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Useful protected pyrrole derivative which undergoes regioselective electrophilic substitution, e.g. Friedel-Crafts acylation, at the 3-position: Tetrahedron Lett., 22, 4899, 4901 (1981); Synthesis, 353 (1985) (review); J. Org. Chem., 48, 3214 (1983). The phenylsulfonyl group is readily cleaved by alkaline hydrolysis. For acylation followed by reduction as a route to 3-alkylpyrroles, see: J. Org. Chem., 64, 3379 (1999). See also 1-(Triisopropylsilyl)pyrrole, L13152./n
With a Grignard reagent, e.g. i-PrMgCl, transmetallation occurs at the 2-position, allowing access to 2-substituted derivatives by reaction with electrophiles: Org. Lett., 6, 293 (2004)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing 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 ON SKIN: Wash with plenty of soap and water. 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. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant