6268-36-6

Basic information

• Product Name: (2-chloroprop-2-en-1-yl)benzene
• Synonyms: Benzene, (2-chloroallyl)-
• CAS NO: 6268-36-6
• Molecular Formula: C₉H₉Cl
• Molecular Weight: 152.6208
• Mol File: 6268-36-6.mol

Chemical Properties

• Boiling Point: 205.6°C at 760 mmHg
• Flash Point: 73.6°C
• Density: 1.052g/cm³
• Vapor Pressure: 0.355mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: (2-chloroprop-2-en-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2-chloroprop-2-en-1-yl)benzene(6268-36-6)
• EPA Substance Registry System: (2-chloroprop-2-en-1-yl)benzene(6268-36-6)

Safety Data

• Hazardous Substances Data: 6268-36-6(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Production:
(2-chloroprop-2-en-1-yl)benzene is used as a monomer in the production of various polymers and resins. Its unique structure allows for the creation of polymers with specific properties, making it a valuable component in the manufacturing process.
Used in Pharmaceutical Synthesis:
(2-chloroprop-2-en-1-yl)benzene is used as an intermediate in the synthesis of pharmaceuticals. Its reactive chloromethyl group can be used to form new chemical bonds, enabling the production of a wide range of medicinal compounds.
Used in Agrochemical Synthesis:
(2-chloroprop-2-en-1-yl)benzene is also used in the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility as a chemical intermediate allows for the development of effective products for agricultural applications.
Safety Precautions:
It is important to handle (2-chloroprop-2-en-1-yl)benzene with care, as it can be harmful if inhaled or ingested, and it can cause irritation to the skin and eyes. Proper safety measures should be taken during its use and storage to minimize potential risks.

Upstream product

• 108-86-1 bromobenzene 
• 39557-31-8 3-iodo-2-chloropropene 
• 111860-73-2 C₁₅H₁₅Cl₃Se 
• 65523-62-8 1-(2-chloro-prop-2-ene-1-sulfonyl)-4-methyl-benzene 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 10147-11-2 propargyl benzene 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 300-57-2 allylbenzene 
• 100-56-1 phenylmercury(II) chloride 
• 103-79-7 1-phenyl-acetone 

Downstream Products

• 103-82-2 phenylacetic acid 
• 13099-50-8 2-methyl-1-phenyl-1-propene, β,β-dimethylstyrene 
• 172796-62-2 (C₅H₅)2Zr(Cl)(CCH₂CH₂C₆H₅) 
• 126300-47-8 2-benzyl-1,4-pentadiene 
• 13099-51-9 2,2-Dichlor-1-phenyl-propan 

Relevant articles and documents

Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis

Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.

Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides

An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido RuIV species as a key intermediate of the reaction.

Aryl radical formation by copper(I) photocatalyzed reduction of diaryliodonium salts: NMR Evidence for a CuII/CuI mechanism

Photocatalyzed reduction of diaryliodonium salts was achieved by using [Cu(dpp)2][PF6] as a photoactive complex and DIPEA as a reductive quench. The application of a copper catalyst allows the generation of aryl radicals under mild conditions and maintains their reactivity for C-C bond formation processes.

First cross-coupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oxime-derived palladacycle

(Chemical Equation Presented) Potassium aryltrifluoroborates are cross-coupled with aryl and heteroaryl chlorides using a 4-hydroxyacetophenone oxime-derived palladacycle as precatalyst, K2CO3 as base, and TBAB as additive in refluxing water under conventional and microwave heating affording the corresponding biphenyls under phosphine-free conditions. For the arylation of allyl and benzyl chlorides, KOH is used as base in acetone-water (3:2) at rt or 50 °C using 0.1 mol % Pd loading providing allylbenzenes and diarylmethanes, respectively.

COUPLING OF ARYL GRIGNARD REAGENTS BY ELECTRON TRANSFER TO 2,3-DICHLOROPROPENE

A general synthesis of symmetrical biaryls in good to excellent yields via homo-coupling of aryl Grignard reagents in the presence of 2,3-dichloropropene is described.

HYDROLYTIC SELENOXIDE ELIMINATION REACTION FOR THE PREPARATION OF 2-CHLORO-1-OLEFINS

2-Chloro-1-olefins were synthesized in a regiocontrolled way from terminal olefins by a sequence involving Markownikoff-addition of PhSeCl, chlorination of the resulting β-chloroalkyl phenyl selenides with SO2Cl2 and, after recrystallization, hydrolysis/s