105-48-6

Usage

Uses

Used in Pharmaceutical Industry:
Isopropyl chloroacetate is used as a reactant in the design, synthesis, and 3D-QSAR analysis of novel oxadiazolones. These oxadiazolones act as protoporphyrinogen oxidase inhibitors, which are significant in the pharmaceutical industry for their potential applications in developing new drugs and therapies.
Used in Chemical Synthesis:
Isopropyl chloroacetate is utilized in the synthesis of various chemicals, contributing to the development of new compounds and materials with diverse applications across different industries. Its versatility as a reactant makes it a valuable component in the chemical manufacturing process.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Isopropyl chloroacetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

InChI:InChI=1/C5H9ClO2/c1-3(2)4(6)5(7)8/h3-4H,1-2H3,(H,7,8)/p-1

Upstream product

• 13048-66-3 glycine isopropyl ester 
• 22136-61-4 isopropyl diazoacetate 
• 187737-37-7 propene 
• 7637-07-2 boron trifluoride 
• 79-11-8 chloroacetic acid 
• 96-34-4 methyl chloroacetate 
• 67-63-0 isopropyl alcohol 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 76508-37-7 (1,1,3-Trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid isopropyl ester 
• 79-11-8 chloroacetic acid 
• 67-63-0 isopropyl alcohol 
• 83769-17-9 3-Propyl-oxirane-2-carboxylic acid isopropyl ester 
• 2881-29-0 4,4-diethyl-2-oxomorpholinium chloride 
• 92723-25-6 isopropyl 2-(3-methoxyphenoxy)acetate 
• 2073-72-5 1,2-Bis-(isopropyloxycarbonyl-methoxy)-3,4,5,6-tetrachlor-benzol 
• 91446-69-4 2-Methoxy-3,4,5,6-tetrachlor-phenoxy-essigsaeure-isopropylester 
• 91495-18-0 2-Methoxy-4,5-dichlor-phenoxy-essigsaeure-isopropylester 
• 91555-20-3 isopropyl 2-(4-methoxyphenoxy)acetate 
• 13195-64-7 diisopropyl malonate 
• 58942-23-7 isopropyl 2-hydroxy-3-(4-cyclohexylphenyl)-3-butenoate 
• 1100708-16-4 isopropyl 5,6-diaza-4-methyl-7-oxo-2,2,6-triphenylsipro[2,4]hept-4-ene-1-carboxylate 

Relevant academic research and scientific papers

Synthesis and characterization of task-specific ionic liquids possessing two Broensted acid sites

Task-specific ionic liquids possessing two Broensted acid sites with -COOH, HSO-4, or H2PO-4 groups have been designed, synthesized, and characterized. Under mild conditions and without any additional organic solvent, the esterification of isopropanol by chloroacetic acid could be carried out in these new task-specific ionic liquids. In comparison with most of acidic ionic liquids in current use, these ionic liquids are halogen free and more environmentally benign as media and catalysts. Copyright Taylor & Francis Group, LLC.

Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors

A new series of triazolophthalazine derivatives was designed and synthesized as topoisomerase II (Topo II) inhibitors and DNA intercalators. The synthesized derivatives were evaluated in vitro for their cytotoxic activities against three human cancer cell lines: HepG2, MCF-7, and HCT-116 cells. Compound IXb was the most potent counterpart with IC50 values of 5.39 ± 0.4, 3.81 ± 0.2, and 4.38 ± 0.3 μM, as it was about 1.47, 1.77, and 1.19 times more active than doxorubicin (IC50 = 7.94 ± 0.6, 6.75 ± 0.4, and 5.23 ± 0.3 μM) against HepG2, MCF-7, and HCT-116 cells, respectively. Additionally, the binding affinity of the synthesized compounds toward the DNA molecule was assessed using the DNA/methyl green assay. Compound?IXb showed an excellent DNA binding affinity with an IC50 value of 27.16 ± 1.2 μM, which was better than that of the reference drug doxorubicin (IC50 = 31.02 ± 1.80 μM). Moreover, compound IXb was the most potent member among the tested compounds when investigated for their Topo II inhibitory activity. Furthermore, compound IXb induced apoptosis in HepG2 cells and arrested the cell cycle at the G2/M phase. Additionally, compound IXb showed Topo II poisoning effects at 2.5 μM and Topo II catalytic inhibitory effects at 5 and 10 μM. Finally, molecular docking studies were carried out against the DNA–Topo II complex and DNA, to investigate the binding patterns of the designed compounds.

New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential

Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (SN2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. The evaluation of the compounds’ potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 μg mL?1

Synthesis, in silico Study and Antimicrobial Evaluation of New Diesters Derived from Phthaloylglycine

New diesters derived from phthaloylglycine (7a-7i) were synthesized and their structures characterized by infrared, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The compounds were evaluated in an in silico study, which demonstrated positive features indicating a possible drug candidate. The diesters showed antifungal activity ranging from moderate to strong against strains of Candida. Compounds 7a, 7b, 7c, 7e and 7i had a moderate minimum inhibitory concentration (MIC) of 1024 μg mL?1 against all fungal strains, while 7h showed a very good MIC of 256 μg mL?1 against Candida albicans, Candida parapsilosis and Candida krusei and 64 μg mL?1 against Candida tropicalis. However, only 7h and 7i were able to inhibit bacterial growth of strains of Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa and Escherichia coli with an MIC of 1024 μg mL?1

A pure Radix Salviae Miltiorrhizae usually different propyl ester synthesis method (by machine translation)

The invention relates to a pure Radix Salviae Miltiorrhizae usually different propyl ester synthesis method, the method comprising the protocatechuic aldehyde as a starting raw material, after phenmethyl protection phenol hydroxy, Darzens ring oxidation, and then through the arrowhead class catalyst/hydrogen or Raney nickel/hydrogen catalytic reduction, to obtain pure Radix Salviae Miltiorrhizae usually different propyl ester. The method of the invention the synthetic product purity can be up to 98%, a yield of 55%. And the synthesis method of the invention, and is simple, short route, the productive rate is high, and is suitable for large-scale industrial production. (by machine translation)

Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions

In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.

A method for preparing 2, 4 - dichlorophenoxyacetic acid (by machine translation)

The invention provides a 2, 4 - dichlorophenoxyacetic acid preparation method, comprises the following steps, first alcohol and a halogenated acetic acid after the reaction, to obtain halogenated acetate; the 2, 4 - dichlorophen after reaction with the alkali, to obtain 2, 4 - II [...]; then the above-mentioned step to obtain the halo acetate with 2, 4 - dichlorophen salt, to obtain 2, 4 - dichlorophenoxy ester; then obtained the above-mentioned step 2, 4 - dichlorophenoxy ester hydrolytic reaction, to obtain the 2, 4 - dichloro acid and alcohol; finally the above-mentioned step returns mellowly obtained is used in the aforesaid step, recycling; the alcohol is C atom number greater than or equal to 2 alcohol. The invention adjusts the process route, from the improved on the basis of, the reaction process is cleaning, of the small amount of waste water, hydrolysis few by-products, high purity of the product, the conversion and yield higher; and process raw materials can be recycled, is suitable for large-scale industrial production. (by machine translation)

CYCLIC PHOSPHATE SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to Cyclic Phosphate Substituted Nucleoside Derivatives of Formula (I), and pharmaceutically acceptable salts thereof, wherein A, B, Q, V, R1, R2 and R3 are as defined herein. The present invention also relates to compositions comprising a Cyclic Phosphate Substituted Nucleoside Derivative, and methods of using the Cyclic Phosphate Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.

A simple criterion for gas chromatography/mass spectrometric analysis of thermally unstable compounds, and reassessment of the by-products of alkyl diazoacetate synthesis

Rationale: A principal limitation of gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) is the thermal instability of analytes. We propose that the injector and column temperatures should not exceed the atmospheric pressure boiling point, without decomposition, of the highest homologue of the series being analyzed, instead of the time-consuming procedure of obtaining chromatograms using different temperatures. Methods: A series of thermally unstable diazocarbonyl compounds, alkyl diazoacetates (predicted limit of stability approx. 140 °C, the boiling point of ethyl diazoacetate), was selected for GC/MS analysis using standard equipment. Different GC separation conditions were selected so that the retention temperatures of target compounds were both below and above 140°C. Results: Analyzing alkyl diazoacetates within their thermal stability range permitted reanalysis of their typical synthesis by-products. No dialkyl fumarate or maleate impurities, principal decomposition products which have often been reported previously, were found. Instead, alkyl esters of glycolic acid nitrate, O2NOCH 2CO2R, and 'pseudo-dimeric' products, ROCO[C 2H3NO]CO2R, were discovered for the first time. Conclusions: Avoiding the decomposition of thermally unstable organic compounds during GC and/or GC/MS analysis requires estimating their degradation temperature limits. This limit can be estimated as being equal to the atmospheric pressure boiling point of the highest homologue in the homologous series under consideration that does not decompose on boiling. Copyright

Preparation of esters of mono- or dicarboxylic non-aromatic and aromatic acids

The present invention relates to a method for preparing a carboxylic acid ester, wherein a carboxylic acid and/or a salt thereof is reacted with an alcohol in the presence of hydrogen chloride (HCl) and water to form the carboxylic acid ester, wherein the reaction is carried out using a starting reaction system wherein the molar ratio of HCl to carboxylic acid is at least 0.075 : 1 and the molar ratio of water to carboxylic acid is at least 0.25 : 1.