698-88-4

Basic information

• Product Name: DICHLOROSTYRENE
• Synonyms: DICHLOROSTYRENE;1,1-Dichloro-2-phenylethene;Benzene, (2,2-dichloroethenyl)-
• CAS NO: 698-88-4
• Molecular Formula: C₈H₆Cl₂
• Molecular Weight: 173.04
• Mol File: 698-88-4.mol

Chemical Properties

• Melting Point: 48.5°C (estimate)
• Boiling Point: 230.44°C (rough estimate)
• Appearance: /
• Density: 1.2531
• Refractive Index: 1.5852 (estimate)
• CAS DataBase Reference: DICHLOROSTYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLOROSTYRENE(698-88-4)
• EPA Substance Registry System: DICHLOROSTYRENE(698-88-4)

Safety Data

• Hazardous Substances Data: 698-88-4(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Plastics Industry:
DICHLOROSTYRENE is used as a monomer for the production of copolymers and resins, contributing to the development of various polymeric materials with enhanced properties.
Used in Chemical Synthesis:
DICHLOROSTYRENE is used as a chemical intermediate for synthesizing other compounds, playing a crucial role in the creation of new chemical entities for diverse applications.

Upstream product

• 67-66-3 chloroform 
• 100-52-7 benzaldehyde 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 71-43-2 benzene 
• 56-23-5 tetrachloromethane 
• 129715-34-0 trans-2,2-Dichloro-3-phenyl-1-(2,4,6-tri-t-butylphenyl)-1-phosphirane 
• 592-41-6 1-hexene 
• 3883-13-4 2,2,2-trichloroethylbenzene 
• 90-17-5 2,2,2-trichloro-1-phenylethyl acetate 
• 135603-21-3 2,2-diethyl-4-phenyl-2,3,3-trichloro-1,2λ⁵ oxaphosphetane 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 24768-49-8 (Dichlormethylen)sulfoxid 
• 908094-04-2 phenyldiazomethane 
• 45114-85-0 tris(dimethylamino)phosphonium cation 

Downstream Products

• 6626-84-2 dimethyl 2-benzylidenepropanedioate 
• 584-45-2 2-benzylidenemalonic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 140-10-3 cis-cinnamic acid 
• 948-98-1 (E)-α-chlorostilbene 
• 128080-47-7 cis-2-phenyl-1-tolyl-1-chloroethene 
• 948-99-2 α-chloro-(Z)-stilbene 
• 77341-89-0 2-butyl-1-phenyl-1-hexene 
• 58-72-0 Triphenylethylene 
• 1460-06-6 (1-chloroethene-1,2-diyl)dibenzene 
• 1483-82-5 phenylethynyl chloride 
• 536-74-3 phenylacetylene 
• 65-85-0 benzoic acid 
• 62-23-7 4-nitro-benzoic acid 

Relevant articles and documents

Copper(I)/Ligand-Catalyzed 5- endo Radical Cyclization-Aromatization of 2,2,2-Trichloroethyl Vinyl Ethers: Synthesis of 2,3-Difunctionalized 4-Chlorofurans

Copper(I)/ligand-catalyzed one pot synthesis of highly substituted 2,3-difunctionalized-4-chlorofurans has been reported. The reaction proceeds via a Cu(I)-catalyzed regioselective 5-endo-trig radical cyclization of 2,2,2-trichloroethyl vinyl ethers follo

Visible-Light-Mediated Z -Stereoselective Monoalkylation of β,β-Dichlorostyrenes by Photoredox/Nickel Dual Catalysis

Metal-catalyzed alkylation of 1,1-dihalovinyl moiety commonly suffers from both a lack of stereoselectivity and the overreaction leading to the dialkylation product. The methodology described herein features a new pathway to alkylate stereoselectively β,β-dichlorostyryl substrates to provide the Z -trisubstituted olefin only with fair to good yields. This cross-coupling reaction bears on the smooth and photoinduced formation of a C-centered radical that engages in a nickel-catalyzed organometallic cycle to form the key C sp2-C sp3bond.

Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures

The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

A Robust One-Step Approach to Ynamides

A robust one-step synthetic strategy for ynamide with cheap and easily available stock chemicals vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect to vinyl dichloride as well as electron-deficient amide were observed.

Method for producing fluorine-containing olefin

A method for producing at least one compound selected from the group consisting of a compound represented by formula (10), a compound represented by formula (11), a compound represented by formula (12), and a compound represented by formula (13), by reacting a compound represented by formula (2) and a compound represented by formula (7) in the presence of at least one compound selected from the group consisting of a compound represented by formula (1), a compound represented by formula (3), a compound represented by formula (4), a compound represented by formula (8), and a compound represented by formula (9).

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Pd0-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates

A novel and fully chemo- and stereoselective three component strategy leading to Z-α-chloroacrylates by a Pd0-catalyzed reaction of CO (1 atm) with 1,1-dichloro-1-alkenes and various alcohols is disclosed. This catalytic approach compares favourably with the Wittig type strategies as α-chloroacrylates of pure Z configuration are obtained in high yield. The Royal Society of Chemistry.

METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE

Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.

Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN

We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.