1074-11-9

Basic information

• Product Name: (1,2-dichloroethyl)benzene
• Synonyms: Styrenedichloride;(1 2-DICHLOROETHYL)BENZENE PRACTICAL GRADE;1-(1,2-Dichloroethyl)benzene;1,2-Dichloro-1-phenylethane;Benzene, (1,2-dichloroethyl)-
• CAS NO: 1074-11-9
• Molecular Formula: C₈H₈Cl₂
• Molecular Weight: 175.05512
• EINECS: 214-035-6
• Mol File: 1074-11-9.mol

Chemical Properties

• Melting Point: 44.47°C (estimate)
• Boiling Point: 228.7°C (estimate)
• Flash Point: 106°C
• Appearance: /
• Density: 1.2400
• Vapor Pressure: 0.0757mmHg at 25°C
• Refractive Index: 1.5544
• CAS DataBase Reference: (1,2-dichloroethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (1,2-dichloroethyl)benzene(1074-11-9)
• EPA Substance Registry System: (1,2-dichloroethyl)benzene(1074-11-9)

Safety Data

• Hazardous Substances Data: 1074-11-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(1,2-dichloroethyl)benzene is used as a precursor in the production of various organic compounds, contributing to the synthesis of a range of chemical products due to its reactive nature.
Used as a Solvent:
In industrial applications, (1,2-dichloroethyl)benzene is employed as a solvent for specific processes, taking advantage of its ability to dissolve certain substances effectively.
Used in Pharmaceutical Industry:
(1,2-dichloroethyl)benzene is used as a chemical intermediate in the pharmaceutical industry for the synthesis of various drugs, given its reactivity and compatibility with other chemical entities.
Used in Chemical Research:
In the field of chemical research, (1,2-dichloroethyl)benzene is utilized as a model compound to study chemical reactions and mechanisms, providing insights into the behavior of similar compounds.

InChI:InChI=1/C8H8Cl2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 67-56-1 methanol 
• 63603-28-1 1-methoxy-1-phenyl-2-phenylselenoethane 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 7719-12-2 phosphorus trichloride 
• 14989-30-1 hypochloric acid 
• 7726-95-6 bromine 
• 67-63-0 isopropyl alcohol 
• 64-17-5 ethanol 
• 96-09-3 styrene oxide 
• 71-23-8 propan-1-ol 
• 78-92-2 iso-butanol 

Downstream Products

• 618-34-8 1-chlorostyrene 
• 622-25-3 1-(2-chlorovinyl)benzene 
• 95-15-8 Benzo[b]thiophene 
• 100-42-5 styrene 
• 1261238-97-4 2-(2-chloro-1-phenylethyl)thiophene 
• 3583-85-5 (+/-)-1,2-bis(diphenylphosphino)phenylethane P,P'-dioxide 
• 1229530-95-3 C₁₆H₂₈O₂P₂ 
• 1229530-97-5 C₄₀H₇₆O₂P₂ 
• 96-09-3 styrene oxide 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Copper-catalyzed regioselective chloroamination of alkenes with chlorotrimethylsilane and n-fluorobenzenesulfonimide under microwave-assisted conditions

A copper-catalyzed chloroamination of alkenes with chlorotrimethylsilane and N-fluorobenzenesulfonimide has been developed. The reactions were complete within 1 h at 120 °C by means of microwave heating. The present chloroamination proceeds with a perfect regioselectivity and is compatible with various functional groups. The preliminary mechanistic investigation revealed that the reaction involves a radical process. The utility of the present method was demonstrated by scalable, operationally simple and safe system.

A Direct S0→Tn Transition in the Photoreaction of Heavy-Atom-Containing Molecules

According to the Grotthuss–Draper law, light must be absorbed by a substrate to initiate a photoreaction. There have been several reports, however, on the promotion of photoreactions using hypervalent iodine during irradiation with light from a non-absorbing region. This contradiction gave rise to a mystery regarding photoreactions involving hypervalent iodine. We demonstrated that the photoactivation of hypervalent iodine with light from the apparently non-absorbing region proceeds via a direct S0→Tn transition, which has been considered a forbidden process. Spectroscopic, computational, and synthetic experimental results support this conclusion. Moreover, the photoactivation mode could be extended to monovalent iodine and bromine, as well as bismuth(III)-containing molecules, providing new possibilities for studying photoreactions that involve heavy-atom-containing molecules.

STRUCTURE OF POLYMERS ON THE BASIS OF CHLORINATED STYRENE AND SODIUM DISULPHIDE

A polycondensation of a mixture of halogen derivatives of styrene obtained at direct chlorination of styrene and containing ca. 80 percent α,β-dichloroethylbenzene and sodium disulphide was studied.Polysulphide liquid low molecular polymers were obtained.By means of molecular spectroscopy, fractionation and the elemental analysis the structure of the synthesized products was studied.It was proved, that the essential unit is the styrenedisulphide one.The role of monofunctional monomer and of nonchlorinated styrene in reaction conditions was indicated

Convenient in situ generation of various dichlorinating agents from oxone and chloride: Diastereoselective dichlorination of allylic and homoallylic alcohol derivatives

A safe and convenient protocol was developed for in situ generation of various dichlorinating agents (cf. Cl2, NCl3, Et 4NCl3, ArICl2) from oxone and chloride. The synthetic utility of this protocol was demonstrated by diastereoselective dichlorination of a series of allylic and homoallylic alcohol derivatives with excellent yields and diastereoselectivity. The Royal Society of Chemistry 2013.

Quaternary ammonium polychlorides as efficient reagents for chlorination of unsaturated compounds

Chlorination of unsaturated compounds by benzyltributylammonium polychlorides results in higher yields of addition products compared to those obtained with molecular chlorine.

Reaction of Styrene with Chlorine Dioxide

Reaction of styrene with chlorine dioxide under various conditions selectively produces 1-phenyl- 2-chloroethanone, with 1-phenyl-2-chloroethanol, 2-hydroxy-1-phenylethanone, (1,2-dichloroethyl)benzene, (2-chloro-1-phenyl)ethene, and (1,2,2-trichloroethyl

Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride

The combination of diphenyl sulfoxide and oxalyl chloride was used to accomplish the dichlorination of olefins, in which chlorodiphenylsulfonium salt generated in situ was proposed to be the real active species as a chloronium ion source.

The Electrochemical cis-Chlorination of Alkenes

The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.

Flexible on-site halogenation paired with hydrogenation using halide electrolysis

Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.

TEMPO-Regulated Regio- and Stereoselective Cross-Dihalogenation with Dual Electrophilic X+ Reagents

A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+ reagents. Formally, the ICl, BrCl, I2 and Br2 were generated in-situ, which enabled high regio- or stereoselective access to a myriad of iodochlorination, bromochlorination and homo-dihalogenation products with a wide spectrum of functionalities. With its mild conditions and operational simplicity, this method could enable wide applications in organic synthesis, which was exemplified by divergent synthesis of two pharmaceuticals. Detailed mechanistic investigations via radical clock reaction, pinacol ring expansion and Hammett experiments were conducted, which confirmed the intermediacy of halonium ion. In addition, a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.