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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-H311-H314-H331-H335-H373
Flammable liquid and vapour. Harmful if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. Toxic if inhaled. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant