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18997-19-8 - Chloromethyl pivalate, 97% - Chloromethyl trimethylacetate - Pivaloyloxymethyl chloride - A11967 - Alfa Aesar

A11967 Chloromethyl pivalate, 97%

Número CAS
18997-19-8
Nombre Alternativo
Chloromethyl trimethylacetate
Pivaloyloxymethyl chloride

Tamaño Precio ($) Cantidad Disponibilidad
25g 25,80
100g 66,70
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Chloromethyl pivalate, 97%

MDL
MFCD00000884
EINECS
242-735-1

Propiedades químicas

Fórmula
C6H11ClO2
Peso molecular
150.60
Punto de ebullición
146-148°
Punto de inflamabilidad
40°(104°F)
Densidad
1.045
Índice de refracción
1.4170
Solubilidad
Miscible with most organic solvents. Immiscible with water.

Aplicaciones

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.

Notas

Incompatible with strong oxidizing agents.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H226-H314-H318

Flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Indicaciones de precaución: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
1560838
Clase de peligro
3
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2915.90
TSCA
Yes

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