598-79-8

Basic information

• Product Name: 2-Chloroacrylic acid
• Synonyms: 2-Chloroprop-2-enoic acid;2-Chloro-2-propenoic acid;2-Chloropropenoic acid;2-chloro-2-propenoicaci;2-chloro-acrylicaci;2-Propenoic acid, 2-chloro-;Acrylic acid, 2-chloro-;chloroacrylicacid
• CAS NO: 598-79-8
• Molecular Formula: C₃H₃ClO₂
• Molecular Weight: 106.51
• EINECS: 209-953-9
• Product Categories: monomer
• Mol File: 598-79-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 65°C
• Boiling Point: 118.27°C (rough estimate)
• Flash Point: 73.1 °C
• Appearance: white crystallized powder
• Density: 1.2288 (rough estimate)
• Vapor Pressure: 0.163mmHg at 25°C
• Refractive Index: 1.4100 (estimate)
• PKA: 2.41±0.11(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1098503
• CAS DataBase Reference: 2-Chloroacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroacrylic acid(598-79-8)
• EPA Substance Registry System: 2-Chloroacrylic acid(598-79-8)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• RTECS: AS5952000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 598-79-8(Hazardous Substances Data)

Usage

Description

2-Chloroacrylic acid, also known as 2-chloropropenoic acid, is a chlorocarboxylic acid derived from acrylic acid with a hydrogen atom at position 2 substituted by chlorine. It is a halochemical and an important compound in organic synthesis, characterized by its unique chemical properties and reactivity.

Uses

Used in Halochemicals Industry:
2-Chloroacrylic acid is used as a key intermediate in the production of various halochemicals. Its unique structure allows for further chemical reactions and modifications, making it a valuable building block in the synthesis of a wide range of compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 2-chloroacrylic acid serves as a versatile reagent for the creation of various organic compounds. Its chlorine atom can be replaced by other functional groups, enabling the synthesis of a diverse array of molecules with different properties and applications.
Used in Pharmaceutical Industry:
2-Chloroacrylic acid can be utilized in the development of pharmaceutical compounds, particularly in the synthesis of drugs targeting specific biological pathways. Its unique chemical properties make it a promising candidate for the design of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloroacrylic acid can be employed in the synthesis of various pesticides and herbicides. Its reactivity and functional group compatibility allow for the development of effective compounds for crop protection and management.
Used in Material Science:
2-Chloroacrylic acid can also be used in the development of new materials with specific properties, such as polymers with tailored characteristics for various applications, including coatings, adhesives, and fibers. Its versatility in organic synthesis makes it a valuable component in the creation of advanced materials.

InChI:InChI=1/C3H3ClO2/c1-2(4)3(5)6/h1H2,(H,5,6)/p-1

Upstream product

• 50-00-0 formaldehyd 
• 79-01-6 Trichloroethylene 
• 565-64-0 2,3-dichloropropanoic acid 
• 683-51-2 2-chloro-2-propenal 
• 75-99-0 2,2-Dichloropropionic acid 
• 26438-89-1 2-chloro-3-fluoropropanoic acid 
• 138250-73-4 2-chloro-3-hydroxypropionic acid 
• 7664-93-9 sulfuric acid 
• 124-38-9 carbon dioxide 
• 105949-84-6 3-(1-chloroethenyl)-1,2,4-trioxolane 
• 67-56-1 methanol 
• 127-09-3 sodium acetate 
• 2601-89-0 2,3-dichloropropionitrile 
• 67280-54-0 3-bromo-2-chloro-propionic acid 

Downstream Products

• 80-63-7 methyl 2-chloroacrylate 
• 565-64-0 2,3-dichloropropanoic acid 
• 687-46-7 ethyl 2-chloroacrylate 
• 56236-43-2 1,2-bis-(2-chloro-acryloyloxy)-ethane 
• 29617-66-1 (S)-2-chloropropanoic acid 
• 4141-50-8 1,2-bis(diphenylphosphinoyl)ethane 
• 21369-76-6 α-chloroacryloyl chloride 
• 15366-34-4 methyl 1H-pyrazole 3-carboxylate 
• 715-12-8 (E)-3-(p-toluenesulfonyl)-acrylic acid 
• 1218782-02-5 (3S)-3-[((3-(N-benzyloxycarbonyl)amino-3-methoxycarbonyl)propyl(hydroxy)phosphinyl)]-2-chloropropanoic acid 

Relevant articles and documents

A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids

The homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α-halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide-, halogen- or proton- Mg exchange accounts for the wide scope of the reaction. (Figure presented.).

Reaction of 2,3-dihalopropionic acids and their derivatives with P- and N-nucleophiles

3-(Triphenylphosphoniochlorido)acrylic and 2,3-dichloropropionic acids react with triphenylphosphine to form 1,2-bis(triphenylphosphoniochlorido) ethane. Under analogous conditions, 2,3-dibromopropionic acid undergoes debromination followed by triphenylphosphine addition to give, after water treatment, 3-(triphenylphosphoniobromido)propionic acid. 2,3- Dihalopropionitriles react similarly, providing 3-(triphenylphosphoniohalido) propionitriles. The reaction of 2,3-dibromopropionamide with triphenylphosphine was performed to show that E-(triphenylphosphoniobromido)acrylic acid is capable, by contrast to what was reported previously, of reacting with triphenylphosphine. Pyridine forms with 2,3-dihalopropionic acids vinylpyridinium halides, while the reactions with aliphatic amines gives rise to dehydrohalogenation products.

Monoozonides of chloro-substituted conjugated dienes: preparation, stability, and some chemical reactions

The chlorodienes (E)-4-chloro-3-methyl-1,3-hexadiene (5a), (E) and (Z)-4-chloro-2,3-dimethyl-1,3-hexadiene (5b/6b), (E,E)-5-chloro-4-methyl-2,4-heptadiene (5c), (4E)- and (4Z)-5-chloro-3,4-dimethyl-2,4-heptadiene (5d/6d), chloroprene (11a), and 2-chloro-3-methyl-1,3-butadiene (11b) are selectively ozonized at the non-chlorinated double bonds to give the corresponding monoozonides 7, 8, and 12.Further ozonolyzis of the monoozonides of 5b and of 11b in methanol as well as epoxidation of the monoozonide of 5b and subsequent reaction of the resulting chloroepoxide with AgBF4 are described.