185o. [Crane Anal Chem 28 1794 1956, Beilstein 12 IV 2161.]

Check Digit Verification of cas no

The CAS Registry Mumber 103-83-3 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 3 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 103-83:
(5*1)+(4*0)+(3*3)+(2*8)+(1*3)=33
33 % 10 = 3
So 103-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3/p+1

103-83-3 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (D0688)  N,N-Dimethylbenzylamine  >98.0%(GC)

  • 103-83-3

  • 25mL

  • 125.00CNY

  • Detail
  • TCI America

  • (D0688)  N,N-Dimethylbenzylamine  >98.0%(GC)

  • 103-83-3

  • 500mL

  • 420.00CNY

  • Detail
  • Alfa Aesar

  • (A12191)  N-Benzyldimethylamine, 98+%   

  • 103-83-3

  • 250ml

  • 238.0CNY

  • Detail
  • Alfa Aesar

  • (A12191)  N-Benzyldimethylamine, 98+%   

  • 103-83-3

  • 1000ml

  • 499.0CNY

  • Detail
  • Alfa Aesar

  • (A12191)  N-Benzyldimethylamine, 98+%   

  • 103-83-3

  • 5000ml

  • 2411.0CNY

  • Detail

103-83-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N-Dimethylbenzylamine

1.2 Other means of identification

Product number -
Other names N,N-Dimethylbenzylam

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. CBI
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:103-83-3 SDS

103-83-3Related news

Reactions of N,N-Dimethylbenzylamine (cas 103-83-3) complex of palladium(II) with isocyanides08/20/2019

The reaction of N,N-dimethylbenzylamine complex of palladium(II) with isocyanides led to a cleavage of halide bridges to give (o-C6H4CH2NMe2)Pd(RNC)Cl 2. On heating of 2 in THF, an intramolecular insertion of coordinated isocyanide took place to give the dimeric iminoacyl complex 3. Treatment of...detailed

Thermal decomposition pattern of N,N-Dimethylbenzylamine (cas 103-83-3) complexes with silver (I), gold(III), zinc(II), cadmium(II) and mercury(II)08/19/2019

N,N-dimethylbenzylamine complexes with Ag(I), Au(III), Zn(II), Cd(II) and Hg(II) are reported. Characterization of the complexes is made on the basis of spectroscopic techniques and analytical data. Thermal decomposition patterns of the complexes are determined by thermogravimetric (TG) and diff...detailed

Reactions of palladium complex of N,N-Dimethylbenzylamine (cas 103-83-3) with aromatic phosphines bearing the methoxy groups at the 2,6-positions08/18/2019

Reactions of [(C6H4CH2NMe2-C2,N)PdCl]2 (1) with (2,6-dimethoxyphenyl)diphenylphosphine (MDMPP), bis(2,6-dimethoxyphenyl)phenylphosphine (BDMPP), and tris(2,6-dimethoxyphenyl)phosphine (TDMPP) gave the corresponding complexes [(C6H4CH2NMe2-C2,N)PdCl(L)] (2a: L=MDMPP; 2b: L=BDMMP; 2c: L=TDMPP). Re...detailed

Synthesis and characterization of SAPO-5 molecular sieve using N,N-Dimethylbenzylamine (cas 103-83-3) as template08/16/2019

The synthesis of SAPO-5 molecular sieves with high silicon contents has been attempted using N,N-dimethylbenzylamine as templating agent. SAPO-5 samples having silicon contents up to 35%, relative to total Si+Al+P, have been achieved. An increase in concentration of the templating agent in the s...detailed

Dramatic enhancement of the stability of rare-earth metal complexes with α-methyl substituted N,N-Dimethylbenzylamine (cas 103-83-3) ligands08/15/2019

Stepwise substitution of benzylic CH2 protons in ortho-metallated N,N-dimethylbenzylamine (dmba) ligands leads to chiral ortho-metallated N,N,α-trimethylbenzylamine (tmba) and cumyl-N,N-dimethylamine (cuda) ligands. These larger ligands with less or no acidic protons in benzylic position prove ...detailed

Benzimidazol-2-ylidene ligated palladacyclic complexes of N,N-Dimethylbenzylamine (cas 103-83-3) – Synthesis and application to C–C coupling reactions08/11/2019

Palladacyclic complexes derived from N,N-dimethylbenzylamine (dmba) and the benzimidazol-2-ylidene ligands: 1,3-di(cyclohexyl)benzimidazol-2-ylidene (BzImCy), 1,3-di(tert-butyl)benzimidazol-2-ylidene (BzImtBu) and 1,3-di(1-adamantyl)benzimidazol-2-ylidene (BzImAd) were prepared. The yield for (B...detailed

103-83-3Relevant articles and documents

-

Iversen

, p. 55 (1971)

-

Reductive Alkylations of Dimethylamine Using Titanium(IV) Isopropoxide and Sodium Borohydride: An Efficient, Safe, and Convenient Method for the Synthesis of N,N-Dimethylated Tertiary Amines

Bhattacharyya, Sukanta

, p. 4928 - 4929 (1995)

-

-

Van Koten et al.

, p. 2047,2049, 2052 (1977)

-

Metalated Mesoporous Poly(triphenylphosphine) with Azo Functionality: Efficient Catalysts for CO2 Conversion

Yang, Zhenzhen,Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Chen, Yu,Ma, Zhishuang,Ji, Guipeng,Gao, Xiang,Han, Buxing,Liu, Zhimin

, p. 1268 - 1273 (2016)

Mesoporous poly(triphenylphosphine) with azo functionality (poly(PPh3)-azo) is reported, which was synthesized via oxidative polymerization of P(m-NH2Ph)3 at ambient conditions. This kind of polymer could strongly coordinate with metal ions (e.g., Ru3+) and could reduce Ag+ in situ to metallic form. The resultant metalated poly(PPh3)-azo (e.g., poly(PPh3)-azo-Ag or -Ru) were discovered to be highly efficient catalysts for CO2 transformation. Poly(PPh3)-azo-Ag showed more than 400 times higher site-time-yield (STY) for the carboxylative cyclization of propargylic alcohols with CO2 at room temperature compared with the best heterogeneous catalyst reported. Poly(PPh3)-azo-Ru also exhibited good activity for the methylation of amines with CO2. It was demonstrated that the high performances of the catalysts originated from the cooperative effects between the polymer and the metal species. In addition, both catalysts showed good stability and easy recyclability, thus demonstrating promising potential for practical utilization for the conversion of CO2 into value-added chemicals.

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

Asad, Naeem,Deodato, Davide,Lan, Xin,Widegren, Magnus B.,Phillips, David Lee,Du, Lili,Dore, Timothy M.

, p. 12591 - 12600 (2017)

Representative tertiary amines were linked to the 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting group (PPG) to create photoactivatable forms suitable for use in studying cell physiology. The photoactivation of tamoxifen and 4-hydroxytamoxifen, which can be used to activate Cre recombinase and CRISPR-Cas9 gene editing, demonstrated that highly efficient release of bioactive molecules could be achieved through one- and two-photon excitation (1PE and 2PE). CyHQ-protected anilines underwent a photoaza-Claisen rearrangement instead of releasing amines. Time-resolved spectroscopic studies revealed that photorelease of the tertiary amines was extremely fast, occurring from a singlet excited state of CyHQ on the 70 ps time scale.

Slocum, D. W.,Marchal, R. L.,Jones, W. E.

, p. 227 - 237 (1974)

Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane

Mukherjee, Debabrata,Shirase, Satoru,Mashima, Kazushi,Okuda, Jun

, p. 13326 - 13329 (2016)

Triphenylborane (BPh3) was found to catalyze the reduction of tertiary amides with hydrosilanes to give amines under mild condition with high chemoselectivity in the presence of ketones, esters, and imines. N,N-Dimethylacrylamide was reduced to provide the α-silyl amide. Preliminary studies indicate that the hydrosilylation catalyzed by BPh3may be mechanistically different from that catalyzed by the more electrophilic B(C6F5)3.

Efficient and Selective N-Methylation of Nitroarenes under Mild Reaction Conditions

Pedrajas, Elena,Sorribes, Iván,Guillamón, Eva,Junge, Kathrin,Beller, Matthias,Llusar, Rosa

, p. 13205 - 13212 (2017)

Herein, we report a straightforward protocol for the preparation of N,N-dimethylated amines from readily available nitro starting materials using formic acid as a renewable C1 source and silanes as reducing agents. This tandem process is efficiently accomplished in the presence of a cubane-type Mo3PtS4 catalyst. For the preparation of the novel [Mo3Pt(PPh3)S4Cl3(dmen)3]+ (3+) (dmen: N,N′-dimethylethylenediamine) compound we have followed a [3+1] building block strategy starting from the trinuclear [Mo3S4Cl3(dmen)3]+ (1+) and Pt(PPh3)4 (2) complexes. The heterobimetallic 3+ cation preserves the main structural features of its 1+ cluster precursor. Interestingly, this catalytic protocol operates at room temperature with high chemoselectivity when the 3+ catalyst co-exists with its trinuclear 1+ precursor. N-heterocyclic arenes, double bonds, ketones, cyanides and ester functional groups are well retained after N-methylation of the corresponding functionalized nitroarenes. In addition, benzylic-type as well as aliphatic nitro compounds can also be methylated following this protocol.

Base-Catalyzed Hydrosilylation of Nitriles to Amines and Esters to Alcohols

Clarke, Joshua A.,Nikonov, Georgii I.,van der Est, Art

, p. 4434 - 4439 (2021)

Base-catalyzed hydrosilylation of nitriles to amines and esters to silylated alcohols is reported. This protocol tolerates electron-rich and electron-neutral olefins and works in the presence of basic functional groups (e. g. tertiary amines) but fails for acidic substrates, such as phenols and NH anilines. This catalytic system does not tolerate carbonyl groups, such as aldehydes, ketones, esters and carbamides, which are reduced to corresponding alcohols and amines. With the exact amount of silane, esters can be selectively reduced in the presence of nitriles, but the selectivity drops for the pairs ester/carboxamide and carboxamide/nitrile. Through competition experiments, the following preference in functional group reactivity was determined: ester > carboxamide > nitrile.

Lithium compound catalyzed deoxygenative hydroboration of primary, secondary and tertiary amides

Bisai, Milan Kumar,Gour, Kritika,Das, Tamal,Vanka, Kumar,Sen, Sakya S.

, p. 2354 - 2358 (2021)

A selective and efficient route for the deoxygenative reduction of primary to tertiary amides to corresponding amines has been achieved with pinacolborane (HBpin) using simple and readily accessible 2,6-di-tert-butyl phenolate lithium·THF (1a) as a catalyst. Both experimental and DFT studies provide mechanistic insight. This journal is

Self-encapsulation of homogeneous catalyst species into polymer gel leading to a facile and efficient separation system of amine products in the Ru-catalyzed reduction of carboxamides with polymethylhydrosiloxane (PMHS)

Motoyama, Yukihiro,Mitsui, Kaoru,Ishida, Toshiki,Nagashima, Hideo

, p. 13150 - 13151 (2005)

A practical procedure for production of amines is offered by the ruthenium-catalyzed reduction of carboxamides with polymethylhydrosiloxane, in which encapsulation of the catalyst species into the formed insoluble siloxane resins contributes to the separation of both metallic and siloxane residues from the product. Copyright

Transformation of Monoamine Oxidase-B Primary Amine Substrates into Time-Dependent Inhibitors. Tertiary Amine Homologues of Primary AMine Substrates

Ding, Charles Z.,Lu, Xingliang,Nishimura, Kuniko,Silverman, Richard B.

, p. 1711 - 1715 (1993)

A family of N-methylated and N,N-dimethylated alkyl and arylalkylamines was prepared and more than half of the analogues were shown to be time-dependent pseudo-first-order inhibitors of monoamine oxidase-B.Some of the time-dependent inactivators were reversible and others were irreversible with respect to prolonged dialysis following inactivation.Partition ratios ranged from zero to 11 000.These results are rationalized in terms of a combination of an inductive effect and a stereoelectronic effect as a result of hindered rotation of an active site covalent adduct.A molecualr mechanics calculation indicates that there is at least 10 kcal/mol of torsional energy to be overcome in order for the enzyme adduct to be released.These findings show that tertiary amine homologues of primary amine substrates of monoamino oxidase are time-dependent inhibitors, and this should be useful in the design of new inactivators of this enzyme.

Studies into reactions of N-methylmorpholine-N-oxide (NMMO) and its hydrates with cyanuric chloride

Rosenau, Thomas,Potthast, Antje,Kosma, Paul

, p. 9809 - 9815 (2002)

The course of the reaction between N-methylmorpholine-N-oxide (NMMO, 1a) and cyanuric chloride (2) is strictly dependent on the hydrate water content of the amine oxide. In solid phase, both substances undergo an explosion-like, extremely exothermic reaction. In solution, this process becomes controllable and leads to a quantitative degradation of NMMO into morpholine and formaldehyde, with 2 only acting as an inducing agent. The reaction can be conducted in a way that a clean deoxygenative demethylation is achieved. The monohydrate of NMMO (1b) is quantitatively converted into N-methylmorpholine and hypochlorous acid by the action of 2. This conversion can be used in synthesis either to deoxygenate tertiary amine N-oxide monohydrates, or to produce chlorohydrins in non-aqueous, organic media in superior yields. The semisesquihydrate of NMMO (1c) reacts with 2 under consumption of water until non-hydrated NMMO is present, which is then further converted into morpholine and HCHO, as in the case of 1a being directly employed as the starting material.

Iminopinacol coupling with lithium: Electron-transfer mediators

Mistryukov, Electron A.

, p. 230 - 231 (2002)

The addition of tert-butyl borate or ethyl formate to N-alkylbenzalimines directs the reaction pathway from the Birch reduction to the pinacol-type coupling with lithium in THF; an analogous reaction with a dimethylimmonium salt requires a trace titanium catalyst as the electron-transfer mediator.

Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis

Dong, Zhe,Wang, Jianchun,Dong, Guangbin

, p. 5887 - 5890 (2015)

Herein we report a highly meta-selective C-H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering a distinct strategy to control the site selectivity. The reaction was promoted by commercially available AsPh3 as the ligand and a unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed as the coupling partner. A wide range of functional groups, including some heteroarenes, are tolerated under the reaction conditions. In addition, the amine directing group can be easily installed and transformed to other common versatile functional groups. We expect this C-H functionalization mode to have broad implications for developing other meta-selective transformations beyond this work.

N,N-Diethylaniline·borane, an efficient reducing agent for reduction of representative functional groups

Salunkhe, Ashok M.,Burkhardt, Elizabeth R.

, p. 1519 - 1522 (1997)

N,N-Diethylaniline·borane (DEANB), a thermally stable, commercially available, amine·borane reagent, reduces a variety of functional groups, such as aldehydes, ketones, carboxylic acids, tertiary amides, and lactams in excellent yields. It also reduces Schiff bases to the corresponding amines in very good yields. Besides these reducing properties, it readily hydroborates 1-octene to provide the trialkylborane which in turn on alkaline peroxide oxidation furnished the 1-octanol in excellent yield and usual regioselectivity.

Mild and Efficient Flavin-Catalyzed H2O2 Oxidation of Tertiar Amines to Amine N-Oxides

Bergstad, Katarina,B?ckvall, Jan-E.

, p. 6650 - 6655 (1998)

A mild and highly effective H2O2 oxidation of tertiary amines has been developed by the use of flavin catalysis. Eight aliphatic amines were oxidized to their corresponding N-oxides in fast and selective reactions. For all substrates a considerable rate enhancement was observed compared to the noncatalyzed reactions. The product N-oxides were isolated in good yields using this mild oxidation system based on the environmentally attractive oxidant H2O2. As the catalyst, an N1N5- dialkylated flavin was used as an analogue of the biologically important flavin redox cofactor. The catalytic cycle proposed for the flavin catalysis accounts for the observation that, in addition to the hydrogen peroxide oxidant, molecular oxygen is required for the initiation of the process.

-

Saunders,Murray

, p. 1,8 (1960)

-

van Koten,Noltes

, p. 419,421,426 (1975)

A novel strategy for oligopeptide synthesis using a polymer-supported ammonium fluoride

Kurosu, Michio,Crick, Dean C.

, p. 5325 - 5328 (2006)

A novel method for the preparation of oligopeptides with a PS-ammonium fluoride in the solution phase is reported. The synthesis of lipid II pentapeptide is efficiently synthesized via a PS-ammonium fluoride without chromatographic purifications. The method reported here is very convenient to synthesize a relatively large amount of oligopeptides with abundantly available Fmoc-protected amino acids in a time efficient manner.

-

Kapicak,Gabbay

, p. 403,404, 405 (1975)

-

Cope et al.

, p. 4651,4655 (1960)

Gibson,Mann

, p. 175,180 (1942)

Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions

Liu, Jianguo,Ma, Longlong,Song, Yanpei,Zhang, Mingyue,Zhuang, Xiuzheng

supporting information, p. 4604 - 4617 (2021/06/30)

The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.

Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones

Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng

, p. 13824 - 13832 (2021/10/12)

A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.

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