3898-26-8

Basic information

• Product Name: (2-chloro-1-methoxyethyl)benzene
• Synonyms: (2-chloro-1-methoxyethyl)benzene;1-Phenyl-1-methoxy-2-chloroethane;Methyl(1-phenyl-2-chloroethyl) ether;Einecs 223-449-6
• CAS NO: 3898-26-8
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.63604
• EINECS: 223-449-6
• Mol File: 3898-26-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 219.7°Cat760mmHg
• Flash Point: 93.5°C
• Appearance: /
• Density: 1.085g/cm³
• Vapor Pressure: 0.174mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (2-chloro-1-methoxyethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2-chloro-1-methoxyethyl)benzene(3898-26-8)
• EPA Substance Registry System: (2-chloro-1-methoxyethyl)benzene(3898-26-8)

Safety Data

• Hazardous Substances Data: 3898-26-8(Hazardous Substances Data)

Usage

Description

(2-chloro-1-methoxyethyl)benzene, also known as o-Chloroanisole, is an aromatic chemical compound with the molecular formula C8H9ClO. It features a benzene ring with a chloro group and a methoxyethyl group attached, giving it a distinctive sweet, musty odor and a moldy or musty taste.

Uses

Used in Flavor and Fragrance Industry:
(2-chloro-1-methoxyethyl)benzene is used as a flavoring agent for its sweet, musty odor, adding unique taste and aroma profiles to various consumer products such as food, beverages, and pharmaceuticals.
Used in Wine and Cork Industry:
o-Chloroanisole is known for its ability to taint wine and cork, which can affect the sensory qualities of the final product. This property is utilized in the wine and cork industry to manage and control the impact of this compound on the taste and aroma of wines.
It is important to handle (2-chloro-1-methoxyethyl)benzene with care due to its potential harmful effects if inhaled, swallowed, or in contact with skin.

InChI:InChI=1/C9H11ClO/c1-11-9(7-10)8-5-3-2-4-6-8/h2-6,9H,7H2,1H3

Upstream product

• 100-42-5 styrene 
• 67-56-1 methanol 
• 593-78-2 methyl hypochlorite 
• 63603-28-1 1-methoxy-1-phenyl-2-phenylselenoethane 
• 116117-96-5 1-phenyl-1-methoxy-2-phenylselenenyl ethane dichloride 
• 37011-27-1 C₁₃H₁₇O₅Tl 

Downstream Products

• 81089-57-8 p-Nitro-α-methoxy-β-chloroethylbenzene 
• 81089-55-6 m-Nitro-α-methoxy-β-chloroethylbenzene 
• 81089-56-7 o-Nitro-α-methoxy-β-chloroethylbenzene 

Relevant articles and documents

Intermolecular Halogenation/Esterification of Alkenes with N-Halosuccinimide and Acetic Acid Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

1,4-Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N-chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans-chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N-bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Br?nsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems. (Figure presented.).

The vicinal functionalization of olefins: A facile route to the direct synthesis of β-chlorohydrins and β-chloroethers

An efficient and environmentally benign protocol for the synthesis of vicinal chlorohydroxy and chloromethoxy derivatives in a highly regioselective manner from olefins using NH4Cl as a chlorine source and oxone as an oxidant in aqueous acetone and methanol is demonstrated. This methodology offers an additive and metal chloride free approach and is endowed with simple reaction conditions, high yields a broad substrate scope and good functional group tolerance. Moreover, the aromatic substrates with a terminal double bond exhibited merely Markovnikov selectivity, while the internal alkenes show exclusive regiocontrol and low to moderate diastereoselectivity.

(Dichloroiodo)benzene - An Easily Available Reagent for Chloro- and Iodoalkoxylation, Iodohydroxylation, and Iodochlorination of Alkenes

A convenient synthesis of vicinal methoxychlorides, methoxyiodides, iodhydrines and iodochloride from alkenes using PhICl2/CH 3OH, I2/ PhICl2/CH3OH, I 2/PhICl2/CH3CN/H2O and I 2/PhICl2/CH2Cl2 is described.