5683-33-0

Basic information

• Product Name: 2-Dimethylaminopyridine
• Synonyms: (Dimethylamino)-2-pyridine;2-Dimethylaminopyridin;(2-Pyridinyl)dimethylamine;2-(N,N-dimethylamino)pyridine;2-(DIMETHYLAMINO)PYRIDINE FOR SYNTHESIS;2-dimethylamino-pyridin;2-Dimethylaminopyridine cobalt complex;2-Pyridinamine, N,N-dimethyl-
• CAS NO: 5683-33-0
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• EINECS: 227-147-5
• Product Categories: C7 and C8;Heterocyclic Building Blocks;Pyridines;Heterocyclic Compounds
• Mol File: 5683-33-0.mol
• Article Data: 39

Chemical Properties

• Melting Point: 182°C
• Boiling Point: 191 °C(lit.)
• Flash Point: 167 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.98E-12mmHg at 25°C
• Refractive Index: n20/D 1.559(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 7.04±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 110353
• CAS DataBase Reference: 2-Dimethylaminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Dimethylaminopyridine(5683-33-0)
• EPA Substance Registry System: 2-Dimethylaminopyridine(5683-33-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-34-23/24/25
• Safety Statements: 23-26-36-45-36/37/39-27
• RIDADR: 1993
• WGK Germany: 3
• RTECS: US9200000
• F: 10
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 5683-33-0(Hazardous Substances Data)

Usage

Description

2-Dimethylaminopyridine, also known as 2-(Dimethylamino)pyridine, is a clear, colorless to light yellow liquid with chemical properties that make it a versatile compound in various applications. It is characterized by its clear colorless to pale yellow appearance and is known for its use in chemical reactions and as a model substrate in the preparation of chelate carbene.

Uses

Used in Chemical Synthesis:
2-Dimethylaminopyridine is used as a catalyst in the chemical synthesis industry for its ability to facilitate reactions and improve the efficiency of the process. It is particularly useful in the formation of (2-pyridyl)-trimethylammonium trifluoromethanesulfonate salt when reacted with toluene at room temperature in the presence of methyl trifluoromethanesulfonate.
Used in Research and Development:
In the field of research and development, 2-Dimethylaminopyridine serves as a model substrate for the preparation of chelate carbene via cyclometalation, H2 loss, and reversible α-elimination. This application is crucial for understanding the underlying mechanisms and reactions involved in the formation of complex organic compounds.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Dimethylaminopyridine is also known for its applications in the pharmaceutical industry. It can be used as an intermediate in the synthesis of various drugs, particularly those targeting the central nervous system, due to its ability to modulate specific receptors and biological processes.

InChI:InChI=1/C18H18N2O2S2/c1-18(2)8-12-13(10-22-18)24-15-14(12)16(21)20(17(23)19-15)9-11-6-4-3-5-7-11/h3-7H,8-10H2,1-2H3,(H,19,23)

Upstream product

• 504-29-0 2-aminopyridine 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 40825-17-0 Natrium-Verbindung des [2]Pyridylamins 
• 74-88-4 methyl iodide 
• 109-09-1 2-chloropyridine 
• 100-00-5 4-chlorobenzonitrile 
• 626-64-2 pyridin-4-ol 
• 337913-25-4 phosphorus pentaoxide 
• 67-68-5 dimethyl sulfoxide 
• 5029-67-4 2-iodopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 372-48-5 2-fluoropyridine 
• 1579202-92-8 S-n-butyl 2-pyridinecarbothioate 

Downstream Products

• 26163-07-5 5-bromo-2-dimethylaminopyridine 
• 475682-46-3 [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate 
• 166964-10-9 N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 
• 121170-48-7 (R)-(+)-4-(1,1,1-trifluoro-2-octyloxycarbonyl)-4'-benzyloxybiphenyl 
• 144055-88-9 ethyl-4-amino-3-[3'-(N-tert-butyloxycarbonylamino)-1'-acetoxyiminopropyl]benzoate 
• 175082-11-8 tripropylene glycol-di-p-tosylate 
• 130737-48-3 2'-Hydroxy-3'-methyl-4'-trifluoromethanesulfonyloxy-acetophenone 
• 326599-01-3 Methyl (1R,3S,5R)-3-acetoxy-5-tosyloxy-cyclohexanecarboxylate 
• 82582-67-0 [Ir(hydrido)2(acetone)2(triphenylphosphine)2](BF4) 
• 334543-31-6 trans-[hydrido(acetone)bis(triphenylphosphine)(N,C-2-(dimethylamino)pyridine-1'-yl)iridium(III)] fluoroborate 
• 16219-98-0 N-methyl-N-(pyridin-2-yl)nitrous amide 
• 1036991-24-8 N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine 

Relevant articles and documents

Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.

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.

A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid

Abstract: Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic synthesis.