18997-19-8

Basic information

• Product Name: Chloromethyl pivalate
• Synonyms: 2,2-dimethyl-propanoicacichloromethylester;POM;POM-CL;PIVALOYLOXYMETHYL CHLORIDE;PIVALIC ACID CHLOROMETHYL ESTER;TRIMETHYLACETIC ACID CHLOROMETHYL ESTER;2,2-DIMETHYLPROPIONIC ACID CHLOROMETHYL ESTER;CHLOROMETHYL TRIMETHYLACETATE
• CAS NO: 18997-19-8
• Molecular Formula: C₆H₁₁ClO₂
• Molecular Weight: 150.6
• EINECS: 242-735-1
• Product Categories: Pharmaceutical Intermediates;Phosgene Derivatives;Miscellaneous;Pharmaceutical Intermediate;Other Products;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;API
• Mol File: 18997-19-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: <-40°C
• Boiling Point: 146-148 °C(lit.)
• Flash Point: 104 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.045 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.45mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Miscible with most organic solvents. Immiscible with water.
• BRN: 1560838
• CAS DataBase Reference: Chloromethyl pivalate(CAS DataBase Reference)
• NIST Chemistry Reference: Chloromethyl pivalate(18997-19-8)
• EPA Substance Registry System: Chloromethyl pivalate(18997-19-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36-41-36/37/39
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 18997-19-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

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.

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.

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

Upstream product

• 74-97-5 chlorobromomethane 
• 19455-23-3 potassium pivalate 
• 1184-88-9 sodium pivalate 
• 49715-04-0 chlorosulfuric acid chloromethyl ester 
• 75-98-9 Trimethylacetic acid 
• 50-00-0 formaldehyd 
• 3282-30-2 pivaloyl chloride 
• 598-98-1 Methyl pivalate 

Downstream Products

• 4920-92-7 pivalic acid phenyl ester 
• 161715-24-8 tebipenem 
• 379229-61-5 [7-(benzyloxy)-5-hydroxy-4-oxoquinazolin-3(4H)yl]methyl pivalate 
• 944718-09-6 2,2-Dimethyl-propionic acid 6-methoxy-1-oxo-1,3-dihydro-isoindol-2-ylmethyl ester 
• 1011535-02-6 C₃₁H₄₄NPO₉ 
• 1011535-03-7 C₃₁H₄₄NPO₉CH₂ 
• 193002-24-3 7-benzyloxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one 
• 162599-64-6 pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(S)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate 
• 162599-64-6 pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(R)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate 
• 219709-48-5 4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine 
• 219709-47-4 4-S-pivaloyloxymethyl-5'-O-dimethoxytrityl-3'-O-tert-butyldimethylsilyl-4-thiouridine 
• 205928-47-8 2,2-Dimethylpropionic acid [7-benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester 
• 205928-46-7 (7-benzyl-3-[[(2,2-dimethylpropanoyl)oxy]methyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl 2,2-dimethylpropanoate 

Relevant articles and documents

Novel multifunctional acyloxyalkyl ester prodrugs of 5-aminolevulinic acid display improved anticancer activity independent and dependent on photoactivation

Multifunctional acyloxyalkyl ester prodrugs of 5-aminolevulinic acid in cancer cell lines inhibited the proteasome and induced apoptosis and heme synthesis. The most potent prodrug was butyryloxymethyl 5-amino-4-oxopentanoate (1a). The metabolically released formaldehyde from the prodrugs was the dominant factor affecting cell viability by a ROS-dependent mechanism and was responsible for rapid phosphorylation of H2AX, suppression of the cell survival protein c-myc, and transient elevation in the expression of p21. 1a, which differs from 2a by releasing butyric instead of pivalic acid, was a more potent inducer of heme and acetylated H4 expression and induced apoptosis through activation of caspase 9. 1a and 1b specifically increased the level of the photosensitizer protoporphyrin 9, leading to enhancement of cell death by photodynamic therapy (PDT). The advantage of these multifunctional prodrugs over 5-ALA is their greater potency in the non-PDT mechanism of cancer cell killing and their ability to also augment PDT.

Atmospheric oxidation mechanism of methyl pivalate, (CH3)3CC(O)OCH3

Smog chamber/FTIR techniques were used to study the Cl atom and OH radical initiated oxidation of methyl pivalate, (CH3)3CC(O)OCH3, in the presence of NOx in 700 torr of N2/O2 diluent at 296 K. The Cl atom initiated oxidation of methyl pivalate in the presence of 15-600 torr of O2 and 10-30 mtorr of NOx in 700 torr total pressure of N2 diluent at 296 K yielded HCHO, CO, acetone, CO2 and CH3OC(O)O2NO2. OH radical initiated oxidation of methyl pivalate in air produced acetone in a 51% yield. Flash photolysis-resonance fluorescence techniques were used to measure the rate constant for the reaction of OH radicals with methyl pivalate at 250-370 K. The rate constant showed a weak temperature dependence, increasing at both low and high temperature from a minimum value of about 1.2 × 10-12 cc/molecule-sec near room temperature. The data obtained were used to formulate a detailed mechanism describing the atmospheric oxidation of methyl pivalate. This mechanism gave predictions of the effects of methyl pivalate on O3 formation and other measures of reactivity that were in good agreement with results of environmental chamber experiments. It should be used in future airshed models to predict the effects of methyl pivalate emissions on air quality.

RODENTICIDAL NORBORMIDE ANALOGUES

The present invention relates to norbormide analogues having rodenticidal activity; rodenticidal compositions comprising the analogues; uses of the analogues as rodenticides; uses of the analogues in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.

PRODRUGS OF FUSED HETEROCYCLIC INHIBITORS OF D-AMINO ACID OXIDASE

The invention relates to prodrugs of fused heterocyclic inhibitors of D-amino oxidase (DAAO) and methods of treating diseases and conditions, wherein modulation of D-amino acid oxidase activity, D-serine levels, D-serine oxidative products and NMDA receptor activity in the nervous system of a mammalian subject is effective.