2655-83-6

Basic information

• Product Name: 3-CHLOROPHENETOLE
• Synonyms: M-CHLOROETHOXYBENZENE;3-CHLOROPHENETOLE;Benzene, 1-chloro-3-ethoxy-;m-Chlorophenyl ethyl ether;Phenetole, m-chloro-;1-chloro-3-ethoxybenzene;3-Chlorophenylethyl ether;3-Chloroethoxybenzene
• CAS NO: 2655-83-6
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• EINECS: 220-185-3
• Product Categories: Phenetole;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 2655-83-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 86.5 °C12 mm Hg(lit.)
• Flash Point: 198 °F
• Appearance: /
• Density: 1.12 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.371mmHg at 25°C
• Refractive Index: n20/D 1.525(lit.)
• CAS DataBase Reference: 3-CHLOROPHENETOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROPHENETOLE(2655-83-6)
• EPA Substance Registry System: 3-CHLOROPHENETOLE(2655-83-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2655-83-6(Hazardous Substances Data)

Usage

General Description

3-Chlorophenetole, also known as 1-(3-chlorophenoxy)-2-propanol, is a chemical compound with the molecular formula C9H11ClO2. It is an organic compound that belongs to the family of phenols and is commonly used as a fragrance ingredient in various consumer products such as perfumes, lotions, and soaps. It is a colorless to pale yellow liquid with a floral odor and is soluble in organic solvents. 3-Chlorophenetole is synthesized through the reaction of 3-chlorophenol with epichlorohydrin in the presence of a base. It is considered to have low toxicity but can cause irritation to the skin, eyes, and respiratory system upon exposure. Additionally, it is important to handle this chemical with care and utilize proper safety measures when working with it.

InChI:InChI=1/C8H9ClO/c1-2-10-8-5-3-4-7(9)6-8/h3-6H,2H2,1H3

Upstream product

• 108-37-2 1-bromo-3-chlorobenzene 
• 141-52-6 sodium ethanolate 
• 121-73-3 3-Nitrochlorobenzene 
• 74-11-3 para-chlorobenzoic acid 
• 150-46-9 triethyl borate 
• 15163-60-7 p-chlorobenzoic acid potassium salt 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 3046-27-3 sodium m-chlorophenoxide 
• 108-43-0 3-monochlorophenol 
• 75-03-6 ethyl iodide 

Downstream Products

• 25117-75-3 3-(ethyloxy)benzonitrile 
• 108-43-0 3-monochlorophenol 
• 1304676-13-8 2,2-di(3-ethoxyphenyl)acetonitrile 
• 1204305-09-8 C₁₇H₁₃BrCl₂O₄ 
• 1016729-08-0 C₈H₈Cl₂O₃S 
• 334018-28-9 4-ethoxy-2-chloro-benzoic acid 
• 80524-88-5 4-chloro-2-hydroxy-benzenesulfonic acid 
• 99847-88-8 3-chloro-4-chloromethyl-phenetole 
• 245368-31-4 4-ethoxy-2-chloro-benzaldehyde 

Relevant articles and documents

Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides

An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.

Synthesis of aryl ethers from aromatic carboxylic acids

A silver/copper bimetallic catalyst system promotes the decarboxylative Chan-Evans-Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C-H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.

One-step preparation of some 3-substituted anisoles

A one-step preparation of 3-bromoanisole, 3-chloroanisole, and 3-trifluoromethylanisole from the corresponding 3-substituted nitrobenzenes is carried out by nucleophilic aromatic substitution of the nitro group with sodium or potassium methoxide, employing an effective amount of a phase-transfer catalyst (PTC), in a medium of a nonpolar aprotic solvent, under aerobic conditions, at a temperature of 50-65°C. The alkali methoxide used can be a pre-prepared solid, or it can be prepared in situ from the alkali hydroxide and methanol. The methoxydenitration proved to be very sensitive to the type of PTC. The effect of the solvent on the reaction is discussed. The targeted anisoles are obtained in yields of more than 80% and purities of greater than 99%.