2687-96-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Lauryl-2-pyrrolidone is used as a chemical penetration enhancer for melatonin, facilitating the absorption and bioavailability of this hormone in the body. Its ability to enhance the permeability of melatonin can be beneficial in the development of drug formulations and delivery systems.
Used in Material Science:
1-Lauryl-2-pyrrolidone is used as an exfoliating agent in the preparation of few-layered flakes of molybdenum disulfide (MoS2) through liquid phase exfoliation of bulk MoS2 powder. This application highlights its utility in the development of advanced materials with improved properties for various applications, such as electronics and energy storage.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C16H31NO/c1-2-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16(17)18/h2-15H2,1H3

Synthetic route

1-bromo dodecane (112-29-8) + 1-dodecylbromide (143-15-7) → 1-dodecyl-2-pyrrolidinone (2687-96-9)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide	91%

2-pyrrolidinon (616-45-5) + 1-dodecylbromide (143-15-7) → 1-dodecyl-2-pyrrolidinone (2687-96-9)

Conditions	Yield
With tetrabutylammomium bromide In cyclohexane; water; ethyl acetate; toluene	80%

4-butanolide (96-48-0) + n-Dodecylamine (124-22-1) → 1-dodecyl-2-pyrrolidinone (2687-96-9)

Conditions	Yield
at 250℃;
at 250 - 270℃;

2-pyrrolidinon (616-45-5) + 1-chlorododecane (112-52-7) → 1-dodecyl-2-pyrrolidinone (2687-96-9)

Conditions	Yield
With sodium In ethanol for 6h; Heating;

n-Dodecylamine (124-22-1) → 1-dodecyl-2-pyrrolidinone (2687-96-9)

Conditions	Yield
	40.7 g (80.3%)

1-dodecyl-2-pyrrolidinone (2687-96-9) → 1-dodecyl-pyrrolidine (2915-94-8)

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 65℃; for 1h;	97%
With lithium dimethylamino borohydride In tetrahydrofuran at 65℃; for 2h;	96%

1-dodecyl-2-pyrrolidinone (2687-96-9) + nitromethane (75-52-5) → 1-Dodecyl-2-[1-nitro-meth-(E)-ylidene]-pyrrolidine

Conditions	Yield
With sodium methylate; dimethyl sulfate

1-dodecyl-2-pyrrolidinone (2687-96-9) + 2-chloro-ethanol (107-07-3) → 1-dodecyl-1-(2-hydroxy-ethyl)-2-oxo-pyrrolidinium; chloride

Conditions	Yield
In acetonitrile for 6h; Heating;

1-dodecyl-2-pyrrolidinone (2687-96-9) → C-(1-Dodecyl-pyrrolidin-2-yl)-methylamine (140237-06-5, 140237-07-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethyl sulfate, NaOMe 2: H2 / Raney Ni View Scheme

1-dodecyl-2-pyrrolidinone (2687-96-9) → C-((S)-1-Dodecyl-pyrrolidin-2-yl)-methylamine (140237-06-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethyl sulfate, NaOMe 2: H2 / Raney Ni View Scheme

1-dodecyl-2-pyrrolidinone (2687-96-9) → C-((R)-1-Dodecyl-pyrrolidin-2-yl)-methylamine (140237-07-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethyl sulfate, NaOMe 2: H2 / Raney Ni View Scheme

1-dodecyl-2-pyrrolidinone (2687-96-9) → N-((S)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide (139095-75-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethyl sulfate, NaOMe 2: H2 / Raney Ni 4: dimethylformamide / 2 h / -10 - 20 °C View Scheme

1-dodecyl-2-pyrrolidinone (2687-96-9) → N-((R)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide (140237-05-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethyl sulfate, NaOMe 2: H2 / Raney Ni 4: dimethylformamide / 2 h / -10 - 20 °C View Scheme

1-dodecyl-2-pyrrolidinone (2687-96-9) + 2,6-diisopropylphenyl isocyanate (28178-42-9) → N-[2,6-bis(1-methylethyl)phenyl]-1-dodecyl-2-oxo-3-pyrrolidine carboxamide (147750-31-0)

Conditions	Yield
With lithium diisopropyl amide

1-dodecyl-2-pyrrolidinone (2687-96-9) → C16H31NO*H2O2

Conditions	Yield
With dihydrogen peroxide In water at 60℃;

Upstream product

• 96-48-0 4-butanolide 
• 124-22-1 n-Dodecylamine 
• 112-29-8 1-bromo dodecane 
• 143-15-7 1-dodecylbromide 
• 616-45-5 2-pyrrolidinon 
• 112-52-7 1-chlorododecane 

Downstream Products

• 147750-31-0 N-[2,6-bis(1-methylethyl)phenyl]-1-dodecyl-2-oxo-3-pyrrolidine carboxamide 
• 140237-05-4 N-((R)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 
• 139095-75-3 N-((S)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 

Relevant academic research and scientific papers

BIFUNCTIONAL COMPOUNDS USEFUL AS LIGANDS OF URANIUM (VI), METHODS OF SYNTHESISING SAME AND USES THEREOF

New compounds which meet general formula (I): where: m=0, 1 or 2;R1 and R2=a C6 to C12, straight-chain or branched, hydrocarbon group;R3=H, a C1 to C12, straight-chain or branched, hydrocarbon group, optionally comprising one or more heteroatoms; a C3 to C8 monocyclic hydrocarbon group, optionally comprising one or more heteroatoms, or a monocyclic (hetero)aryl group;or else R2 and R3 together form a —(CH2)n— group where n=1 to 4;R4=a C2 to C8, straight-chain or branched, hydrocarbon group, or a monocyclic aromatic group;R5=H, or a C1 to C12, straight-chain or branched, hydrocarbon group.

Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts

For the purpose of developing new disinfectants and antiseptics, we searched for compounds having high bactericidal activity against gram-positive bacteria, gram-negative bacteria, and fungi. Three different series of quaternary imidazolium and pyrrolidinonium salts were synthesized: series A (1-alkyl-3-methylimidazolium chlorides and bromides); series B (1-alkyl-2-methyl-3-hydroxyethylimidazolium chlorides); and series C (N-alkyl-N-hydroxyethylpyrrolidinonium). Series B and C were newly designed. These three series were tested to evaluate their antibacterial and antifungal properties for the first time. Seven microbial strains were used in the study: Escherichia coli KCTC1924, Salmonella typhimurium KCTC1926, Staphylococcus aureus 209 KCTC1916, Staphylococcus aureus R209 KCTC1928, Bacillus subtilis KCTC1914, Candida albicans KCTC1940, and Chlorella regularis. The antimicrobial efficiency was measured by bacterial and fungal growth inhibition expressed as minimal inhibitory concentration (MIC) values. Series A and B imidazolium salts had very good antimicrobial activity against the examined Gram-negative bacteria, Gram-positive bacteria, and fungi. Also the pyrrolidinonium salt was found to have low MIC for some of tested microorganisms. The antibacterial and antifungal active properties of the salts depend upon the structure of functional groups and the alkyl chain length in the imidazolium and pyrrolidinonium ring. Among the synthesized quaternary imidazolium and pyrrolidinonium salts, the imidazolium salts containing a long alkyl chain and the introduction of a hydroxyethyl chain and methyl group into the imidazolium ring structure leads to broad spectrum active antimicrobial agents which not only have bacteriostatic properties but could be powerful bactericides.

N-allyl-lactams as crystallization inhibitors

Crystallization of active material in spraying of an aqueous solution of certain specified fungicides is retarded by incorporation therein of an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 6 to 18 carbon atoms and n represents the numbers 3, 4 or 5.

N-alkyl-lactams as crystallization inhibitors

In the spraying of an aqueous liquor comprising at least one of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol and 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol, the improvement which comprises including in the liquor an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 8 to 18 carbon atoms and n represents the numbers 3, 4 or 5,

Solid formulations

New solid formulations of A) at least one agrochemical active compound, B) at least one additive from the groups mentioned in the description, C) at least one dispersant, D) at least one carrier and E) if appropriate, further active compounds and/or additives, a process for preparing the solid formulations and their use for treating plants. A new device for preparing new granules.

Composition comprising an oxygenated cholesterol and use thereof for topical treatment of diseases

The invention is directed to a pharmaceutical composition comprising an oxygenated cholesterol and a penetration-enhancing agent which is useful for topical application to the skin of a patient suffering from a proliferative skin disease characterized by geminative cells having a rapid rate of replication, e.g. psoriasis. The composition comprises an effective amount for the inhibition of germinative cell mitosis of an oxygenated cholesterol, e.g. 26-hydroxycholesterol, or a pharmaceutically effective derivative thereof e.g. an ester or ether. The invention is further directed to a method of treating a patient suffering from said skin disease comprising applying to the effected skin said therapeutic composition. The invention is also directed to the topical application of these compositions to the skin to decrease inflammation.

Method of improved pest control

The disclosure describes a method for improved plant pest control comprising contacting a plant or plant pest with a composition comprising an effective amount of a plant pesticide and an effective delivery enhancing amount of compound having the structural formula STR1 wherein R' is H or a lower alkyl group having 1-4 carbon atoms, m is 3-7, n is 0-17 and R is --CH3, STR2 where R" is H or halogen, with the proviso that if m is 3 and R is CH3, then n is 5-17. Typical plant pesticides include insecticides, fungicides, herbicides, rodenticides, nematicides molluscicides and acaricides. The preferred penetration enhancing compound is 1-n-dodecylaza cycloheptan-2-one.

Tick repellents. II: N-substituted azacyclopentanones and azacyclopentenones

Several N-substituted azacyclopentanones were synthesized and evaluated as repellents for the brown dog tick Rhipicephalus sanguineus. Several of these compounds were more effective in our test system than were the standard repellents, N,N-dimethyl-m-toluamide and butopyranoxyl.