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

A11967 Chloromethyl pivalate, 97%

Numéro de CAS
18997-19-8
Synonymes
Chloromethyl trimethylacetate
Pivaloyloxymethyl chloride

Conditionnement Prix ($) Quantité Disponibilité
25g 25,80
100g 66,70
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Chloromethyl pivalate, 97%

MDL
MFCD00000884
EINECS
242-735-1

Propriétés chimiques

Formule
C6H11ClO2
Poids moleculaire
150.60
Point d'ébullition
146-148°
Point d'éclair
40°(104°F)
Densité
1.045
Indice de réfraction
1.4170
Solubilité
Miscible with most organic solvents. Immiscible with water.

Applications

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.

Notes

Incompatible with strong oxidizing agents.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H314-H318

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

Mentions de prudence: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. 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.

Autres références

Beilstein
1560838
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2915.90
TSCA
Yes

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire