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Extensively finds applications as a base, a nucleophile and a solvent. Used for the production of dipiperidinyl dithiuram tetrasulfide, which is used as a rubber vulcanization accelerator. It is commonly used in solid phase peptide synthesis (F-MOC Chemistry) and in chemical degradation reactions (sequencing of DNA). Used in making rubber, curing epoxy resins and in fine chemicals, and pharmaceuticals.
Rubiralta, M.; Giralt, E.; Diez, A. Piperidine: structure, preparation, reactivity, and synthetic applications of piperidine and its derivatives; Elsevier Science: Burlington, 2013; 460 p.
Srivastava, K.; Davis, M. A comparative examination of two Fmoc removal reagents for process improvement to produce peptide drugs. Adv. Exp. Med. Biol. 2009, 611, 585-91.
Base catalyst in the Doebner modification of the Knoevenagel condensation; see Malonic acid, A11526.
Widely used for cleavage of Fmoc protecting groups: J. Org. Chem., 52, 1197 (1987); Tetrahedron Lett., 34, 6135 (1993). See Appendix 6.
For preparation of the piperidine enamine of cyclooctanecarboxaldehyde, and its subsequent use in the synthesis of spirohexadienones, see: Org. Synth. Coll., 7, 473 (1990).
Hazard Statements: H225-H311-H314-H331-H335-H373
Highly flammable liquid and vapour. 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-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-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 Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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. 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