54870-22-3

Basic information

• Product Name: (3,3-dichloropropyl)benzene
• CAS NO: 54870-22-3
• Molecular Formula: C₉H₁₀Cl₂
• Molecular Weight: 189.0817
• Mol File: 54870-22-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 255.1°C at 760 mmHg
• Flash Point: 118.9°C
• Density: 1.167g/cm³
• Vapor Pressure: 0.0266mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: (3,3-dichloropropyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (3,3-dichloropropyl)benzene(54870-22-3)
• EPA Substance Registry System: (3,3-dichloropropyl)benzene(54870-22-3)

Safety Data

• Hazardous Substances Data: 54870-22-3(Hazardous Substances Data)

Upstream product

• 75-01-4 chloroethylene 
• 100-44-7 benzyl chloride 
• 104-53-0 3-phenyl-propionaldehyde 
• 112471-51-9 2-(3-phenylpropoxy)tetrahydro-2H-pyran 
• 14629-60-8 trimethyl(3-phenylpropoxy)silane 
• 42956-39-8 1,1,3-trichloro-3-phenylpropane 
• 100-42-5 styrene 
• 67-66-3 chloroform 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 2038-57-5 3-Phenylpropan-1-amine 

Downstream Products

• 1379610-52-2 4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane 
• 673-32-5 1-Phenylprop-1-yne 
• 6268-37-7 (3-chloro-2-propenyl)-benzene 

Relevant articles and documents

One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system

A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry.

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

The use of low-cost manganese(II) bromide (MnBr2) and tetramethylethylenediamine (TMEDA) catalyzes the cross coupling of (bis)pinacolatodiboron with a wide range of alkyl halides, demonstrating the first manganese-catalyzed coupling with alkyl electrophiles. This method allows access to primary, secondary, and tertiary boronic esters from the parent chlorides, which were previously inaccessible as coupling partners. The reaction proceeds in high yield with as little as 1000 ppm catalyst loading, while 5 mol % can provide high yields in as little as 30 min. Finally, radical-clock experiments revealed that at 0 °C direct borylation outcompetes alternative radical processes, thereby providing synthetically useful, temperature-controlled reaction outcomes.