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Protection of amines as their tetrachlorophthalimide derivatives, by reaction with the anhydride in the presence of triethylamine, has been found to be useful in oligosaccharide chemistry. The group is stable to a wide range of reagents but can be selectively cleaved with ethylenediamine at lower temperatures than for the parent phthalimide derivatives; in particular, carboxylic esters are not cleaved under these conditions.
Wilfred Howe, A.F.O.M., M.R.C.G.P.; Katherine M. Venables, M.Sc., M.R.C.P.; Michael D. Topping, Ph.D.; Michael B. Dally, M.R.A.C.P.; Rosemarie Hawkins, S.R.N.; J.Stephen Law, M.D.; Anthony J.Newman Taylor, M.Sc., M.R.C.P. Tetrachlorophthalic anhydride asthma: evidence for specific IgE antibody Journal of Allergy and Clinical Immunology. 1983, 71 (1), 5-11.
Gary M. Liss, MD, MS, FRCPC.; David Bernstein, MD.; Leon Genesove, MD, FRCPC.; Jaan O. Roos, MD, FRCPC.; Janet Lim, MD. Assessment of risk factors for IgE-mediated sensitization to tetrachlorophthalic anhydride. Journal of Allergy and Clinical Immunology. 1993, 92 ( 237-247),.
Protection of amines as their tetrachlorophthalimide derivatives, by reaction with the anhydride in the presence of triethylamine, has been found to be useful in oligosaccharide chemistry. The group is stable to a wide range of reagents but can be selectively cleaved with ethylenediamine at lower temperatures than for the parent phthalimide derivatives; in particular, carboxylic esters are not cleaved under these conditions: J. Am. Chem. Soc., 117, 3302 (1995); J. Org. Chem., 61, 432 (1996).
Hazard Statements: H317-H318-H334-H350
May cause an allergic skin reaction. Causes serious eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause cancer.
Precautionary Statements: P201-P202-P261-P272-P280g-P281-P285-P302+P352-P304+P341-P305+P351+P338-P308+P313-P310-P333+P313-P342+P311-P363-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Avoid breathing dust/fume/gas/mist/vapours/spray. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. Use personal protective equipment as required. In case of inadequate ventilation wear respiratory protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: If breathing is difficult, 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. IF exposed or concerned: Get medical advice/attention. Immediately call a POISON CENTER or doctor/physician. If skin irritation or rash occurs: If experiencing respiratory symptoms: Call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant