535-13-7

Usage

Uses

Used in Polymer Synthesis:
Ethyl 2-chloropropionate is used as an initiator for the synthesis of poly(2-(diethylamino)ethyl methacrylate) and poly(N-isopropylacrylamide) via atom transfer radical polymerization. This application takes advantage of its ability to initiate the polymerization process, leading to the formation of specific polymers with desired properties.
Used in End-functionalized Polymer Synthesis:
In the field of polymer chemistry, Ethyl 2-chloropropionate is also used in the synthesis of end-functionalized poly(N-isopropylacrylamide) with a pyrenyl group. This application highlights its role in creating polymers with specific functional groups, which can be further utilized in various applications such as drug delivery, sensors, and other advanced materials.
Used in Chemical Industry:
Ethyl 2-chloropropionate, with its chemical properties as a clear colorless liquid and a pleasant odor, finds use in the chemical industry for various purposes. Its insolubility in water and heavier vapors compared to air make it suitable for specific reactions and processes that require such characteristics.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Ethyl 2-chloropropionate is a halogenated 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

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Shipping

UN2935 Ethyl 2-chloropropionate, Hazard Class: 3; Labels: 3-Flammable liquid.

Incompatibilities

Flammable liquid; forms explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and reducing agents. Esters are generally incompatible with nitrates. Moisture may cause hydrolysis or other forms of decomposition. Esters react with acids releasing heat in addition to alcohols and acids. Contact with caustic solutions generate heat. Contact with esters with alkali metals and hydrides releases flammable hydrogen.

InChI:InChI=1/C5H9ClO2/c1-3-8-5(7)4(2)6/h4H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 91-22-5 quinoline 
• 760-11-2 O-chlorosulfonyl-lactic acid ethyl ester 
• 6111-99-5 ethyl diazoalaninate 
• 128-09-6 N-chloro-succinimide 
• 105-37-3 Ethyl propionate 
• 97-64-3 ethyl 2-hydroxypropionate 
• 64-17-5 ethanol 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 687-47-8 (S)-Ethyl lactate 
• 142-04-1 aniline hydrochloride 
• 628-13-7 pyridine hydrochloride 
• 98-88-4 benzoyl chloride 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 

Downstream Products

• 63909-12-6 2-piperidino-propionic acid ethyl ester 
• 28578-16-7 3-benzo[1,3]dioxol-5-yl-2-methyl-oxiranecarboxylic acid ethyl ester 
• 97-64-3 ethyl 2-hydroxypropionate 
• 42411-41-6 3-ethyl-2-chloro-pentan-3-ol 
• 7737-40-8 ethyl 2-ethoxypropionate 
• 71662-27-6 2-butyryloxy-propionic acid ethyl ester 
• 19201-34-4 1,1'-bis(1,1'-carboxyethyl) ether 
• 3677-70-1 1,1,2-triphenylprop-1-ene 
• 27816-36-0 2-Chloropropionamide 
• 922-52-1 (S)-2-((S)-1-Carboxy-ethyldisulfanyl)-propionic acid 
• 79-42-5 2-mercaptopropanoic acid 
• 31045-09-7 ethyl 2-methyl-1-oxaspiro[2,5]octane-2-carboxylate 
• 699-49-0 cis-1,2-Dimethyl-1,2-cyclopropanedicarboxylic acid 
• 699-49-0 (+/-)-1t,2c-Dimethyl-cyclopropan-1r,2t-dicarbonsaeure 

Relevant academic research and scientific papers

Preparation method of ethyl 2-chloropropionate

The invention discloses a preparation method of ethyl 2-chloropropionate. According to the preparation method, 2-chloropropionyl chloride and ethanol undergo an alcoholysis reaction at the molar ratioof 1: 1-3 at 5-20 DEG C under the anhydrous condition for 20-60 min, so as to prepare the ethyl 2-chloropropionate. The new process is conducted under the anhydrous condition. No sewage is generatedduring the process, and there is no environmental protection pressure.

Chloropyridylcarbonyl derivatives

Novel chloropyridylcarbonyl derivatives of the formula STR1 in which Het is STR2 n is 1 or 2, R1 is hydrogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C3-6 alkynyl, optionally substituted phenyl or optionally substituted pyrimidinyl, and R2 and R3, independently of each other, are hydrogen or C1-4 alkyl, and acid addition salts and metal salt complexes thereof, are outstandingly active as microbicides.

Structure-Activity Relationships in the Esterase-catalysed Hydrolysis and Transesterification of Esters and Lactones

The Broensted exponents for the alkaline hydrolysis of alkyl esters are 1.3 and 0.4 for substitution in the acyl and alcohol portions, respectively, which is indicative of a transition state which resembles the anionic tetrahedral intermediate with a localised negative charge.By contrast, the rate of the pig liver esterase (PLE)-catalysed hydrolysis shows little dependence upon the electron-withdrawing power of substituents.The values of kcat are independent of the pKa of the leaving group alcohol suggesting rate-limiting deacylation.There is a small steric effect of α-substitution in both the alcohol and carboxylic acid residues for the enzyme-catalysed reactions but the enzyme rate enhancement factor remains high for most esters.There is no substantial ee observed for the hydrolysis of racemic esters although the kinetic data can be used for determining the regioselective hydrolysis of diesters.Unsubstituted lactones are poor substrates for PLE but derivatives with hydrophobic substituents show kcat/Km values similar to those for acyclic esters.Dihydrocoumarin undergoes transesterification catalysed by PLE, kcat increases with increasing alcohol concentration indicative of rate-limiting deacylation.There is enantioselectivity in the PLE-catalysed hydrolysis of some racemic lactones but little or none in the transesterification of racemic alcohols with dihydrocoumarin.

Pentacarbonylmanganese enolate and dienolate complexes. Preparative and mechanistic considerations

Reactions of pentacarbonyl manganate anion with 4-halocrotonate esters or 2-halocarboxylate esters result in a complex set of inorganic and organic products, usually including the expected dienolate (or enolate) complexes.The reaction variables include the counterion, solvent, and halo group.The mechanism of the reaction has been investigated by conducting a thorough characterization of the reaction products under various conditions and also by carrying out model reactions.One can rationalize most of the non-organometallic products using either a radical or carbanion mechanism, but the latter seems to fit the available data better.Experimental procedures for optimizing the yield of the organometallic dienolate or enolate complexes have been worked out.

SYNTHESIS AND THERMAL PROPERTIES OF SIDE CHAIN TYPE LIQUID CRYSTALLINE POLYMERS WITH CHIRAL UNIT IN THE FLEXIBLE MOIETY

This paper is concerned with the synthesis and thermal properties for five families of side-chain type liquid crystalline polymers.All these side-chain type polymers showed an enantiotropic mesomorphic nature.A sharp reflexion was observed in the small angle region, whereas a broad halo or a relatively sharp peak was also detected in the wide angle region for all the polymers.The experimental values of the thickness of the smectic layer which can be easily assigned by the polarizing microscopic measurements were smaller than that of the calculated ones.This difference would be caused from the tilted arrangement in the smectic layer or smectic A like structure in which the side chain would be overlapped.

Resolution of racemic mixtures of aliphatic acid esters

Racemic mixtures of partially water-soluble esters defined by the formula STR1 wherein R and R1 represent hydrogen and C1 -C4 alkyl; R2 represents C1 -C4 alkyl and X represents halogen, aliphatic or aromatic groups and substituted derivatives thereof wherein R, R1 and X are different can be resolved by reducing the water solubility of a racemic mixture of said esters by means other than changing the chemical composition of the ester, contacting the racemic mixture of esters of reduced water solubility with a lipase enzyme from Candida cylindracea capable of stereospecifically resolving the racemic mixture of hydrolysis and stereospecifically resolving the racemic mixture.

Process for the preparation of an alkyl 2-chloropropionate by chlorinating an alkyl lactate

A racemic or optically active alkyl 2-chloropropionate is prepared, respectively, from a racemic or optically active alkyl lactate by, in a first step, gradually bringing the alkyl lactate into contact with the thionyl chloride, in the presence of an organic base, while maintaining, in the reaction mixture, an excess of thionyl chloride, relative to the amount of alkyl lactate introduced into this mixture, at a temperature below the decomposition point of the chlorosulphinate of the alkyl lactate, which is formed as an intermediate, and then, in a second step, in heating the reaction mixture resulting from the first step at a temperature which is at least equal to the decomposition point of the chlorosulphinate of the alkyl lactate. The alkyl 2-chloropropionates can be used for the manufacture of the racemic or optically active 2-phenoxypropionic acids.