Ethylbenzyl chloride

• CAS: 26968-58-1
• Catalog Number: ACM26968581
• Category: Main Products
• Molecular Weight: 154.64
• Molecular Formula: C9H11Cl
• Synonyms: (chloromethyl)ethyl-benzen;P-ETHYLBENZYL CHLORIDE;ETHYL BENZYL CHLORIDE;(chloromethyl)ethyl-benzene;4-ETHYLBENZYL CHLORIDE;Benzene, (chloromethyl)ethyl;Benzene,(chloromethyl)ethyl;Ethylbenzyl chloride, isomer mixture
• IUPAC Name: 1-chloropropylbenzene
• Canonical SMILES: CCC(C1=CC=CC=C1)Cl
• InChI Key: MZMVVHAHSRJOEO-UHFFFAOYSA-N
• Boiling Point: 111ºC at 25mmHg
• Melting Point: -21ºC
• Flash Point: 82.7ºC
• Density: 1.031 g/cm³
• Appearance: Colorless clear liquid
• Exact Mass: 154.05500

Case Study

Efficient synthesis of ethylbenzonitrile by ethylbenzyl chloride

Xie, Guangyong, and Aiqing Zhang. Synthetic Communications 42.3 (2012): 375-379.

Ethylbenzonitrile is synthesized by selective gas phase oxidation of ethylbenzyl chloride, which was synthesized for the first time at about 200 degrees Celsius in good yield and almost 100% selectivity. Ethylbenzonitrile was synthesized by selective oxidation of ethylbenzyl chloride prepared by chloromethylation of ethylbenzene in high yield and with low temperature selectivity close to 100%. This method provides a new route for alkylbenzonitriles and other aromatic nitriles.
The selective oxidation of ethylbenzyl chloride was carried out in a 30 mm inner diameter quartz tube fixed bed reactor loaded with 10 g of catalyst. Chloroethylbenzoyl fluoride was fed with a micro pump, vaporized, and mixed with ammonia and air in a preheated container after passing through a gas flow meter with an appropriate molar ratio. The preheated gas stream was then fed directly into the reactor. The temperature was maintained at 210 2 C. Ethylbenzyl chloride (EBC) was fed at a rate of 0.6 ml per hour. After the reaction, the outlet flow was cooled and the product was condensed in a condensation unit with a yield of 95%. The reaction could be carried out continuously. The condenser was replaced every 8 h and the test lasted for nearly 80 h. Pure o-ethylbenzonitrile and p-ethylbenzonitrile were obtained by fractionation with yields of 32% and 66%, respectively, and GC purities of 98% and 99%. The structure of the product was confirmed by comparison with IR and H NMR.

Intrinsic fluorescence properties of microspheres investigated using p-ethylbenzyl chloride

Qu, Jian-Bo, et al. Colloids and Surfaces B: Biointerfaces 152 (2017): 475-481.

Commercially available polystyrene (PS) fluorescent microspheres are widely used in biological applications such as tracing, in vivo imaging, and flow cytometry calibration. However, these particles do have some drawbacks, such as leakage of organic dyes therein and photobleaching. This study explored for the first time the intrinsic fluorescence properties of PS-based microspheres. Here, it was found that a simple chloromethylation reaction endowed polystyrene particles with intrinsic fluorescence without any subsequent external fluorophore coupling. The possible mechanism of fluorescence was elucidated by synthesizing and studying p-ethylbenzyl chloride. Notably, no photobleaching or leakage issues were observed due to the stable structure of the microspheres. Chloromethylated PS (CMPS) microspheres retain their permanent blue fluorescence even in the dry powder state, making them an attractive coating material.
p-ethylbenzyl chloride exhibits bright blue-green fluorescence when excited at 365 nm. Similar to CMPS and CMPS-PEG microspheres, p-ethylbenzyl chloride observed a strong emission band between 400 and 600 nm at around 440 nm. Neither ethylbenzene nor chloromethyl ether fluoresced when irradiated at 365 nm, indicating that the fluorescence of p -ethylbenzyl arises from the rigid conjugated structure developed by the Friedel-Crafts reaction of ethylbenzene and chloromethyl ether.

Custom Q&A

What is the molecular formula of ethylbenzyl chloride?

The molecular formula of ethylbenzyl chloride is C9H11Cl.

What are the synonyms of ethylbenzyl chloride?

The synonyms of ethylbenzyl chloride are (1-chloropropyl)benzene, 934-11-2, and 1-chloropropylbenzene.

What is the molecular weight of ethylbenzyl chloride?

The molecular weight of ethylbenzyl chloride is 154.63 g/mol.

Is ethylbenzyl chloride soluble in water?

No, ethylbenzyl chloride is insoluble in water.

What are the potential hazards of ethylbenzyl chloride?

Ethylbenzyl chloride may irritate the skin, eyes, and mucous membranes. It may also be toxic if ingested.

How is ethylbenzyl chloride used?

Ethylbenzyl chloride is used to make other chemicals.

What is the IUPAC name of ethylbenzyl chloride?

The IUPAC name of ethylbenzyl chloride is 1-chloropropylbenzene.

What is the InChI of ethylbenzyl chloride?

The InChI of ethylbenzyl chloride is InChI=1S/C9H11Cl/c1-2-9(10)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3.

What is the CAS number of ethylbenzyl chloride?

The CAS number of ethylbenzyl chloride is 26968-58-1.

What is the physical description of ethylbenzyl chloride?

Ethylbenzyl chloride appears as a colorless to pale-colored liquid with a pungent odor. It is slightly denser than water.