17639-93-9

Basic information

• Product Name: Methyl 2-chloropropionate
• Synonyms: 2-chloro-propanoicacimethylester;2-chloro-propionicacimethylester;alpha-Chloropropionic acid methyl ester;CH3CHClC(O)OCH3;Methyl alpha-chloropropionate;Propanoic acid, 2-chloro-, methyl ester;Propionic acid, 2-chloro-, methyl ester;2-CHLOROPROPIONIC ACID METHYL ESTER
• CAS NO: 17639-93-9
• Molecular Formula: C₄H₇ClO₂
• Molecular Weight: 122.55
• EINECS: 241-624-5
• Product Categories: API Intermediate
• Mol File: 17639-93-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: -10 °C
• Boiling Point: 132-133 °C(lit.)
• Flash Point: 101 °F
• Appearance: clear colorless liquid
• Density: 1.075 g/mL at 25 °C(lit.)
• Vapor Density: 4.22 (vs air)
• Vapor Pressure: 5.25 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: 2.8-13.9%(V)
• Water Solubility: immiscible
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
• BRN: 1421535
• CAS DataBase Reference: Methyl 2-chloropropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-chloropropionate(17639-93-9)
• EPA Substance Registry System: Methyl 2-chloropropionate(17639-93-9)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16
• RIDADR: UN 2933 3/PG 3
• WGK Germany: 1
• RTECS: UE9100000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17639-93-9(Hazardous Substances Data)

Usage

Description

Methyl 2-chloropropionate is a colorless liquid with a flash point of 101°F and a density of 8.9 lb/gal. It is insoluble in water and can be irritating and narcotic in high concentrations. This chemical is primarily used as a solvent and in the production of other chemicals and dyes.

Uses

1. Used in Polymer Synthesis:
Methyl 2-chloropropionate is used as an initiator in the synthesis of acrylamide homopolymers and acrylamide-N-isopropylacrylamide block copolymers. It plays a crucial role in the polymerization process, enabling the formation of these polymers with specific properties and applications.
2. Used in Pharmaceutical Industry:
Methyl 2-chloropropionate is used to produce 2-thiophen-2-yl-propionic acid methyl ester, which is an important intermediate in the synthesis of various pharmaceutical compounds. This application highlights its significance in the development of new drugs and therapeutic agents.
3. Used in Chemical and Dye Production:
As a solvent, Methyl 2-chloropropionate is utilized in the production of other chemicals and dyes. Its solvent properties make it a valuable component in various chemical reactions and processes, contributing to the synthesis of a wide range of products.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

METHYL CHLOROPROPIONATE is a halogenated ester. Reacts 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. Reacts exothermically with bases. Flammable hydrogen is generated 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.

Safety Profile

Poison by intraperitoneal route. See also ESTERS. A flammable liquid when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-.

InChI:InChI=1/C4H7ClO2/c1-7-4(6)2-3-5/h2-3H2,1H3

Upstream product

• 75-44-5 phosgene 
• 547-64-8 methyl lactate 
• 121769-68-4 [9,9']Biphenanthrenyl-10,10'-diol; compound with 2-chloro-propionic acid methyl ester 
• 121769-68-4 [9,9']Biphenanthrenyl-10,10'-diol; compound with 2-chloro-propionic acid methyl ester 
• 5445-17-0 Methyl 2-bromopropionate 
• 67-56-1 methanol 
• 554-12-1 propanoic acid methyl ester 
• 108365-84-0 2-Chloro-2-dimethoxymethyl-3-methyl-oxirane 
• 7623-09-8 2-chloropropionyl chloride 
• 87894-32-4 2-chloropropionaldehyde dimethyl acetal 
• 7013-11-8 2,3-dichlorobut-1-ene 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 

Downstream Products

• 547-64-8 methyl lactate 
• 107-31-3 Methyl formate 
• 78-89-7 2-chloro-1-propanol 
• 111870-36-1 C₁₀H₉ClN₃O₈^(1-)*Na⁽¹⁺⁾ 
• 150535-91-4 2-(4-Phenyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid methyl ester 
• 75386-98-0 2-o-Tolylamino-propionic acid methyl ester 
• 7028-57-1 2-methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine 
• 901450-96-2 2-(4-Acetylamino-phenoxy)-propionic acid methyl ester 
• 52888-49-0 methyl N-(2,6-dimethylphenyl)alaninate 
• 1254714-55-0 C₁₈H₁₈N₂O₂ 
• 1254714-66-3 C₁₈H₁₈N₂O₂ 
• 1254714-79-8 C₁₈H₁₈N₂O₂ 
• 77959-48-9 4-(1-methoxycarbonyl-ethyl)-benzoic acid methyl ester 
• 79443-97-3 methyl 2-(4-methylphenyl)propanoate 

Relevant articles and documents

Mass Spectra of Halogenated Esters. 7. Methyl Esters of 2-Chloro C2-C20 n-Alkanoic Acids

The mass spectral fragmentation of a homologous series of methyl esters of 2-chloro n-alkanoic acids ranging from acetic (C2) to eicosanoic (C20) acid on electron impact has been investigated.The fragmentation pathways were elucidated with the aid of the first field-free region metastable ions, the results being presented with one compound, i.e. with ionized methyl 2-chloro-octanoate.Owing to the Cl/H exchanges and to the formation of the nonchlorinated parent esters prior to the fragmentations the spectra show the peak pairs with and without the chlorine atom.The effects become more evident with increasing chain length; shown most visually by the abundance ratios of the McLafferty rearrangement ions at m/z 108/110 and 74, and fragments at m/z 121/123 and 87.

Mechanism of halogen exchange in ATRP

Detailed mechanistic studies reveal that halogen exchange (HE) in ATRP can occur not only by a radical pathway (atom transfer) but also by an ionic pathway (SN2 reaction) because Cu(I)(L)X and Cu (II)(L)X2 complexes contain weakly associated halide anion that can participate in the SN2 reaction with alkyl halide (ATRP initiator). Both pathways were kinetically studied, and their contributions to the HE process were quantitatively evaluated for seven alkyl halides and three Cu(I)(L)Cl complexes. Radical pathway dominates the HE process for 3° and 2° alkyl bromides with more active complexes such as Cu (I)(TPMA)Cl. Interestingly, ionic pathway dominates for 1° alkyl bromides and less active ATRP catalysts. These studies also revealed that degree of association of alkyl halide anion depends on the structure of copper complexes. In addition, radical pathway is accompanied by the reverse reactions such as deactivation of radicals to alkyl bromides and also activation of alkyl chlorides, reducing the efficiency of halogen exchange.

Preparation of a mannich base intermediate for 2-[(4-heterocyclic-phenoxymethyl)-phenoxy]-alkanoates

A Mannich base intermediate for 2-[(4-heterocyclic-phenoxymethyl)-phenoxyl]-alkanoates and methods for its preparation are provided. A method for preparation of an alkyl 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate comprises the steps of: reacting a mixture of m-alkyl phenol, a secondary amine, and an aldehyde, with or without a catalyst, in a first solvent at reflux temperatures to form a 2-[(secondary amino)methyl]-5-alkylphenol. That product is then reacted with an alkyl 2-haloalkanoate, and an alkali metal carbonate, with or without a second catalyst in a second solvent at reflux temperatures to form the 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate. The aldehyde may be paraformaldehyde, aqueous formaldehyde, formaldehyde, or polymerized acetal derivatives thereof. The first solvent may be acetonitrile or toluene. The catalyst may be an acid catalyst or a base catalyst. In the preferred embodiment the Mannich base is a 2-[(secondary amino)-methyl]-5-alkylphenol, or a 2-[2-(secondary amino methyl)-5-alkylphenoxy]-alkanoate.