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3-Bromopentane is a glass forming liquid used in the preparation of 2-(1-ethyl-propoxy)-isoindole-1,3-dione. Further, it is employed in organic synthesis.
Can be used to introduce the 3-pentyl (Pen) group for protection of the phenolic OH group of tyrosine residues in peptide synthesis. See Appendix 6. The Pen group can be introduced in the presence of NaH in DMF. In comparison with other common OH protecting groups, Pen is relatively stable to 50% TFA in dichloromethane and completely stable to 20% piperidine in DMF, but can be cleaved with HF in the presence of a cation scavenger, e.g. anisole or p-cresol: Terahedron Lett., 39, 7117 (1998).
Belter, R. K. Addition reactions of organometallic reagents to nitrogen trifluoride and enhanced alkyl-alkyl coupling by NF3. J. Fluorine Chem. 2015, 175, 110-113.
Sakaguchi, T.; Nakano, T.; Tominaga, S.; Hashimoto, T. Polycondensation of di- and tetrasubstituted dibromobenzenes for synthesis of poly(p-phenylene)s having alkoxy groups and gas permeability of membranes. Polym. J. 2015, 47, 362-368.
Hazard Statements: H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-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. 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 (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. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. 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