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

A11967 Chloromethyl pivalate, 97%

CAS-Nummer
18997-19-8
Synonyme
Chloromethyl trimethylacetate
Pivaloyloxymethyl chloride

Größe Preis ($) Menge Verfügbarkeit
25g 22,77
100g 62,82
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Chloromethyl pivalate, 97%

MDL
MFCD00000884
EINECS
242-735-1

Chemische Eigenschaften

Formel
C6H11ClO2
Molmasse
150.60
Siedepunkt
146-148°
Flammpunkt
40°(104°F)
Dichte
1.045
Brechungsindex
1.4170
Löslichkeit
Miscible with most organic solvents. Immiscible with water.

Anwendungen

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.

Bemerkungen

Incompatible with strong oxidizing agents.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318-H226

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

Sicherheitshinweise: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1560838
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2915.90
TSCA
Yes

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