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141186

Sigma-Aldrich

Chloromethyl pivalate

97%

Synonym(s):

POM-Cl, Pivaloyloxymethyl chloride

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25 G
$57.10
100 G
$90.10

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
form:
liquid
assay:
97%

$57.10

In StockDetails

Request a Bulk Order

Quality Level

200

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.)

functional group

chloro
ester

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[1]. It undergoes acylation reaction with 9-(2-phosphonylmethoxyethyl)adenine (PMEA) to yield bis(pivaloyloxymethyl) PMEA[2].

Application

Chloromethyl pivalate was used in the synthesis of pivaloyloxy methyl ester of ofloxacin as prodrug[3]. It was used as the reagent during the synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis[4].

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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Certificates of Analysis (COA)

Lot/Batch Number
STBJ9969
STBH3189
STBD0426V
1369803
04218CJ

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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
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
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
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

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