2-Dimethylaminopyridine

Base Information

• 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

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

Chemical Property of 2-Dimethylaminopyridine

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:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• 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
• Uses: 2-(Dimethylamino)pyridine in toluene at room temperature in the presence of 1.1 equivalent of methyl trifluoromethanesulfonate forms (2-pyridyl)-trimethylammonium trifluoromethanesulfonate salt. It is used as a model substrate in the preparation of chelate carbene via cyclometalation, H2 loss and reversible α-elimination.

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:

Reference yield: 95.0%

2-iodopyridine (5029-67-4) + dimethyl amine (124-40-3) → 2-(Dimethylamino)pyridine (5683-33-0)

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

Reference yield: 93.5%

2-aminopyridine (504-29-0) + methanol (67-56-1) → 2-(N-methylamino)pyridine (4597-87-9) + 2-(Dimethylamino)pyridine (5683-33-0)

Guidance literature:

With 30%Cu-5%Ni/Al₂O₃ ; at 320 ℃; Reagent/catalyst; Inert atmosphere;

Reference yield: 92.0%

2-bromo-pyridine (109-04-6) + dimethyl amine (124-40-3) → 2-(Dimethylamino)pyridine (5683-33-0)

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

upstream raw materials:

pyridine

methyl iodide

2-aminopyridine

methanol

Downstream raw materials:

(6-(dimethylamino)pyridin-3-yl)methanol

trimethylpyridin-2-ylammonium iodide

5-bromo-2-dimethylaminopyridine

3,5-dibromo-N,N-dimethylpyridin-2-amine

Refernces

• 1、 Isshiki, Ryota,Kurosawa, Miki B.,Muto, Kei,Yamaguchi, Junichiro. "Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction". . p. 10333 - 10340. Retrieved 2021/07/21.
• 2、 Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao. "Nickel-Catalyzed Amination of Aryl Chlorides with Amides". supporting information. p. 687 - 691. Retrieved 2021/01/09.