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Chloromethyl pivalate acts as an intermediate in the synthesis of active pharmaceutical ingredients. It is also involved in the acylation reaction with 9-(2-phosphonylmethoxyethyl)adenine. It serves as a protecting reagent used for the N-protection of amines. It is also employed in the preparation of pivaloyloxy methyl ester of ofloxacin as a prodrug. Further, it is used to prepare sulbactam pivoxil by reaction with sodium salt of sulbactam. In addition to this, it is used as a reagent during the synthesis of an isoindoline-annulated and continuous-flow organic synthesis.
Reagent for the N-protection of amines, e.g. adenine in the presence of K2CO3 in DMF, as pivaloyloxymethyl (Pom) derivatives, which have been found useful in the synthesis of sensitive nucleosides. The Pom group is cleaved in mild base, e.g. methanolic ammonia: J. Am. Chem. Soc., 89, 5439 (1967).
Imamoto, T.; Horiuchi, Y.; Hamanishi, E.; Takeshita, S.; Tamura, K.; Sugiya, M.; Yoshida, K. Utilization of optically active secondary phosphine-boranes: synthesis of P-chiral diphosphines and their enantioinduction ability in rhodium-catalyzed asymmetric hydrogenation. Tetrahedron 2015, 71 (37), 6471-6480.
Bru?cher, K.; Gra?wert, T.; Konzuch, S.; Held, J.; Lienau, C.; Behrendt, C.; Illarionov, B.; Maes, L.; Bacher, A.; Wittlin, S.; Mordmüller, B.; Fischer, M.; Kurz, T. Prodrugs of Reverse Fosmidomycin Analogues. J. Med. Chem. 2015, 58 (4), 2025-2035.
Hazard Statements: H226-H302-H312-H314-H332-H335
Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation.
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