Production Method 1

10441-57-3

872-50-4

Reaction Conditions

1.1 Reagents: Trifluoroacetic anhydride Solvents: Dichloromethane

Reference

An alternative efficient method for transformation of thiocarbonyl to carbonyl group using trifluoroacetic anhydride

Masuda, Ryoichi; et al, Tetrahedron Letters, 1991, 32(9), 1195-8

Production Method 2

33693-57-1

872-50-4

Reaction Conditions

1.1 Catalysts: Indium Solvents: Water

Reference

Indium-mediated reductive dehalogenation of α-halo carbonyl compounds in water

Park, Leeyoung; et al, Perkin 1, 2000, (24), 4462-4463

Production Method 3

872-50-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene ;  24 h, rt

Reference

Asymmetric synthesis and evaluation of α-quaternary chiral lactam derivatives as novel anticancer agents

Lee, Hwanhyuk; et al, Archives of Pharmacal Research, 2014, 37(10), 1264-1270

Production Method 4

108-31-6

872-50-4

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Manganese ,  Sodium ,  Cobalt ,  Copper ,  Phosphoric acid Solvents: Water

Reference

Process for the preparation of N-substituted 2-pyrrolidones with additional product recovery from the distillation residues.

, European Patent Organization, , ,

Production Method 5

14874-70-5

514224-16-9

872-50-4

Reaction Conditions

1.1 Reagents: Silver acetate Solvents: Tetrahydrofuran ;  4 h, rt

Reference

Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: vinylic SN2-based strategy for conversion of tertiary thioamides to amides

Ochiai, Masahito; et al, Chemical Communications (Cambridge, 2002, (23), 2802-2803

Production Method 6

10441-57-3

872-50-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Vanadate(6-), nona-μ-oxotrioxo(pentadeca-μ-oxononaoxononamolybdate)[μ12-[phospha… Solvents: Acetonitrile ;  5 h, 1 atm, 90 °C

Reference

Phosphovanadomolybdic acid catalyzed desulfurization-oxygenation of secondary and tertiary thioamides into amides using molecular oxygen as the terminal oxidant

Xu, Ning; et al, New Journal of Chemistry, 2016, 40(6), 4865-4869

Production Method 7

10441-57-3

872-50-4

Reaction Conditions

1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane

Reference

Facile conversion of thioamides into amides

Kochhar, Kanwarpal S.; et al, Tetrahedron Letters, 1983, 24(13), 1323-6

Production Method 8

1121-07-9

872-50-4

Reaction Conditions

1.1 Catalysts: Ruthenium Solvents: Water

Reference

Regenerable N-alkylamide hydroperoxide for catalytic substrate oxidation

Patton, Douglas E.; et al, Journal of the Chemical Society, 1993, (14), 1611-15

Production Method 9

1121-07-9

872-50-4

Reaction Conditions

1.1 Reagents: Vitride Solvents: Toluene ,  Water

Reference

Properties of sodium bis(2-methoxyethoxy)aluminum hydride IV. Reduction of oximes, amides, lactams, imides, and nitriles

Cerny, Miloslav; et al, Collection of Czechoslovak Chemical Communications, 1969, 34(3), 1033-41

Production Method 10

120-94-5

872-50-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Alumina ,  Gold Solvents: Water ;  24 h, 80 °C

Reference

Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides

Jin, Xiongjie; et al, Angewandte Chemie, 2016, 55(25), 7212-7217

Production Method 11

120-94-5

872-50-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Gold ,  Silica Solvents: 1,4-Dioxane ,  Water ;  1 min, rt; rt → 100 °C; 3.5 h, 100 °C

Reference

Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by Ceria-Supported Nanogold

Dairo, Taiwo O.; et al, Catalysis Letters, 2016, 146(11), 2278-2291

Production Method 12

512-56-1

872-50-4

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  15 min, 0 °C
1.2 24 h, 120 °C
1.3 Reagents: Ammonium chloride

Reference

Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates

Banerjee, Amit; et al, Synthesis, 2023, 55(2), 315-332

Production Method 13

872-50-4

Reaction Conditions

1.1 Reagents: Poly(methylhydrosiloxane) ,  Methylsilanediol homopolymer Catalysts: Copper ,  Formaldehyde, polymer with 1,3,5-benzenetriol and 1,3,5-triazine-2,4,6-triamine Solvents: Acetonitrile ;  12 h, 80 °C

Reference

Triazinetriamine-derived porous organic polymer-supported copper nanoparticles (Cu-NPs@TzTa-POP): an efficient catalyst for the synthesis of N-methylated products via CO2 fixation and primary carbamates from alcohols and urea

Haque, Najirul; et al, New Journal of Chemistry, 2020, 44(36), 15446-15458

Production Method 14

108-31-6

872-50-4

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Chromia ,  Copper
1.2 Reagents: Water

Reference

Preparation of pyrrolidone and N-alkylpyrrolidones from copper-metal oxide-catalyzed cyclization of 1,4-dicarboxylic acids and their anhydrides

, Germany, , ,

Production Method 15

1191-95-3

85462-16-4

872-50-4

Reaction Conditions

1.1 Solvents: Chloroform

Reference

Efficient synthesis of N-substituted lactams from (N-arylsulfonyloxy)amines and cyclic ketones

Hoffman, Robert V.; et al, Tetrahedron Letters, 1989, 30(32), 4207-10

Production Method 16

1119-48-8

872-50-4

Reaction Conditions

1.1 Catalysts: Silanol, trimethyl-, titanium(4+) salt Solvents: 1803415-30-6 ;  1 h, 120 °C

Reference

Hexaalkylguanidinium salts as ionic liquids-applications in titanium and aluminum alcoholate assisted synthesis

Arkhipova, Maria; et al, RSC Advances, 2014, 4(99), 56506-56517

Production Method 17

1119-48-8

872-50-4

Reaction Conditions

1.1 Reagents: 6-Aminohexanoic acid Solvents: 1,2-Dichloroethane

Reference

Titanium tetraisopropoxide-mediated lactamizations

Mader, Mary; et al, Tetrahedron Letters, 1988, 29(25), 3049-52

Production Method 18

15438-71-8

872-50-4

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ,  Sodium cyanoborohydride ;  1 - 2 d, rt

Reference

Sodium tris(trifluoroacetoxy)-borohydride

Gribble, Gordon W., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-3

Production Method 19

15438-71-8

872-50-4

Reaction Conditions

1.1 Reagents: Sodium cyanoborohydride Solvents: Trifluoroacetic acid

Reference

N-Methylation of amides and related compounds by reduction of methylols

Basha, Anwer; et al, Synthetic Communications, 1977, 7(8), 549-52

Production Method 20

872-50-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Polyethylene glycol Solvents: Toluene

Reference

N-alkylation of amides, imides, and lactams under phase-transfer catalysis

Cen, Junda; et al, Zhongguo Yiyao Gongye Zazhi, 1990, 21(5), 218-20

Production Method 21

872-50-4

Reaction Conditions

1.1 Reagents: Dimethyl carbonate Catalysts: Hexadecyltrimethylammonium bromide

Reference

Scope of the N-alkylation of amides and the C-alkylation of malonates by methyl formate and dimethyl carbonate

Ben Taleb, A.; et al, Journal of Molecular Catalysis, 1993, 84(2),

N-Methylpyrrolidone Raw materials

• Cyclobutanone
• 1-(hydroxymethyl)pyrrolidin-2-one
• Borate(1-),tetrafluoro-
• Methanamine, N-[[(4-nitrophenyl)sulfonyl]oxy]-
• 3-bromo-1-methylpyrrolidin-2-one
• Trimethyl phosphate
• N-Methylsuccinimide
• N-Methyl-4-aminobutyric Acid
• 2,5-dihydrofuran-2,5-dione
• 1-Methylpyrrolidine
• 1-Methylpyrrolidine-2-thione
• 5-[(1Z)-1-Hexen-1-ylthio]-3,4-dihydro-1-methyl-2H-pyrrolium

N-Methylpyrrolidone Preparation Products

• N-Methylpyrrolidone (872-50-4)

• 1. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 2. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 5. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolidines N-alkylpyrrolidines
• Solvents and Organic Chemicals Organic Solvents

Properties and Applications of N-Methylpyrrolidone (CAS No. 872-50-4)

N-Methylpyrrolidone (NMP), with the chemical formula C?H?NO, is a highly polar aprotic solvent that has garnered significant attention in the field of chemical and pharmaceutical research due to its unique physicochemical properties. Its CAS number, 872-50-4, identifies it as a well-characterized compound with a broad range of industrial and laboratory applications. NMP is renowned for its excellent solvency power, making it an indispensable solvent in various synthetic processes, particularly in polymer chemistry and pharmaceutical manufacturing.

The versatility of N-Methylpyrrolidone stems from its ability to dissolve a wide array of organic and inorganic compounds, including those that are poorly soluble in traditional solvents. This attribute has positioned it as a critical component in the synthesis of active pharmaceutical ingredients (APIs) and advanced materials. Recent advancements in green chemistry have further highlighted the importance of NMP as an eco-friendly solvent alternative, given its relatively low toxicity and high biodegradability compared to some conventional solvents.

In the pharmaceutical industry, N-Methylpyrrolidone plays a pivotal role in the formulation and purification of APIs. Its high boiling point and thermal stability make it suitable for use in high-temperature reaction conditions, while its low viscosity ensures efficient mass transfer during mixing and processing. Furthermore, NMP's compatibility with various functional groups allows for seamless integration into complex synthetic pathways, enhancing reaction yields and product purity.

One of the most compelling applications of N-Methylpyrrolidone is in the field of polymer science. It serves as an excellent solvent for both thermoplastic and thermosetting polymers, facilitating processes such as solution casting, spinning, and extrusion. The compound's ability to swell polymers without causing degradation makes it particularly valuable in the production of high-performance materials like specialty films, coatings, and adhesives. Recent research has demonstrated its efficacy in the development of biodegradable polymers, aligning with global efforts to reduce environmental impact.

Recent studies have also explored the potential of N-Methylpyrrolidone in drug delivery systems. Its ability to enhance the solubility of poorly water-soluble drugs has been leveraged to develop novel formulations that improve bioavailability and therapeutic efficacy. For instance, NMP-based nanomicelles have shown promise in targeted drug delivery, allowing for precise release profiles that optimize treatment outcomes. The compound's compatibility with hydrophobic drugs makes it an attractive choice for formulating oral and injectable medications.

The chemical stability of N-Methylpyrrolidone under various conditions has been extensively studied, reinforcing its reliability in industrial applications. Its resistance to hydrolysis and oxidation ensures consistent performance across diverse chemical environments. Additionally, NMP's low vapor pressure reduces evaporation losses during prolonged storage or processing, making it cost-effective for large-scale operations. These characteristics have solidified its reputation as a trusted solvent in both academic research and commercial production.

From an environmental perspective, efforts to minimize waste generation have led to innovative recycling strategies for N-Methylpyrrolidone. Advanced distillation techniques can recover unused or spent NMP from industrial processes, reducing both operational costs and environmental footprint. Furthermore, research into catalytic methods for converting NMP derivatives back into usable forms has opened new avenues for sustainable solvent management.

The future prospects of N-Methylpyrrolidone are closely tied to emerging trends in material science and pharmaceutical innovation. As industries seek sustainable alternatives to traditional solvents, NMP's favorable properties position it as a key player in next-generation technologies. For example, its use in electrochemical applications has been investigated due to its ability to support ionic transport without compromising electrode performance. Similarly, its role in energy storage devices continues to be explored as researchers aim to develop more efficient battery technologies.

In conclusion,N-Methylpyrrolidone (CAS No. 872-50-4) remains a cornerstone solvent in multiple scientific disciplines due to its exceptional solvency capabilities and environmental profile. Its applications span from pharmaceutical synthesis to advanced polymer manufacturing, underscoring its versatility and importance. As research progresses，the innovative uses of NMP are expected to expand，further cementing its status as a vital chemical compound in both industrial and academic settings.

• 2687-91-4(N-Ethylpyrrolidinone)
• 3470-99-3(1-Propylpyrrolidin-2-one)
• 6739-79-3(2-Oxo-1-pyrrolidinebutyramide)
• 55684-87-2(Pyrrolidinone, 1-methyl-)
• 14052-94-9(2-Pyrrolidinone,1-[4-(1-pyrrolidinyl)butyl]-)
• 3470-98-2(1-Butylpyrrolidin-2-one)
• 26138-58-9(1-Methyl-2-pyrrolidinone)
• 2687-44-7(N-Methyl-2-pyrrolidone)
• 30207-69-3(Pyrrolidinone, methyl-)
• 51013-18-4(2-Pyrrolidinone,methyl-)