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2-Dimethylaminopyridine

Base Information Edit
  • Chemical Name:2-Dimethylaminopyridine
  • CAS No.:5683-33-0
  • Molecular Formula:C7H10 N2
  • Molecular Weight:122.17
  • Hs Code.:29333999
  • European Community (EC) Number:227-147-5
  • NSC Number:93902
  • UNII:18Q95U3Z8H
  • DSSTox Substance ID:DTXSID9022231
  • Nikkaji Number:J51.314H
  • Wikidata:Q27252024
  • Mol file:5683-33-0.mol
2-Dimethylaminopyridine

Synonyms:2-Dimethylaminopyridine;5683-33-0;N,N-Dimethylpyridin-2-amine;2-(Dimethylamino)pyridine;dimethylaminopyridine;2-Pyridinamine, N,N-dimethyl-;2-Dimethylaminopyridin;Pyridine, 2-(dimethylamino)-;Dimethylamino-2 pyridine;N,N-Dimethyl-2-pyridinamine;Pyridinamine, N,N-dimethyl-;2-dimethylamino pyridine;EINECS 227-147-5;NSC 93902;(Dimethylamino)-2-pyridine;BRN 0110353;Dimethyl-pyridin-2-yl-amine;UNII-18Q95U3Z8H;2-Pyridinamide, N,N-dimethyl-;18Q95U3Z8H;PYRIDINE, 2-DIMETHYLAMINO-;NSC-93902;5-22-08-00287 (Beilstein Handbook Reference);Dimethylaminopyridin;dimethylamino pyridine;dimethlaminopyridine;Dimethyaminopyridine;dimethylaminopyndine;dimethlyaminopyridine;dimethylaminopiridine;dimethylaninopyridine;dimethyamino pyridine;MFCD00006261;dimethylamino-pyridine;dimethylamino~pyridine;(dimethylamino)pyridine;n,n-dimethylamino pyridine;SCHEMBL364;(n,n-dimethylamino)pyridine;2-Pyridinamine,N-dimethyl-;N-(2-Pyridyl)dimethylamine;(N,N- dimethylamino)pyridine;WLN: T6NJ BN1&1;DTXSID9022231;N,N-Dimethyl-2-pyridinamine #;2-(N,N-dimethylamino)-pyridine;AMY9407;Methyl-pyridin-2-yl-methyl-amine;2-(Dimethylamino)pyridine, 97%;Methyl-pyridin-2-yl -methyl-amine;NSC93902;N,N-DIMETHYLPYRIDIN-2-YLAMINE;AKOS005206861;SB53029;2-Pyridinamide, N,N-dimethyl- (9CI);AS-59067;BP-10156;LS-131425;A8125;CS-0112703;D1680;FT-0608797;D89909;EN300-7040398;W-203143;Q27252024

Suppliers and Price of 2-Dimethylaminopyridine
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • N,N-Dimethylpyridin-2-amine
  • 250mg
  • $ 45.00
  • TCI Chemical
  • 2-Dimethylaminopyridine >98.0%(GC)(T)
  • 500g
  • $ 590.00
  • TCI Chemical
  • 2-Dimethylaminopyridine >98.0%(GC)(T)
  • 25g
  • $ 73.00
  • Sigma-Aldrich
  • 2-(Dimethylamino)pyridine 97%
  • 25g
  • $ 88.90
  • Frontier Specialty Chemicals
  • 2-Dimethylaminopyridine 98%
  • 5g
  • $ 32.00
  • Frontier Specialty Chemicals
  • 2-Dimethylaminopyridine 98%
  • 25g
  • $ 129.00
  • Crysdot
  • N,N-Dimethylpyridin-2-amine 97%
  • 100g
  • $ 133.00
  • Crysdot
  • N,N-Dimethylpyridin-2-amine 97%
  • 25g
  • $ 45.00
  • Biosynth Carbosynth
  • 2-Dimethylaminopyridine
  • 10 g
  • $ 80.00
  • Biosynth Carbosynth
  • 2-Dimethylaminopyridine
  • 5 g
  • $ 50.00
Total 55 raw suppliers
Chemical Property of 2-Dimethylaminopyridine Edit
Chemical Property:
  • Appearance/Colour:Clear colorless to pale yellow. 
  • Vapor Pressure:1.98E-12mmHg at 25°C 
  • Melting Point:182°C 
  • Refractive Index:n20/D 1.559(lit.) 
  • Boiling Point:191 ºC 
  • PKA:7.04±0.10(Predicted) 
  • Flash Point:74 ºC 
  • PSA:16.13000 
  • Density:0.984 
  • LogP:1.14760 
  • Storage Temp.:Store below +30°C. 
  • Water Solubility.:Soluble in water. 
  • XLogP3:1.6
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:1
  • Exact Mass:122.084398327
  • Heavy Atom Count:9
  • Complexity:81
Purity/Quality:

97% *data from raw suppliers

N,N-Dimethylpyridin-2-amine *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes:Xi,T 
  • Statements: 36/37/38-34-23/24/25 
  • Safety Statements: 23-26-36-45-36/37/39-27 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Canonical SMILES:CN(C)C1=CC=CC=N1
  • General Description 2-Dimethylaminopyridine (DMAP) is a versatile catalyst and reagent widely used in organic synthesis, including esterification, acylation, and cycloaddition reactions. It is particularly effective in facilitating coupling reactions, such as those involving dicyclohexylcarbodiimide (DCC), and serves as a key component in the synthesis of complex molecules like liquid crystals, brassinosteroids, and β-aminocyclohexanecarboxylates. Its role in enhancing reactivity and selectivity in stereoselective transformations, such as nitrile oxide cycloadditions, highlights its importance in producing bioactive compounds and functionalized intermediates. Additionally, DMAP is utilized in organometallic chemistry, acting as a ligand or base in the formation of titanium-carbene complexes. Its broad applicability underscores its utility as a catalyst in diverse synthetic pathways.
Technology Process of 2-Dimethylaminopyridine

There total 54 articles about 2-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:
Guidance literature:
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide; In water; at 25 ℃; for 24h; Inert atmosphere;
DOI:10.1002/adsc.201400785
Guidance literature:
With 30%Cu-5%Ni/Al2O3 ; at 320 ℃; Reagent/catalyst; Inert atmosphere;
Guidance literature:
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide; In water; at 85 ℃; for 24h; Inert atmosphere;
DOI:10.1002/adsc.201400785
Refernces Edit

Synthesis, characterization, crystal structure and liquid crystal studies of some symmetric naphthalene derivative molecules

10.1016/j.molstruc.2018.07.036

This research focused on the synthesis, characterization, crystal structure, and liquid crystal studies of symmetric naphthalene derivative molecules. The purpose was to investigate the mesomorphic properties of a series of symmetrical liquid crystals with a naphthalene core and long-chain flexible 4′-alkoxybenzoate moieties. The study aimed to understand the correlation between molecular structure and physical properties, particularly the effects of varying alkyl chain lengths on mesomorphic properties. The chemicals used in the synthesis included 2,6-dihydroxynaphthalene, 4-alkoxybenzoic acids, dicyclohexylcarbodiimide (DCC) as a coupling reagent, and dimethylaminopyridine (DMAP) as a catalyst. The synthesized compounds exhibited stable enantiotropic mesophases of Smectic A (SmA) and Nematic (N) phases, with the appearance of these phases being independent of the alkyl chain length. The molecular structure was determined using single crystal X-ray diffraction, revealing a dihedral angle between the naphthalene ring system and the benzoate moiety. The study concluded that the synthesized naphthalene derivatives are predominantly smectogenic and partly nematogenic, with the mesomorphic range of the smectic phase being shorter than that of the nematic phase.

Synthesis of brassinosteroids of varying acyl side chains and evaluation of their brassinolide-like activity

10.1271/bbb.68.1097

The research details a study on the synthesis and evaluation of brassinosteroids, plant hormones known for their role in cell elongation and division, which are crucial for plant growth and stress resistance. The purpose of the study was to synthesize various brassinosteroids with different acyl side chains and assess their brassinolide-like activity, using the rice lamina inclination assay with synergist indole-3-acetic acid (IAA). The researchers concluded that the introduction of a hydroxyl group in the α-position to the carbonyl group of the ester structure significantly enhanced the activity, with 2β,3β-dihydroxy-17β-[(2R,3S)-2hydroxy-3-methylpentanoyl]oxy-B-homo-7-oxa-5β-androstan-6-one showing the highest activity. The study also found that the R-form of the acyl moiety was more potent than the S-form and that modifying the terminal structure did not increase activity. Chemicals used in the synthesis process included various steroidal compounds like pregnenolone and stigmasterol, as well as a range of reagents such as dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), and protective groups like tert-butyldiphenylsilyl (TBDPS).

Selective nitrile oxide dipolar cycloaddition for the synthesis of highly functionalized β-aminocyclohexanecarboxylate stereoisomers

10.1016/j.tet.2012.09.085

This research aims to synthesize highly functionalized β-aminocyclohexanecarboxylate stereoisomers from a bicyclic β-lactam through selective nitrile oxide dipolar cycloaddition. The process involves successive regioselective iodolactonization, stereo- and regioselective nitrile oxide cycloaddition, lactone ring-opening, and isoxazoline ring-opening. Key chemicals used include N-Boc-protected amino acids, NaHCO?, KI, I? for iodolactonization, DBU for dehydroiodination, NaOEt for lactone ring-opening, and acetonitrile N-oxide generated from nitroethane, di-tert-butoxycarbonylanhydride (Boc?O), and dimethylaminopyridine (DMAP) for cycloaddition. The study concludes that the rigid ring framework in unsaturated bicyclic amino lactones significantly enhances the reactivity of the C=C double bond compared to hydroxylated cyclohexene amino esters, leading to successful regio- and stereoselective cycloaddition. The synthesized compounds, with multiple stereocenters, are promising β-amino acid analogues of bioactive compounds like Tamiflu and Zanamivir.

A titanacyclobutane precursor to alkyl-substituted titanium-carbene complexes

10.1021/om00135a016

The research focuses on the synthesis and characterization of organometallic compounds, specifically metallacycles and titanium-carbene complexes. The purpose of the study was to prepare a titanacyclobutane precursor, which was then reacted with benzophenone to yield an organic product, and further reacted with phosphines to obtain phosphine adducts of an α-substituted titanium-carbene complex. The researchers also succeeded in creating a heterobimetallic alkylidene complex by reacting the metallacycle with dimethylaluminum chloride. The conclusions drawn from the study indicate that the observed reactivity of the metallacycle is consistent with productive cleavage of the metal-containing ring, leading to the formation of titanium-carbene complexes. The chemicals used in the process include 3,3-dimethylcyclopropene, Tebbe reagent, (dimethylamino)pyridine (DMAP), benzophenone, phosphines (PMeR2, where R = Me, Ph), and dimethylaluminum chloride, among others. The study provides insights into the reactivity of metallacycles and their potential as precursors to titanium-carbene compounds.

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