4-Dimethylaminopyridine

• CAS: 1122-58-3
• Catalog Number: ACM1122583
• Category: Main Products
• Molecular Weight: 122.17
• Molecular Formula: C7H10N2
• Description: 4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This colourless solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent.Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. Chiral DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxiliary type amides.
• Synonyms: 4-Dimethylaminopyrid;AURORA KA-6495;N-(4-Pyridyl)dimethylamine;4-Pyridinamine, N,N-dimethyl-;4-Dimethylaminepyridine
• IUPAC Name: 4-Dimethylaminopyridine
• Boiling Point: 211°C
• Melting Point: 108-113ºC
• Flash Point: 110ºC
• Density: 1.012 g/cm³
• Appearance: White to yellow crystalline powder
• EC Number: 214-353-5
• Exact Mass: 122.08400
• Hazard Codes: T
• Hazard Statements: T,C,T+,Xn,F
• HS Code: 2933399090
• LogP: 1.14760
• MDL Number: MFCD00006418
• Packing Group: II
• PSA: 16.13
• Refractive Index: n20/D 1.431
• RIDADR: UN 1760/2811
• Safety Description: 36/37/39-45-28A-26-28-36/37-53-27-22-16
• Stability: Stable. Incompatible with acids, oxidizing agents.
• Storage Conditions: Store in dark
• Supplemental Hazard Statements: H314-H318-H402-H301-H310-H315-H319-H335-H302-H311-H351-H225-H302+H312-H336
• Symbol: GHS08,GHS02,GHS06,GHS07,GHS05
• Vapor Pressure: 0.431mmHg at 25°C
• WGK Germany: 3

Case Study

4-Dimethylaminopyridine Catalyzed Multi-Component One-Pot Method for the Synthesis of Spirooxindole Derivatives

Jun Feng, et al. Tetrahedron, 2014, 70(2), 484-489.

A multicomponent one-pot reaction for the synthesis of spirooxindole derivatives in EtOH using 4-dimethylaminopyridine (4-DMAP) as catalyst has been developed. These reactions include one-pot three-component reactions and one-pot four-component reactions.
General synthesis procedures
· The three-component one-pot synthesis of 6'-amino-3'-methyl-2-oxo-2'H-spiro[indoline3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile: The combination of 3-methyl-5-pyrazolone 1a (1 mmol), isatin 3 (1 mmol), malononitrile 4a (1 mmol), and 4-DMAP (0.1 mmol) in EtOH (20 mL) was heated and stirred at 60 °C for 60 min. Once TLC confirmed the reaction was complete, the mixture was allowed to cool to room temperature. The resulting product was filtered out, washed with water and then cooled EtOH (50%), leading to the pure product 5a with a high yield.
· The four-component one-pot reaction synthesis of ethyl 6'-amino-3'-methyl-2-oxo-2'H-spiro [indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate: A mixture of ethyl acetoacetate 1 (1 mmol), hydrazine 2 (1 mmol), isatin 3 (1 mmol), ethyl cyanoacetate 4b (1 mmol), and 4- DMAP (0.1 mmol) in EtOH (20 mL) was stirred at 60 °C for 60 min. After confirming the completion of the reaction by TLC, the reaction mixture was cooled, filtered and washed to obtain pure product 6a in good yield.

Catalytic Depolymerization of Polylactide by 4-Dimethylaminopyridine

Alberti, Christoph, et al. ChemistrySelect, 2019, 4(23), 6845-6848.

The selective degradation of polylactide (PLA) preparations to methyl lactate can be achieved by applying a combination of methanol and catalytic amounts of 4-dimethylaminopyridine (DMAP). This work proposes an efficient chemical recycling strategy for end-of-life plastics/polymers.
General procedure for the depolymerization of polylactide via DMAP
· A mixture containing 97.2 mg of polylactide (1a) (1.35 mmol based on the repeating unit), methanol (0.125-2.00 g, 2.89-31.2 mmol, 2.9-46.3 equiv. based on the repeating unit of 1a), and catalytic amounts of 4 dimethylaminopyridine (0-5 mol%, 0-0.0675 mmol based on the repeating unit of 1a) was placed in a vial with a stir bar.
· If less than 23.1 equiv. of methanol was used, THF was added as a solvent (1 g). The vial was sealed and placed in a Microwave Synthesis Reactor Monowave 400. The reaction was conducted for 5-60 minutes (hold time) at 100-180 °C and with a stirring speed of 600 rpm. The reaction temperature was achieved within 1-2 minutes (heated rapidly).
· Subsequently, the vial was cooled to room temperature. A portion of the clear solution was moved to a NMR tube and dissolved in CDCl. The sample was analyzed by 'H NMR to determine the yield of methyl lactate (2).

Custom Q&A

What is the molecular formula of 4-Dimethylaminopyridine?

The molecular formula of 4-Dimethylaminopyridine is C7H10N2.

What is the molecular weight of 4-Dimethylaminopyridine?

The molecular weight of 4-Dimethylaminopyridine is 122.17 g/mol.

What is the IUPAC name of 4-Dimethylaminopyridine?

The IUPAC name of 4-Dimethylaminopyridine is N,N-dimethylpyridin-4-amine.

What is the InChI of 4-Dimethylaminopyridine?

The InChI of 4-Dimethylaminopyridine is InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3.

What is the InChIKey of 4-Dimethylaminopyridine?

The InChIKey of 4-Dimethylaminopyridine is VHYFNPMBLIVWCW-UHFFFAOYSA-N.

What are the other identifiers of 4-Dimethylaminopyridine?

The other identifiers of 4-Dimethylaminopyridine include CAS number 1122-58-3, EC Number 214-353-5, UNII PFP1R6P0S8, DSSTox Substance ID DTXSID0044369, and ChEMBL ID CHEMBL3561645.

What is the physical description of 4-Dimethylaminopyridine?

The physical description of 4-Dimethylaminopyridine is Pel.

What is the XLogP3 value of 4-Dimethylaminopyridine?

The XLogP3 value of 4-Dimethylaminopyridine is 1.3.

How many hydrogen bond acceptor counts does 4-Dimethylaminopyridine have?

4-Dimethylaminopyridine has 2 hydrogen bond acceptor counts.

How many rotatable bond counts does 4-Dimethylaminopyridine have?

4-Dimethylaminopyridine has 1 rotatable bond count.

Synthetic Use

Downstream Synthesis Route 1

• 75-44-5
• 1122-58-3
• 1193-24-4

• 1193-21-1

Reference: [1] Patent: US5750694, 1998, A,

Downstream Synthesis Route 2

• 1122-58-3

• 50533-97-6

Reference: [1] New Journal of Chemistry, 2008, vol. 32, # 6, p. 1027 - 1037

Downstream Synthesis Route 3

• 1122-58-3

• 84539-35-5

Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069

Downstream Synthesis Route 4

• 590-92-1
• 1122-58-3

• 89389-94-6

Reference: [1]Journal of Organic Chemistry,1991,vol. 56,p. 6516 - 6521

Downstream Synthesis Route 5

• 1122-58-3
• 4232-27-3

• 28767-46-6
• 20350-26-9

Reference: [1]Chemistry Letters,1993,p. 517 - 520

* For details of the synthesis route, please refer to the original source to ensure accuracy.