4-Nonanoylmorpholine

4-Nonanoylmorpholine

Names
IUPAC name 4-Nonanoylmorpholine
Other names 4-(1-Oxononyl)morpholine, N-Nonanoylmorpholine, 1-(4-Morpholino)-1-nonanone, 4-Morpholinenonylic acid, Pelargonic acid morpholide, Pelargonic morpholide, N-Morpholino nonanamide, 1-Morpholin-4-ylnonan-1-one, MPA, MPK
Identifiers
CAS Number	5299-64-9
ChemSpider	71509
Jmol interactive 3D	Image Image
PubChem	79182
InChI InChI=1S/C13H25NO2/c1-2-3-4-5-6-7-8-13(15)14-9-11-16-12-10-14/h2-12H2,1H3 Key: NBRDJXSTGSUITP-UHFFFAOYSA-N InChI=1/C13H25NO2/c1-2-3-4-5-6-7-8- 13(15)14-9-11-16-12-10-14/h2-12H2,1H3 InChI=1/C13H25NO2/c1-2-3-4-5-6-7-8-13(15)14-9-11-16-12-10-14/h2-12H2,1H3 Key: NBRDJXSTGSUITP-UHFFFAOYAS
SMILES CCCCCCCCC(=O)N1CCOCC1 O=C(N1CCOCC1)CCCCCCCC
Properties
Chemical formula	C13H25NO2
Molar mass	227.34 g/mol
Appearance	Liquid
Boiling point	310 to 315 °C (590 to 599 °F; 583 to 588 K)
Solubility in water	Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Nonanoylmorpholine (pelargonic acid morpholide, N-nonanoylmorpholine, MPK or МПК (for морфолид пеларгоновой кислоты), or MPA) is an amide of pelargonic acid and morpholine.

Properties

4-Nonanoylmorpholine was first synthetized in 1954 by L.M. Rice, from morpholine and chloroanhydride of pelargonic acid.

It is a liquid insoluble in water and soluble in polar organic solvents (e.g. acetone, propanol, and dimethyl formamide) and fats. Its volatility is 27 mg/m³ at 20 °C and 43 mg/m³ at 35 °C.

Uses

It is a used as a solvent in lachrymatory formulations containing CR gas or CS gas. It is reported to be effective against dogs and starts being effective in concentrations of over 20–40 mg.min/m³. It is considered very safe, with high differences between effective and toxic concentrations. At one time it was reportedly used as food seasoning with no reported adverse effects. However, its effectiveness when used alone is rather low even in the highest permitted concentration, so it is almost always used in combination with CR gas or CS gas, commonly referred to as tear gas. In that combination, this blend is effective even against dogs and people under influence of alcohol or other drugs. Its effect usually lasts for 15–30 minutes.

MPK blends with CR gas or CS gas are common personal self-defense chemical agents in Russia and Ukraine, but is virtually unknown elsewhere.

4-Nonanoylmorpholine has been reported to have insect repellent properties in Aedes aegypti mosquitoes.^[1]

Notes

1. Pherobase entry

References

• Collum D.B., Chen S.-C., Ganem B. (1978). "A new synthesis of amides and macrocyclic lactams" (PDF). Journal of Organic Chemistry 43 (22): 4393–4394(2). doi:10.1021/jo00416a040. Archived from the original (PDF) on June 11, 2007. Retrieved 2007-07-06.