N-Methylbenzylamine

Base Information

• Chemical Name: N-Methylbenzylamine
• CAS No.: 103-67-3
• Deprecated CAS: 854881-74-6
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 29214980
• European Community (EC) Number: 203-133-4
• NSC Number: 8059
• UNII: 7KN7F4X49E
• DSSTox Substance ID: DTXSID9048439
• Nikkaji Number: J28.348G
• Wikidata: Q23978278
• Metabolomics Workbench ID: 123338
• ChEMBL ID: CHEMBL1338
• Mol file: 103-67-3.mol

Synonyms:N-benzyl methyl ammonium;N-benzyl-N-methylamine;N-methylbenzylamine;N-methylbenzylamine acetate;N-methylbenzylamine hydride;N-methylbenzylamine hydrochloride;N-methylbenzylamine tosylate

Chemical Property of N-Methylbenzylamine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.893mmHg at 25°C
• Melting Point: -24 °C
• Refractive Index: 1.5230
• Boiling Point: 180.5 °C at 760 mmHg
• PKA: 9.75±0.10(Predicted)
• Flash Point: 77.8 °C
• PSA: 12.03000
• Density: 0.939 g/mL at 25 °C(lit.)
• LogP: 1.79690
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 65g/l
• Water Solubility.: 65 g/L (20 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 65

Purity/Quality:

99% ^*data from raw suppliers

N-Methylbenzylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-42/43-22
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CNCC1=CC=CC=C1
• Recent ClinicalTrials: Phase 3, Double-blind, Randomized, Placebo-controlled Trial to Evaluate the Efficacy and Safety of AR1001 in Participants With Early Alzheimer's Disease (Polaris-AD)
• Uses: N-Benzylmethylamine is used in the production of dyes. It can be also used as catalytic agent, Petrochemical additive.

Technology Process of N-Methylbenzylamine

There total 259 articles about N-Methylbenzylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

N-methylbenzamide (88070-48-8) → N-Benzylidenemethylamine (622-29-7) + benzyl-methyl-amine (103-67-3)

Guidance literature:

With triethyl borane; phenylsilane; potassium tert-butylate; In pentane; at 50 ℃; for 48h; Reagent/catalyst; chemoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/acs.joc.9b00277

Reference yield: 9.0%

N,N-dimethylbenzylamine N-oxide (5400-82-8) → piperazine-2,3 diphenyl N,N-dimethyl trans (81577-03-9) + benzaldehyde (100-52-7) + piperazine-2,3 diphenyl N,N-dimethyl cis (81577-01-7) + benzyl-methyl-amine (103-67-3)

Guidance literature:

With DAL; at 0 ℃; Yield given. Yields of byproduct given;

Reference yield: 4.0%

2,4,6,8,10,12-hexabenzyl-2,4,5,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane (124782-15-6) → 1-benzylimidazole (4238-71-5) + 1,3-dibenzyl-1,3-diazolidine (42164-42-1) + N,N'-dibenzylpiperazine (1034-11-3) + benzyl-methyl-amine (103-67-3) + 3-benzyl-1,3,5-triazacycloheptane + benzylamine (100-46-9)

Guidance literature:

With hydrogen; In ethyl acetate; at 100 ℃; for 8h; under 7500.6 Torr; Product distribution; degradation investigated by MS;

DOI:10.1016/0040-4020(95)00155-2

upstream raw materials:

chloromethyltriethoxysilane

benzylamine

N,N-dimethyl-formamide

carbonic acid dimethyl ester

Downstream raw materials:

2-(N-benzyl-N-methyl)amino-1-ethanol

(1-ethyl-[3]piperidyl)-benzyl-methyl-amine

benzyl-methyl-(2-[4]pyridyl-ethyl)-amine

2-[(benzyl-methyl-amino)-methyl]-pyridin-3-ol

Refernces

• 1、 Lebleu, Thomas,Kotsuki, Hiyoshizo,Maddaluno, Jacques,Legros, Julien. "Formylation of amines through catalyst- and solvent-free transamidation reaction". . p. 362 - 364. Retrieved 2014.
• 2、 Anderson,Veysoglu. "-". . p. 665. Retrieved 1974.
• 3、 Euerby, Melvin R.,Waigh, Roger D.. "Methylthio Activating Groups in the Synthesis of Isoquinolines". . p. 127 - 128. Retrieved 1984.
• 4、 Brown, Herbert C.,Narasimhan, S.,Choi, Yong Moon. "Improved Procedure for Borane-Dimethyl Sulfide Reduction of Tertiary and Secondary Amides in the Presence of Boron Trifluoride Etherate". . p. 996 - 997. Retrieved 1981.
• 5、 Obora, Yasushi,Ohta, Tetsuo,Stern, Charlotte L.,Marks, Tobin J.. "Organolanthanide-catalyzed imine hydrogenation. Scope, selectivity, mechanistic observations, and unusual byproducts". . p. 3745 - 3755. Retrieved 1997.
• 6、 Cho, Bong Rae,Namgoong, Sung Keon,Bartsch, Richard A.. "Reactions of N-Chlorobenzylmethylamines with Secondary Amines in Acetonitrile. Effect of Base Strength upon the Imine-Forming Transition State". . p. 1320 - 1324. Retrieved 1986.
• 7、 Vellem?e, Eerold,Lebedev, Oleg,M?eorg, Uno. "A mild method for cleavage of N-Tos protected amines using mischmetal and TiCl4". . p. 1373 - 1375. Retrieved 2008.
• 8、 Peterson, Lisa A.. "N-Nitrosobenzylmethylamine is activated to a DNA benzylating agent in rats". . p. 19 - 26. Retrieved 1997.
• 9、 Harding, John R.,Jones, John R.,Lu, Shui-Yu,Wood, Robin. "Development of a microwave-enhanced isotopic labelling procedure based on the Eschweiler-Clarke methylation reaction". . p. 9487 - 9488. Retrieved 2002.
• 10、 Lorand, John P.,Anderson, James L.,Shafer, Brian P.,Verral, Daniel L.. "On the Thermal Deoxygenation of 1-(Dimethylamino)adamantane N-Oxide". . p. 1560 - 1563. Retrieved 1993.