1712-71-6

Usage

Uses

Used in Fragrance and Flavor Industry:
1-chloro-3-isopropenylbenzene is used as a precursor for the production of cinnamyl alcohol, which is a key ingredient in the fragrance and flavor industries. Its conversion to cinnamyl alcohol is crucial for creating scents and tastes that are reminiscent of cinnamon, a widely used spice.
Used in Dye and Perfume Manufacturing:
In the dye and perfume industries, 1-chloro-3-isopropenylbenzene is utilized as a starting material for the synthesis of various dyes and perfumes. Its chemical properties allow for the creation of a range of aromatic compounds that contribute to the color and scent profiles of these products.
Used in Organic Chemistry as a Versatile Intermediate:
1-chloro-3-isopropenylbenzene is used as a versatile intermediate in organic chemistry for the synthesis of pharmaceuticals, agrochemicals, and polymers. Its reactivity and functional group compatibility make it a valuable component in the development of new chemical entities and materials.
Used in Chemical Synthesis:
1-chloro-3-isopropenylbenzene is used as a reactant in various chemical synthesis processes. Its ability to participate in addition, substitution, and other types of chemical reactions makes it a useful building block for creating complex organic molecules.
Safety Considerations:
It is important to handle 1-chloro-3-isopropenylbenzene with care due to its potential hazards and irritant properties. Proper safety measures should be taken to minimize exposure and ensure the well-being of those working with 1-chloro-3-isopropenylbenzene.

InChI:InChI=1/C9H9Cl/c1-7(2)8-4-3-5-9(10)6-8/h3-6H,1H2,2H3

Upstream product

• 7073-93-0 m-chlorocumene 
• 31002-87-6 2-(3-chlorophenyl)propan-2-ol 
• 108-24-7 acetic anhydride 
• 75-24-1 trimethylaluminum 
• 535-80-8 3-chlorobenzoate 
• 1605-72-7 dichlorocarbene 
• 2175-91-9 6,6'-dimethyl fulvene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 99-02-5 3'-Chloroacetophenone 
• 108-37-2 1-bromo-3-chlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 2905-65-9 methyl 3-chlorobenzoate 

Downstream Products

• 7073-93-0 m-chlorocumene 
• 77826-65-4 C₉H₁₀Cl⁽¹⁺⁾ 
• 98-83-9 isopropenylbenzene 
• 31002-87-6 2-(3-chlorophenyl)propan-2-ol 
• 40473-10-7 2-chloro-2-(3'-chlorophenyl)propane 
• 56077-92-0 peroxymethylene radical 
• 99-02-5 3'-Chloroacetophenone 
• 18027-96-8 m-i-propyl(trimethylsilyl)benzene 
• 17911-24-9 triethyl-(3-isopropyl-phenyl)-silane 
• 947383-49-5 (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene 
• 193531-42-9 1-(3-bromoprop-1-en-2-yl)-3-chlorobenzene 
• 1253286-08-6 (S)-ethyl 4-(3-chlorophenyl)-2-hydroxy-2-(trifluoromethyl)pent-4-enoate 
• 1450884-59-9 (S)-methyl 4-(3-chlorophenyl)-2-hydroxy-2-(trifluoromethyl)-pent-4-enoate 

Relevant academic research and scientific papers

Synthesis of 3-Benzazepines by Metal-Free Oxidative C–H Bond Functionalization–Ring Expansion Tandem Reaction

A metal-free synthesis of biologically important benzazepines is achieved through a single synthetic operation involving an oxidative C–H bond functionalization and ring expansion with diazomethanes as key reagent. This represents a new, strong methodology for the straightforward construction of the seven-ring N-heterocyclic structures under mild conditions using a 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) oxoammonium salt as oxidant. Moderate to good yields are achieved from simple, readily available tetrahydroisoquinolines, and this methodology has been further successfully applied for the synthesis of the 3-benzazepine drug Lorcaserin. A possible mechanistic pathway for the ring expansion step, comprising the extrusion of nitrogen in a concerted asynchronic process, is proposed based on both mechanistic proof and density function theory (DFT) calculations. (Figure presented.).

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.

Aqueous ZnCl2 Complex Catalyzed Prins Reaction of Silyl Glyoxylates: Access to Functionalized Tertiary α-Silyl Alcohols

An efficient Prins reaction of silyl glyoxylates in the presence of an aqueous ZnCl2 complex as a catalyst was developed, providing functionalized tertiary α-silyl alcohols in high yields under mild conditions. A preliminary investigation indicated that the aqueous ZnCl2 complex acted as a dual functional catalyst of Br?nsted and Lewis acid to activate the carbonyl groups of silyl glyoxylates via a dual-activation model.

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

Synthesis of N-Alkylpyridin-4-ones and Thiazolo[3,2- a]pyridin-5-ones through Pummerer-Type Reactions

N-Alkylated 4-pyridones were obtained through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride-activated sulfoxides and 4-fluoropyridine derivatives, followed by hydrolysis. On the other hand, triflic anhydride-activated benzyl 6-fluoro-2-pyridyl sulfoxide could react with alkenes or alkynes to afford thiazolo[3,2-a]pyridin-5-ones, via the pyridinium salt intermediates.

Chiral Br?nsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes

The first highly efficient and practical chiral Br?nsted acid catalyzed dynamic kinetic asymmetric hydroamination (DyKAH) of racemic allenes and asymmetric hydroamination of unactivated dienes with both high E/Z selectivity and enantioselectivity are described herein. The transformation proceeds through a new catalytic asymmetric model involving a highly reactive π-allylic carbocationic intermediate, generated from racemic allenes or dienes through a proton transfer mediated by an activating/directing thiourea group. This method affords expedient access to structurally diverse enantioenriched, potentially bioactive alkenyl-containing aza-heterocycles and bicyclic aza-heterocycles.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides

The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.