6165-52-2

Basic information

• Product Name: 4-(1-phenylethyl)-m-xylene
• Synonyms: 4-(1-phenylethyl)-m-xylene;Benzene, 2,4-dimethyl-1-(1-phenylethyl)-;1-(1-Phenylethyl)-2,4-dimethylbenzene;1-Phenyl-1-(2,4-dimethylphenyl)ethane;1-Phenyl-1-(2,4-xylyl)ethane;4-(α-Methylbenzyl)-m-xylene;1,3-Dimethyl-4-(1-phenylethyl)benzene;Einecs 228-202-6
• CAS NO: 6165-52-2
• Molecular Formula: C₁₆H₁₈
• Molecular Weight: 210.31412
• EINECS: 228-202-6
• Mol File: 6165-52-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: -54 °C
• Boiling Point: 305.3°C at 760 mmHg
• Flash Point: 142.1°C
• Appearance: /
• Density: 0.961g/cm³
• Vapor Pressure: 0.0015mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 4-(1-phenylethyl)-m-xylene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-phenylethyl)-m-xylene(6165-52-2)
• EPA Substance Registry System: 4-(1-phenylethyl)-m-xylene(6165-52-2)

Safety Data

• Hazardous Substances Data: 6165-52-2(Hazardous Substances Data)

Usage

General Description

4-(1-phenylethyl)-m-xylene is a chemical compound with the formula C20H20. It is a type of xylene, which is a common solvent and chemical intermediate. This specific compound contains a phenylethyl group attached to the meta position of the xylene molecule. It is used in various industrial processes, including the production of polymers, plastics, and synthetic fibers. Additionally, it can be found in adhesives, coatings, and paint thinners. It is important to handle this chemical with caution, as it can be harmful if ingested, inhaled, or comes into contact with the skin or eyes. Overall, 4-(1-phenylethyl)-m-xylene plays a crucial role in the production of many everyday products but should be handled and used with care due to its potential hazards.

InChI:InChI=1/C16H18/c1-12-9-10-16(13(2)11-12)14(3)15-7-5-4-6-8-15/h4-11,14H,1-3H3

Upstream product

• 100-42-5 styrene 
• 108-38-3 m-xylene 
• 98-86-2 acetophenone 
• 98-85-1 1-Phenylethanol 
• 89-74-7 2,4-dimethylacetophenone. 
• 24947-01-1 2,4-dimethyl-1-(1-phenylethenyl)benzene 

Downstream Products

• 34557-54-5 methane 
• 120-12-7 anthracene 

Relevant articles and documents

Cascade Reductive Friedel-Crafts Alkylation Catalyzed by Robust Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand

The synthesis of complex molecules like active pharmaceutical ingredients typically requires multiple single-step reactions, in series or in a modular fashion, with laborious purification and potentially unstable intermediates. Cascade processes offer attractive synthetic remediation as they reduce time, energy, and waste associated with multistep syntheses. For example, triarylmethanes are traditionally prepared via several synthetic steps, and only a handful of cascade routes are known with limitations due to high catalyst loadings. Here, we present an expedient catalytic cascade process to produce triarylmethanes. For this purpose, we have developed a bifunctional iridium system as the efficient catalyst to build heterotriaryl synthons via reductive Friedel-Crafts alkylation from ketones, arenes, and hydrogen. The catalytically active species were generated in situ from a robust triazolyl iridium(III) hydride complex and acid and is composed of a metal-bound hydride and a proximal ligand-bound proton for reversible dihydrogen release. These complexes catalyze the direct hydrogenation of ketones at slow rates followed by dehydration. Appropriate adjustment of the conditions successfully intercepts this dehydration and leads instead to efficient C-C coupling and Friedel-Crafts alkylation. The scope of this cascade process includes a variety of carbonyl substrates such as aldehydes, (alkyl)(aryl)ketones, and diaryl ketones as precursor electrophiles with arenes and heteroarenes for Friedel-Crafts coupling. The reported method has been validated in a swift one-step synthesis of the core structure of a potent antibacterial agent. Excellent yields and exquisite selectivities were achieved for this cascade process with unprecedentedly low iridium loadings (0.02 mol %). Moreover, the catalytic activity of the protic system is significantly higher than that of an N-methylated analogue, confirming the benefit of the Ir-H/N-H hydride-proton system for high catalytic performance.

A surprising substituent effect provides a superior boronic acid catalyst for mild and metal-free direct Friedel-Crafts alkylations and prenylations of neutral arenes

The development of more general and efficient catalytic processes for Friedel-Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5-tetrafluorophenylboronic acid was identified as a potent air- and moisture-tolerant metal-free catalyst that significantly improves the scope of direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.

Iron-catalyzed arylation of aromatic ketones and aldehydes mediated by organosilanes

A simple and efficient iron-catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4-% FeCl3 or Fe(acac) 3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel-Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel-Crafts alkylation reactions, robust applications for the synthesis of pharmaceutical intermediates and so on can be envisioned. A robust one-pot, iron-catalyzed chlorination Friedel-Crafts alkylation reaction of benzylic carbonyl compounds, mediated by chlorotrimethylsilane and triethylsilane, has been developed to yield substituted diaryl and triaryl building blocks. Copyright