Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

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

A11967 Chloromethyl pivalate, 97%

CAS Number
18997-19-8
Synonyms
Chloromethyl trimethylacetate
Pivaloyloxymethyl chloride

Size Price ($) Quantity Availability
25g 22.77
100g 62.82
Add to Cart Add to Quote Request View Item

Chloromethyl pivalate, 97%

MDL
MFCD00000884
EINECS
242-735-1

Chemical Properties

Formula
C6H11ClO2
Formula Weight
150.60
Boiling Point
146-148°
Flash Point
40°(104°F)
Density
1.045
Refractive Index
1.4170
Solubility
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.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H314-H318-H226

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

Precautionary Statements: 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.

Other References

Beilstein
1560838
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2915.90
TSCA
Yes

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware