3898-26-8

Usage

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 (2-chloro-1-methoxyethyl)benzene 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 academic research and scientific papers

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.).

Cross-Linked Artificial Enzyme Crystals as Heterogeneous Catalysts for Oxidation Reactions

Designing systems that merge the advantages of heterogeneous catalysis, enzymology, and molecular catalysis represents the next major goal for sustainable chemistry. Cross-linked enzyme crystals display most of these essential assets (well-designed mesoporous support, protein selectivity, and molecular recognition of substrates). Nevertheless, a lack of reaction diversity, particularly in the field of oxidation, remains a constraint for their increased use in the field. Here, thanks to the design of cross-linked artificial nonheme iron oxygenase crystals, we filled this gap by developing biobased heterogeneous catalysts capable of oxidizing carbon-carbon double bonds. First, reductive O2 activation induces selective oxidative cleavage, revealing the indestructible character of the solid catalyst (at least 30 000 turnover numbers without any loss of activity). Second, the use of 2-electron oxidants allows selective and high-efficiency hydroxychlorination with thousands of turnover numbers. This new technology by far outperforms catalysis using the inorganic complexes alone, or even the artificial enzymes in solution. The combination of easy catalyst synthesis, the improvement of "omic" technologies, and automation of protein crystallization makes this strategy a real opportunity for the future of (bio)catalysis.

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.

Thiourea catalysis of NCS in the synthesis of β-chloroethers

Thiourea catalysis of olefin chlorination with NCS in an alcohol gives β-chloroethers with a very fast reaction of high yield.

(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.

4,4′-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid: New recyclable hypervalent iodine reagents for vicinal halomethoxylation of unsaturated compounds

4,4′-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid are convenient recyclable hypervalent iodine reagents for vicinal chloromethoxylation or iodomethoxylation of unsaturated compounds. The reactivity of these reagents in the reaction of vicinal halomethoxylation is generally similar to dichloroiodobenzene and the advantage of their use is that the reduced forms of these reagents can be easily separated from the reaction mixture and reused for the regeneration of the reagents.

Trichloroisocyanuric Acid as a Cohalogenating Reagent: An Efficient Transformation of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates

The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid (0.34 mol equiv) in alcohols (MeOH, EtOH, i-PrOH, t-BuOH), acetic acid or aqueous acetone, respectively.

ANODIC FUNCTIONALIZATION OF OLEFINS IN ALCOHOLS IN THE PRESENCE OF HALIDE SALTS

Electrolysis of conjugated, unbranched arylolefins in the presence of alkali metal halides in alcohols affords 1-aryl-2-bromoketals in 60-90percent yields.Under these conditions, 2-methyl-1-phenylprop-1-ene is converted into 1-bromo-2-methyl-1-phenylprop-1-ene in 80percent yield, and arylolefins with no benzylidene hydrogens give 1-aryl-1-alkoxy-2-bromoalkanes.

A Novel Method for the Conversion of Halide Anion to the Positive Halogen by Nitrobenzenesulfonyl Peroxide. Application to Oxyhalogenation of Olefin

Bromide and chloride anions could be readily oxidized into positive halogens by treating with p-nitrobenzenesulfonyl peroxide.The positive halogens, thus formed, reacted with olefins to give epihalonium ions, which were trapped by oxygen nucleophiles inter- or intramolecularly to afford oxyhalogenated compounds.