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141186

Sigma-Aldrich

Chloromethyl pivalate

97%

Synonym(s):

POM-Cl, Pivaloyloxymethyl chloride

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About This Item

Linear Formula:
(CH3)3CCOOCH2Cl
CAS Number:
18997-19-8
Molecular Weight:
150.60
Beilstein/REAXYS Number:
1560838
EC Number:
242-735-1
MDL number:
MFCD00000884
UNSPSC Code:
12352100
PubChem Substance ID:
24848492
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.417 (lit.)

bp

146-148 °C (lit.)

density

1.045 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)C(=O)OCCl

InChI

1S/C6H11ClO2/c1-6(2,3)5(8)9-4-7/h4H2,1-3H3

InChI key

GGRHYQCXXYLUTL-UHFFFAOYSA-N

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General description

Chloromethyl pivalate reacts with sodium salt of sulbactam to yield sulbactam pivoxil. It undergoes acylation reaction with 9-(2-phosphonylmethoxyethyl)adenine (PMEA) to yield bis(pivaloyloxymethyl) PMEA.

Application

Chloromethyl pivalate was used in the synthesis of pivaloyloxy methyl ester of ofloxacin as prodrug. It was used as the reagent during the synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

104.0 °F - closed cup

flash_point_c

40 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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L S Changov et al.
Farmaco (Societa chimica italiana : 1989), 55(2), 134-135 (2000-04-27)
Sulbactam pivoxil, a prodrug of the beta-lactamase inhibitor sulbactam, was prepared in high yield by reacting the sodium salt of sulbactam with chloromethyl pivalate in a polar solvent, then diluting the reaction mixture with water and isolating the product by
J E Starrett et al.
Antiviral research, 19(3), 267-273 (1992-09-11)
9-(2-Phosphonylmethoxyethyl)adenine (PMEA; 1) was acylated with chloromethyl pivalate to afford bis(pivaloyloxymethyl) PMEA (2). The ester prodrug demonstrated enhanced in vitro potency against HSV-2 greater than 150-fold higher than the parent compound. The antiviral activity of 2 was 50-fold better than
Y Maeda et al.
Biological & pharmaceutical bulletin, 16(6), 594-599 (1993-06-01)
We newly synthesized a pivaloyloxymethyl ester of ofloxacin (OFLX-PVM) as prodrug in order to avoid the chelate formation between new quinolone and metal cations such as Al3+, Mg2+, Ca2+, or Fe2+ in the gastrointestinal tract. This compound was rapidly hydrolyzed
Farman Ullah et al.
Synthesis, 44(16), doi:10-doi:10 (2012-01-01)
A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulat-ed, tricyclic sultam library, utilizing a Heck-aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vi-nylsulfonamides with batch microwave heating followed by a one-pot, sequential

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