4-Dimethylaminopyridine

Base Information

• Chemical Name: 4-Dimethylaminopyridine
• CAS No.: 1122-58-3
• Deprecated CAS: 2011746-50-0
• Molecular Formula: C7H10N2
• Molecular Weight: 122.17
• Hs Code.: 29333999
• European Community (EC) Number: 214-353-5
• UNII: PFP1R6P0S8
• DSSTox Substance ID: DTXSID0044369
• Nikkaji Number: J1.582.952D,J31.394G
• Wikipedia: 4-dimethylaminopyridine
• Wikidata: Q229897
• ChEMBL ID: CHEMBL3561645
• Mol file: 1122-58-3.mol

Synonyms:Pyridine, 4-(dimethylamino)-;N,N-Dimethylpyridin-4-amine;4-Pyridinamine, N,N-dimethyl-;N,N-dimethyl-1H-pyridin-4-amine;4-(Dimethylamino)pyridine;p-Dimethylaminopyridine;4-Dimethylamino-pyridine(DMAP);4-Dimethylaminopyridine(DMAP);gamma-(Dimethylamino)pyridine;4-Pyridinamine,N,N-dimethyl-;DMAP (catalyst);4-Dimethylamino pyridine;4-(Dimethylamino) Pyridine;DMAP 4-Dimethylaminopyridine;4-Dimethylaminopy ridine;4-Dimethyl aminopyridine;4-Dimethylaminopyridine DMAP;4-Di(methylamino)pyridine;4-Dimethylamino-pyridine;DMAP (4-Dimethylaminopyridine);4-Dimethylaminopyridine (dmap);4-DMAP;4-Dimethyl amino pyridine;N4,N4-Dimethylpyridin-4-amine;4-（N,N-Dimethylamino)pyridine;

Chemical Property of 4-Dimethylaminopyridine

Chemical Property:

• Appearance/Colour: white to yellow crystalline powder
• Vapor Pressure: 0.431mmHg at 25°C
• Melting Point: 83-86 °C(lit.)
• Refractive Index: n20/D 1.431
• Boiling Point: 194.9 °C at 760 mmHg
• PKA: pKa (20°): 9.7
• Flash Point: 71.7 °C
• PSA: 16.13000
• Density: 1.012 g/cm³
• LogP: 1.14760
• Storage Temp.: Store in dark!
• Solubility.: methanol: 50 mg/mL, clear
• Water Solubility.: 76 g/L (25 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.084398327
• Heavy Atom Count: 9
• Complexity: 75

Purity/Quality:

98% ^*data from raw suppliers

4-Dimethylaminopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,C,T+
• Hazard Codes: T,C,T+,Xn,F
• Statements: 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25-67-66-21/22-11-36/37-22-19
• Safety Statements: 36/37/39-45-28A-26-28-36/37-53-27-22-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CN(C)C1=CC=NC=C1
• Chemical Properties: 4-Dimethylaminopyridine (4DMAP) is a derivative of pyridine. It is a colorless solid and serves as a useful nucleophilic catalyst for various reactions, including esterifications with anhydrides and hydrosilylations.
• Redox Properties: Modifications to the molecular skeleton of neutral bis-2-(4-dimethylamino)pyridinylidene electron donors, derived from 4DMAP, have been explored.; Variations in parameters such as the length of the polymethylene chain linking two pyridine-derived rings and the nature of nitrogen substituents led to alterations in redox profiles.
• Pharmaceutical Applications: Cocrystals/salt formations are studied for modulating the solubility, stability, and hygroscopicity of pharmaceutical ingredients. 4DMAP, with its ability to accept H-transfer, forms salts with organic acids, leading to complex non-covalent bonds.; The interaction between organic acids and 4DMAP involves dimer, catemer, and bridged motifs in the crystalline state, contributing to supramolecular crystal engineering.
• Supramolecular Crystal Engineering: Organic acids with suitable donor and acceptor properties play a crucial role in multi-component assembly, forming a dimer, caterer, and bridged synthons in the solid state. The interaction between organic acids and 4DMAP, with its subsidiary N(CH3)2, results in complex non-covalent bonds, facilitating supramolecular crystal engineering.

Technology Process of 4-Dimethylaminopyridine

There total 115 articles about 4-Dimethylaminopyridine 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: 99.4%

pyridine-4-carbonitrile (100-48-1) + dimethyl amine (124-40-3) → dmap (1122-58-3)

Guidance literature:

pyridine-4-carbonitrile; With hydrogenchloride; acrylic acid; at 90 ℃; for 1.5h; Inert atmosphere;

dimethyl amine; at 70 ℃; for 2.5h; Inert atmosphere;

With sodium hydroxide; at 70 - 90 ℃; for 3.5h; Temperature; Reagent/catalyst; Inert atmosphere;

Reference yield: 97.6%

4-aminopyridine (504-24-5) + methanol (67-56-1) → dmap (1122-58-3)

Guidance literature:

With 20%Cu-5%Co/Al₂O₃ ; at 320 ℃; Inert atmosphere;

Reference yield: 95.0%

4-(dimethylamino)pyridine N-oxide (1005-31-8) → dmap (1122-58-3)

Guidance literature:

With bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt; potassium iodide; In ethanol; at 20 ℃; for 1h;

DOI:10.1007/s13738-018-1381-4

upstream raw materials:

4-aminopyridine

methanol

4-phenoxypyridine

N,N-dimethylammonium chloride

Downstream raw materials:

4-(dimethylamino)pyridinium 5-(3,4-dichlorophenyl)-6,7-bis(hydroxymethyl)-2-<(carboxylatoethyl)carbonyl>-2,3-dihydro-1H-pyrrolizine bis(2-propylcarbamate)

4-hydroxy-benzaldehyde

meta-hydroxybenzaldehyde

meta-nitrophenol

Refernces

• 1、 Su,Watson. "-". . p. 1854. Retrieved 1974.
• 2、 Petersen, Trine P.,Larsen, Anders Foller,Ritzen, Andreas,Ulven, Trond. "Continuous flow nucleophilic aromatic substitution with dimethylamine generated in situ by decomposition of DMF". . p. 4190 - 4195. Retrieved 2013.
• 3、 Filimonov, V. D.,Krasnokutskaya, E. A.,Potapova, M. I.,Sanzhiev, A. N.. "A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid". . p. 1023 - 1028. Retrieved 2020.
• 4、 Anderson,Seeger. "-". . p. 340. Retrieved 1949.
• 5、 Alzoubi, Basam M.,Hamza, Mohamed S. A.,Duecker-Benfer, Carlos,Van Eldik, Rudi. "Mechanistic insight gained into the ligand substitution reactions of bis(o-benzosemiquinonediiminato)(triphenylphosphane)cobalt(III) - Kinetic, solvent, and volume profile studies". . p. 2972 - 2978. Retrieved 2003.
• 6、 Wompe et al.. "-". . p. 361. Retrieved 1958.
• 7、 Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami. "Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies". . p. 1237 - 1242. Retrieved 2021/06/01.
• 8、 García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.. "A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics". supporting information. . Retrieved 2022/01/04.