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Morpholine is a common additive for pH adjustment in both fossil fuel and nuclear power plant steam systems. It is widely used in organic synthesis as a building block in the preparation of the antibiotic linezolid, the anticancer agent gefitinib and the analgesic dextromoramide. It is also used as a solvent in chemical reactions and in the preparation of enamines. Further, it serves as a chemical emulsifier in the process of waxing fruit.
Reagent for the cleavage of Fmoc protecting groups in peptide synthesis (see 9-Fluorenylmethyl chloroformate, A11683): J. Am. Chem. Soc., 92, 5748 (1970); J. Org. Chem., 37, 3404 (1972). See Appendix 6 for peptide reagents.
In the Kindler modification of the Willgerodt reaction, aryl ketones are converted to ω-arylalkanoic acids by reaction with sulfur and an amine, usually morpholine: Org. Synth. Coll., 9, 99 (1998); reviews: Org. React., 3, 83 (1946); Synthesis, 358 (1975).
Lithium morpholide adds to aromatic aldehydes at low temperature, a useful means for the protection of the aldehyde group in lithiations: Tetrahedron Lett., 25, 4213 (1981); J. Org. Chem., 48, 2356 (1983).
Chlorination with hypochlorite gives N-chloromorpholine, a useful reagent in strongly acid media for the selective chlorination of activated aromatics: Org. Synth. Coll., 8, 167 (1993), and references therein.
Chen, D.; Miao, H.; Zou, J.; Cao, P.; Ma, N.; Zhao, Y.; Wu, Y. Novel Dispersive Micro-Solid-Phase Extraction Combined with Ultrahigh-Performance Liquid Chromatography-High-Resolution Mass Spectrometry To Determine Morpholine Residues in Citrus and Apples. J. Agric. Food. Chem. 2015, 63 (2), 485-492.
Ye, L.; Zhai, L.; Fang, J.; Liu, J.; Li, C.; Guan, R. Synthesis and characterization of novel cross-linked quaternized poly (vinyl alcohol) membranes based on morpholine for anion exchange membranes. Solid State Ionics 2013, 240, 1-9.
Hazard Statements: H226-H302-H312-H332-H314
Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes severe skin burns and eye damage.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.