886-58-8

Basic information

• Product Name: 1-benzyl-4-(propan-2-yl)benzene
• Synonyms: 1-Benzyl-4-isopropylbenzene; 4-Isopropyldiphenylmethane; benzene, 1-(1-methylethyl)-4-(phenylmethyl)-
• CAS NO: 886-58-8
• Molecular Formula: C₁₆H₁₈
• Molecular Weight: 210.3141
• Mol File: 886-58-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 303.1°C at 760 mmHg
• Flash Point: 140.5°C
• Density: 0.96g/cm³
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 1-benzyl-4-(propan-2-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-(propan-2-yl)benzene(886-58-8)
• EPA Substance Registry System: 1-benzyl-4-(propan-2-yl)benzene(886-58-8)

Safety Data

• Hazardous Substances Data: 886-58-8(Hazardous Substances Data)

Upstream product

• 98-82-8 Isopropylbenzene 
• 100-51-6 benzyl alcohol 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 5281-18-5 benzaldehyde, hydrazone 
• 203788-13-0 4-isopropylphenyl tosylate 
• 100-52-7 benzaldehyde 
• 2051-18-5 4-isopropylbenzyl chloride 
• 98-80-6 phenylboronic acid 
• 98-88-4 benzoyl chloride 
• 64-17-5 ethanol 
• 18864-76-1 4-isopropylbenzophenone 
• 100-44-7 benzyl chloride 

Downstream Products

• 54965-61-6 1-cyclohexylmethyl-4-isopropyl-cyclohexane 

Relevant articles and documents

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions

Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

Bisulfate Salt-Catalyzed Friedel-Crafts Benzylation of Arenes with Benzylic Alcohols

We report here a method of direct Friedel-Crafts benzylation of arenes with benzylic alcohols using cheap and readily available bisulfate salt as the catalyst in hexafluoroisopropanol. The catalytic system is powerful with a quite diverse group of functionalized arenes and benzylic alcohols. These mild conditions provide a straightforward synthesis of a variety of unsymmetrical diarylmethanes in high yield with good to high regioselectivity. An SN1 mechanism involving activation of the hydroxy group through a hydrogen bond is proposed.

Synthesis of diarylmethanes via a Friedel-Crafts benzylation using arenes and benzyl alcohols in the presence of triphenylphosphine ditriflate

Triphenylphosphine ditriflate (TPPD) was found to be an efficient promoter for the Friedel-Crafts benzylation of arenes with benzyl alcohols in CH 2Cl2 at room temperature. The good yields, the 1:1 molar ratio of arene and benzyl alcohol, the benzylation of chlorobenzene as a nonactivated aromatic compound at room temperature, and no by-product formation are the main advantages of this procedure.