2039-87-4

Basic information

• Product Name: 2-Chlorostyrene
• Synonyms: (2-chlorophenyl)ethylene;1-chloro-2-ethenylbenzene;1-Chloro-2-vinylbenzene;2-chloro-styren;Benzene, 1-chloro-2-ethenyl-;benzene,1-chloro-2-ethenyl-;o-chloro-stryen;o-chloro-styren
• CAS NO: 2039-87-4
• Molecular Formula: C₈H₇Cl
• Molecular Weight: 138.59
• EINECS: 218-026-8
• Product Categories: Styrenes;High Refractive Index MonomersPolymer Science;Monomers;Photonic and Optical Materials;Styrene and Functionalized Styrene Monomers;Waveguide Materials
• Mol File: 2039-87-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: -63.1 °C
• Boiling Point: 58-60 °C7 mm Hg(lit.)
• Flash Point: 138 °F
• Appearance: clear colourless to light yellow liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.565(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble in water.
• BRN: 2038863
• CAS DataBase Reference: 2-Chlorostyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorostyrene(2039-87-4)
• EPA Substance Registry System: 2-Chlorostyrene(2039-87-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 45-20/22-36/37/38
• Safety Statements: 53-23-36/37/39-45-37/39-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: WL4160000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2039-87-4(Hazardous Substances Data)

Usage

Description

2-Chlorostyrene, also known as o-Chlorostyrene, is a clear colorless to light yellow liquid with flammable properties. It is an important raw material and intermediate used in various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuff.

Uses

Used in Organic Synthesis:
2-Chlorostyrene is used as a key intermediate for the production of specialty polymers and other chemical compounds. Its unique chemical structure allows for versatile reactions and modifications, making it a valuable component in the synthesis of various organic molecules.
Used in Pharmaceutical Industry:
2-Chlorostyrene is used as a building block in the development of new pharmaceuticals. Its reactivity and compatibility with other molecules make it suitable for creating novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Chlorostyrene is utilized as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides. Its properties enable the creation of effective and targeted compounds for agricultural use.
Used in Dyestuff Industry:
2-Chlorostyrene is employed in the production of dyes and pigments due to its ability to undergo specific chemical reactions that result in the formation of colored compounds. These dyes and pigments find applications in various industries, such as textiles, plastics, and printing.
Overall, 2-Chlorostyrene is a versatile and valuable compound with a wide range of applications across different industries, making it an essential component in the development of new products and technologies.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

2-Chlorostyrene may be sensitive to heat or prolonged exposure to light. 2-Chlorostyrene may polymerize.

Hazard

Central nervous system impairment and peripheral neuropathy.

Health Hazard

By analogy to styrene, ochlorostyrene is expected to cause central nervous system depression at extremely high concentrations and possibly irritation of the eyes, nose, and mucous membranes. There are no reports of adverse effects in humans.

Fire Hazard

2-Chlorostyrene is combustible.

Safety Profile

A skin and eye irritant. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC .

Potential Exposure

In organic synthesis; in the preparation of specialty polymers.

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Incompatibilities

Contact with elevated temperatures, strong oxidizers, strong bases; or acids may cause fire or explosion. May form peroxides; explosive polymerization may occur.

InChI:InChI=1/C8H7Cl/c1-2-7-5-3-4-6-8(7)9/h2-6H,1H2

Upstream product

• 704-96-1 trans-2-chlorocinnamic acid 
• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 108-24-7 acetic anhydride 
• 89-98-5 2-chloro-benzaldehyde 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 612-12-4 o-Xylylene dichloride 
• 60973-59-3 α,α-dichloro-o-xylene 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 80561-33-7 1--1,2-dihydropyridine 
• 19819-95-5 2-(2-chlorophenyl)-1-ethanol 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 

Downstream Products

• 159298-85-8 2-(2-chlorophenyl)-1-(morpholin-4-yl)ethanethione 
• 15851-90-8 2-Chlor-zimtsaeureamid 
• 83716-63-6 (+/-)-4-(2-chlorophenyl)-2-azetidinone 
• 113614-52-1 cis-5-(2-chlorophenyl)-3-(4-chlorophenyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine 
• 142742-42-5 (2R,3S)-cis-6-chloro-3-dimethyl(1,1,2-trimethylpropyl)siloxy-1-vinylcyclohexa-4,6-diene-2-ol 
• 128545-40-4 C₁₆H₁₁ClO₃S 
• 78388-29-1 2-methyl-4-trans-(2'-chloro)styrylisocarbostyryl 
• 78601-69-1 {2-[(Z)-2-(2-Chloro-phenyl)-vinyl]-4,5-dimethoxy-benzyl}-dimethyl-amine 
• 78601-69-1 {2-[(E)-2-(2-Chloro-phenyl)-vinyl]-4,5-dimethoxy-benzyl}-dimethyl-amine 
• 13524-04-4 (S)-1-(2'-chlorophenyl)ethanol 
• 13524-04-4 (R)-1-(o-chlorophenyl)ethanol 
• 7147-44-6 1-(2-chlorophenyl)ethanone oxime 
• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 62717-50-4 (R)-(-)-2-(2-chlorophenyl)oxirane 

Relevant articles and documents

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

In-situ facile synthesis novel N-doped thin graphene layer encapsulated Pd@N/C catalyst for semi-hydrogenation of alkynes

Transition metal-catalyzed semi-hydrogenation of alkynes has become one of the most popular methods for alkene synthesis. Specifically, the noble metal Pd, Rh, and Ru-based heterogeneous catalysts have been widely studied and utilized in both academia and industry. But the supported noble metal catalysts are generally suffering from leaching or aggregation during harsh reaction conditions, which resulting low catalytic reactivity and stability. Herein, we reported the facile synthesis of nitrogen doped graphene encapsulated Pd catalyst and its application in the chemo-selective semi-hydrogenation of alkynes. The graphene layer served as “bulletproof” over the active Pd Nano metal species, which was confirmed by X-ray and TEM analysis, enhanced the catalytic stability during the reaction conditions. The optimized prepared Pd@N/C catalyst showed excellent efficiency in semi-hydrogenation of phenylacetylene and other types of alkynes with un-functionalized or functionalized substituents, including the hydrogenation sensitive functional groups (NO2, ester, and halogen).