N,N-Dimethylbenzylamine

Base Information

• Chemical Name: N,N-Dimethylbenzylamine
• CAS No.: 103-83-3
• Deprecated CAS: 59125-51-8,1338002-71-3,1236382-77-6,1338002-71-3
• Molecular Formula: C9H13N
• Molecular Weight: 135.209
• Hs Code.: 29214980
• European Community (EC) Number: 203-149-1
• ICSC Number: 1340
• NSC Number: 5342
• UN Number: 2619
• UNII: TYP7AXQ1YJ
• DSSTox Substance ID: DTXSID8021854
• Nikkaji Number: J36.099F
• Wikipedia: Dimethylbenzylamine
• Wikidata: Q424966
• Metabolomics Workbench ID: 135498
• ChEMBL ID: CHEMBL45591
• Mol file: 103-83-3.mol

Synonyms:BDMA;benzyldimethylamine;N,N-dimethylbenzylamine;N-benzyl-N,N-dimethylamine;N-benzyl-N,N-dimethylamine hydrobromide;N-benzyl-N,N-dimethylamine hydrochloride;N-benzyl-N,N-dimethylamine nitrate

Chemical Property of N,N-Dimethylbenzylamine

Chemical Property:

• Appearance/Colour: Colourless to light yellow liquid
• Vapor Pressure: 0.871mmHg at 25°C
• Melting Point: -75 °C
• Refractive Index: n20/D 1.501(lit.)
• Boiling Point: 181 °C at 760 mmHg
• PKA: pK1:9.02(+1) (25°C)
• Flash Point: 130 °F
• PSA: 3.24000
• Density: 0.9 g/mL at 25 °C(lit.)
• LogP: 1.74820
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: water: soluble
• Water Solubility.: 8 g/L (20 ºC)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 135.104799419
• Heavy Atom Count: 10
• Complexity: 82.7
• Transport DOT Label: Corrosive Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

N,?N-?Dimethylbenzylamine(Benzyldimethylamine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-20/21/22-34-52/53
• Safety Statements: 26-36-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CN(C)CC1=CC=CC=C1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• Uses: Intermediate, especially for quaternary ammonium compounds; dehydrohalogenating catalyst; corrosion inhibitor; acid neutralizer; potting compounds; adhesives; cellulose modifier. 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. 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.

Technology Process of N,N-Dimethylbenzylamine

There total 216 articles about N,N-Dimethylbenzylamine 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: 25.0%

N-nitrodimethylamine (4164-28-7) → N,N'-dimethylbenzylamine (103-83-3) + N-methylmethanimine (1761-67-7) + dimethyl amine (124-40-3) + dimethylnitrosamine (62-75-9)

Guidance literature:

With nitrogen(II) oxide; toluene; Kinetics; Mechanism; Product distribution; Irradiation; various temperatures, scavengers, with or without NO;

DOI:10.1021/j100340a020

Reference yield: 10.0%

N,N-dimethylbenzylamine N-oxide (5400-82-8) → N,N'-dimethylbenzylamine (103-83-3) + benzaldehyde (100-52-7)

Guidance literature:

With AFA; In dichloromethane; at 0 - 21 ℃;

DOI:10.1246/cl.1985.1517

Reference yield: 6.0%

N,N-dimethylthiobenzamide (15482-60-7) → N,N'-dimethylbenzylamine (103-83-3) + dibenzyl disulphide (150-60-7) + phenylmethanethiol (100-53-8)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; for 26h; Heating;

upstream raw materials:

formaldehyd

formic acid

3-(benzylamino)propionitrile

1-benzyl-3,5,7-triaza-1-azoniatricyclo<3,3,1,1^3,7>decane chloride

Downstream raw materials:

4-methylbenzoic acid benzyl ester

benzyl-dimethyl-phenoxycarbonylmethyl-ammonium; chloride

N,N'-dibenzyl-tetra-N-methyl-N,N'-pentanediyl-di-ammonium; dibromide

N,N'-dibenzyl-N,N,N',N'-tetramethyl-N,N'-hexanediyl-di-ammonium; dibromide

Refernces

• 1、 Yang, Zhenzhen,Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Ji, Guipeng,Ma, Zhishuang,Gao, Xiang,Liu, Zhimin. "B(C6F5)3-catalyzed methylation of amines using CO2 as a C1 building block". . p. 4189 - 4193. Retrieved 2015.
• 2、 Monson,Priest. "". . p. 1018. Retrieved 1971.
• 3、 Blom, Burgert,Tan, Gengwen,Enthaler, Stephan,Inoue, Shigeyoshi,Epping, Jan Dirk,Driess, Matthias. "Bis- n -heterocyclic carbene (nhc) stabilized η6-arene iron(0) complexes: Synthesis, structure, reactivity, and catalytic activity". . p. 18108 - 18120. Retrieved 2013.
• 4、 Ashby,Garnett. "". . p. 549,552. Retrieved 1963.
• 5、 Chauvin. "Reaction of alkyl sulfoxides and phenylphosphinic acid with amines. Alternative reagents for secondary amines N-alkylation". . p. 1425 - 1428. Retrieved 1991.
• 6、 Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me. "Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines". . p. 2005 - 2009. Retrieved 2017.
• 7、 Smith,Marcucci,Tingue. "Base-promoted elimination reactions of acetaldehyde N-alkyl-N,N-dimethylhydrazonium salts. A convenient synthesis of N,N-dimethylalkylamines". . p. 381 - 389. Retrieved 1992.
• 8、 Proni et al.. "-". . p. 47. Retrieved 1977.
• 9、 Yang, Zhenzhen,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Ma, Zhishuang,Ji, Guipeng,Han, Buxing,Liu, Zhimin. "Azo-functionalized microporous organic polymers: Synthesis and applications in CO2 capture and conversion". . p. 11576 - 11579. Retrieved 2015.
• 10、 Erdik, Ender,Ates, Selma. "Synthesis of N,N-dimethylamines via Barbier-Grignard-type electrophilic amination". . p. 2813 - 2818. Retrieved 2006.