622-25-3

Usage

Uses

Used in Chemical Industry:
BETA-CHLOROSTYRENE is used as a monomer for the production of various polymers and resins. Its unique structure allows for the creation of materials with specific properties, such as increased strength or resistance to certain conditions.
Used in Plastics Production:
BETA-CHLOROSTYRENE is used as a building block for the synthesis of plastics, contributing to the development of new materials with tailored characteristics for specific applications.
Used in Pharmaceutical Industry:
Although BETA-CHLOROSTYRENE is toxic and a potential carcinogen, it may be used as an intermediate in the synthesis of certain pharmaceutical compounds, where its reactivity and structural features are exploited to create desired drug molecules.
Used in Research and Development:
BETA-CHLOROSTYRENE serves as a valuable compound in academic and industrial research settings, where its properties and reactivity are studied to develop new applications and understand its behavior in various chemical reactions.

InChI:InChI=1/C8H7Cl/c9-7-6-8-4-2-1-3-5-8/h1-7H/b7-6-

Upstream product

• 100-42-5 styrene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 35115-76-5 2,3-dichloro-3-phenyl-propionic acid 
• 90649-87-9 2-chloro-3-hydroxy-3-phenyl-propionic acid 
• 621-82-9 Cinnamic acid 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 156-59-2 cis-1,2-Dichloroethylene 
• 29626-90-2 1-chloro-2-phenylethyl phenyl sulfoxide 
• 100-69-6 2-vinylpyridine 
• 88211-05-6 3-benzyl-3-chloro-3H-diazirine 
• 593-78-2 methyl hypochlorite 
• 67-56-1 methanol 
• 1074-11-9 1-(1,2-dichloroethyl)benzene 
• 88211-07-8 Benzylchlorocarbene 

Downstream Products

• 7087-31-2 trans-5-chloro-4-phenyl-[1,3]dioxane 
• 7087-31-2 cis-5-chloro-4-phenyl-[1,3]dioxane 
• 536-74-3 phenylacetylene 
• 1522-13-0 1,1,3-triphenylprop-2-yn-1-ol 
• 6111-82-6 1-phenylhex-1-ene 
• 65-85-0 benzoic acid 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 705-55-5 (E)-2-chloro-3-phenylacrylic acid 
• 43008-81-7 1-methyl-4-(3-phenylpropyl)benzene 
• 134539-87-0 1-methyl-4-(3-phenyl-1-propen-1-yl)benzene 
• 134539-86-9 1-methyl-4-(3-phenyl-2-propen-1-yl)benzene 
• 113791-93-8 cis-1-phenyl-2-(1-naphthylthio)ethene 
• 113791-94-9 trans-1-phenyl-2-(1-naphthylthio)ethene 
• 100-42-5 styrene 

Relevant academic research and scientific papers

Absolute Rate Constant for the Reaction of Benzylchlorocarbene with Hydrogen Chloride

The rate constant for the reaction of benzylchlorocarbene with HCL is 4.7E9 dm3 mol-1 s-1.

Generation and study of benzylchlorocarbene from a phenanthrene precursor

The curved plots of (carbene adduct)/(carbene-rearrangement product) versus carbene trapping agent, tetramethylene [TME], reported with benzylchlorodiazirine 1 have been reproduced. However, with the use of a non- nitrogenous precursor, plots of this type are approximately linear over the range of [TME] employed. Thus, any complex formed between benzylchlorocarbene and TME must collapse to form cyclopropane faster then it can fragment with rearrangement to β-chlorostyrene and TME. Diazirine 1 does photoisomerize to diazo compound 7, but this process is inefficient (φ = 0.075) and is not likely to be responsible for the curvature in plots of adduct/styrene versus [TME] observed with the diazirine precursor. Thus, the second, noncarbene, pathway to β-chlorostyrene is neither a carbene-olefin complex nor a diazo intermediate. It is proposed that the second pathway involves a rearrangement in the excited state of the diazirine, although other explanations cannot be discarded.

Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach

While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.

A Chlorinating Reagent Yields Vinyl Chlorides with High Regioselectivity under Heterogeneous Gold Catalysis

A novel chlorinating reagent with a high concentration of HCl has enabled the highly regioselective hydrochlorination of unactivated alkynes using a commercial nanogold catalyst. No overchlorination or hydration products were formed, and various functional groups were tolerated. This hydrochlorination method could be conducted under open air.

Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates

The individual molecules of α-chloroalkenyl boronates include both an electrophilic C?Cl bond and a nucleophilic C?B bond, which makes them intriguing organic synthons. Reported herein is a stereodivergent synthesis of both E and Z α-chloroalkenyl N-methyliminodiacetyl (MIDA) boronates through the direct chlorination of alkenyl MIDA boronates using tBuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the use of sp3-B MIDA boronate is the key contributor to the reactivity. The synthetic value of the boronate products was also demonstrated.

Pd(OAc)2/S=PPh3 accelerated activation of gem-dichloroalkenes for the construction of 3-arylchromones

The Pd-catalyzed regioselective intramolecular nucleophilic substitution of gem-dichloroalkene derivatives with salicylaldehydes leading to the synthesis of 3-arylchromones has been developed. Pd(OAc)2/S=PPh3 could activate gem-dichloroalkenes and undergo nucleophilic substitution by salicylaldehydes with the aid of a base.

Kinetics and mechanism of styrene epoxidation by chlorite: Role of chlorine dioxide

An investigation of the kinetics and mechanism for epoxidation of styrene and para-substituted styrenes by chlorite at 25 °C in the pH range of 5-6 is described. The proposed mechanism in water and water/acetonitrile includes seven oxidation states of chlorine (-I, 0, I, II, III, IV, and V) to account for the observed kinetics and product distributions. The model provides an unusually detailed quantitative mechanism for the complex reactions that occur in mixtures of chlorine species and organic substrates, particularly when the strong oxidant chlorite is employed. Kinetic control of the reaction is achieved by the addition of chlorine dioxide to the reaction mixture, thereby eliminating a substantial induction period observed when chlorite is used alone. The epoxidation agent is identified as chlorine dioxide, which is continually formed by the reaction of chlorite with hypochlorous acid that results from ClO produced by the epoxidation reaction. The overall stoichiometry is the result of two competing chain reactions in which the reactive intermediate ClO reacts with either chlorine dioxide or chlorite ion to produce hypochlorous acid and chlorate or chloride, respectively. At high chlorite ion concentrations, HOCl is rapidly eliminated by reaction with chlorite, minimizing side reactions between HOCl and Cl2 with the starting material. Epoxide selectivity (>90% under optimal conditions) is accurately predicted by the kinetic model. The model rate constant for direct reaction of styrene with ClO2(aq) to produce epoxide is (1.16 ± 0.07) × 10-2 M -1 s-1 for 60:40 water/acetonitrile with 0.20 M acetate buffer. Rate constants for para substituted styrenes (R = -SO3 -, -OMe, -Me, -Cl, -H, and -NO2) with ClO2 were determined. The results support the radical addition/elimination mechanism originally proposed by Kolar and Lindgren to account for the formation of styrene oxide in the reaction of styrene with chlorine dioxide.

Pyridine-assisted chlorinations and oxidations by palladium(IV)

The reactivity of the bis-NHC complex LPdIVCl4 (L = κ2-[R-NHCCH2NHC-R] with R = C14H 29) in chlorinations and oxidations of organic substrates was considerably increased in the presence of pyridine. For alkene chlorinations, this effect was due to the in situ formation of highly reactive LPd IVCl3(py)+, which was able to transfer Cl + to the C=C bond in a ligand-mediated process (devoid of π complexation), which did not require py dissociation. The enhanced reactivity in the presence of pyridine also extended to the oxidation of secondary and benzylic alcohols under mild conditions in a reaction where py served as a base, broadening the known scope of reactivity for PdIV complexes. LPdIVCl3(py)+ could be formed from Cl -/py exchange or from the oxidation of LPdIICl(py) + by Cl2. Taking advantage of the enhanced reactivities that pyridine coordination imparted on both PdII and PdIV complexes allowed for the catalytic chlorination of styrene with LPd IVCl4 as a sacrificial oxidant, thereby establishing the principal feasibility of PdII/PdIV catalyses that obviates PdII activations of the substrate.

Decarboxylative bromination of cinnamic acids by 2-iodoxybenzoic acid with tetrabutylammonium bromide

The decarboxylative bromination of cinnamic acids using the hypervalent iodine reagent 2-iodoxybenzoic acid with tetrabutylammonium bromide is described, providing good to excellent yields of bromostyrenes. Bromostyrenes are useful coupling components in a wide range of transition metal-catalysed coupling reactions.

Halofluorination of alkenes using trihaloisocyanuric acids and HF-pyridine

Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF-pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%. Georg Thieme Verlag Stuttgart · New York.