28145-35-9

Basic information

• Product Name: 4-(2-Chloroethyl) phenol
• Synonyms: 4-(2-Chloroethyl) phenol
• CAS NO: 28145-35-9
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.60946
• Mol File: 28145-35-9.mol

Chemical Properties

• Boiling Point: 274°C at 760 mmHg
• Flash Point: 119.5°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 0.00331mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 4-(2-Chloroethyl) phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Chloroethyl) phenol(28145-35-9)
• EPA Substance Registry System: 4-(2-Chloroethyl) phenol(28145-35-9)

Safety Data

• Hazardous Substances Data: 28145-35-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-(2-Chloroethyl) phenol is used as an intermediate in the production of various organic chemicals, including pesticides and pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of a wide range of compounds, contributing to the development of new products in these fields.
Used in Water Treatment:
In the water treatment industry, 4-(2-Chloroethyl) phenol is utilized as a fungicide, bactericide, and algaecide. Its antimicrobial properties make it effective in controlling the growth of unwanted microorganisms and algae in water systems, ensuring the maintenance of clean and safe water supplies.
Safety Considerations:
Given its potential irritant nature to the skin, eyes, and respiratory system, 4-(2-Chloroethyl) phenol requires careful handling. It is crucial to adhere to proper safety precautions and regulations when working with this chemical to minimize health risks and environmental impact.

InChI:InChI=1/C8H9ClO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6H2

Upstream product

• 501-94-0 p-hydroxyphenethyl alcohol 
• 81865-10-3 2-(4-aminophenyl)ethyl chloride 
• 3673-68-5 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol 
• 32327-70-1 1-chloro-4-(2-chloroethyl)benzene 
• 18995-35-2 4-tert-butoxychlorobenzene 
• 60876-70-2 4-tert-butoxybromobenzene 
• 106-48-9 4-chloro-phenol 
• 106-41-2 4-bromo-phenol 
• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 156-38-7 4-hydroxyphenylacetate 

Downstream Products

• 80565-11-3 4-{2-[2-(1⁽³⁾H-imidazol-4-yl)-ethylamino]-ethyl}-phenol 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 539-15-1 N,N-dimethyltyramine 
• 396124-49-5 ethyl 4-(2-chloroethyl)phenoxyacetate 
• 232946-67-7 HOC₆H₄(CH₂)2GeCl₃ 
• 78190-32-6 1-<(4-Hydroxy-phenyl)-ethyl>-pyrrolidin 
• 82966-19-6 1-<(4-Hydroxy-phenyl)-ethyl>-piperidin 
• 1009636-01-4 4-(2-(ethyl(methyl)amino)ethyl)phenol 
• 170962-05-7 4-(2-(diethylamino)ethyl)phenol 
• 910212-72-5 acetic acid 4-(2-chloroethyl)-phenyl ester 
• 910212-73-6 butyric acid 4-(2-chloro-ethyl)-phenyl ester 
• 910212-59-8 2-[5-(2-chloroethyl)-2-hydroxybenzyl-4-(2-chloroethyl)]phenol 
• 910212-71-4 2-bromo-4-(2-chloroethyl)-phenol 
• 910212-65-6 {6-[5-(2-chloro-ethyl)-2-hydroxy-phenyl]-6-oxo-hexyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers

Aiming to deepen the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.

Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates

While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.

Preparation method of p-(2-methoxyl)ethyl phenol

The invention discloses a preparation method of p-(2-methoxyl) ethyl phenol. According to the preparation method, p-chlorophenol is taken as the raw material, after etherification reactions, p-chlorophenol with a protected phenolic hydroxyl group is obtained, and after Grignard reactions, chlorination reactions, and methoxyl substitution reactions, p-(2-methoxyl)ethyl phenol is generated. The provided preparation method has the advantages of easily available raw materials, mild reaction conditions, high safety coefficient, strong operability, simple technology, easy industrialization, high product purity, and stable quality. The prepared p-(2-methoxyl)ethyl phenol totally meets the using requirements of medical intermediates.

Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with Molecular Oxygen

Photoredox-mediated copper-catalyzed hydroxylation of (hetero)aryl halides (including chlorides, bromides, and iodides) with O2 at room temperature has been developed. Preliminary mechanistic studies indicate no arylcopper intermediate and that aryl radicals are involved in this procedure. 18O-labeling experiments confirm the hydroxyl oxygen atom originated from molecular oxygen.

Phenol compound and preparation method

The invention relates to a phenol compound and a preparation method. In an organic solvent, aryl halide and oxygen or air are used as reaction raw materials, and under the combined facilitation effectof a copper catalyst, alkali and an additive, the aryl halide and the oxygen react in illumination of light to obtain the phenol compound. The copper catalyst and the alkali have key effects in a reaction process. The preparation method of the phenol compound has the advantages of wide substrate range, operation at room temperature, simple aftertreatment, high yield and purity of products and thelike. A new synthetic route and method are opened for the phenol compound, and thus, the phenol compound has good application potential and research value.

Structure–Activity Relationship Studies on 6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline Derivatives as Multidrug Resistance Reversers

A series of derivatives were synthesized and studied with the aim to investigate the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar. Then, different aryl-substituted amides were inserted, and to explore the effects of varying the amide function, the corresponding isosteric ester derivatives and some alkylamine analogues were synthesized. The new compounds were studied to evaluate their P-gp interaction profile and selectivity toward the two other ABC transporters, multidrug-resistance-associated protein-1 (MRP-1) and breast cancer resistance protein (BCRP). Investigation of the chemical stability of the amide and ester derivatives toward spontaneous or enzymatic hydrolysis showed that these compounds were stable in phosphate-buffered saline and human plasma. This study allowed us to evaluate the selectivity of the three series on the three efflux pumps and to propose the structural requirements that define the P-gp interaction profile. We identified two P-gp substrates, a P-gp inhibitor, and three ester derivatives that were active on BCRP, which opens a new scenario in the development of ligands active toward this pump.

N-(tert -butoxycarbonyl)- N -[(triethylenediammonium)sulfonyl]azanide: A convenient sulfamoylation reagent for alcohols

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl] azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ? tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

Development of chemical probes: Toward the mode of action of a methylene-linked di(aryl acetate) E1

Analogues of the novel inhibitor of the PI3-K/PKB pathway, 2-[5-(2-chloroethyl)-2-acetoxy-benzyl]-4-(2-chloroethyl)-phenyl acetate (E1), have been prepared and preliminary SAR performed. This established that at least one of the chloroethyl para-substituents could be removed or modified and the ability to inhibit PKB/Akt activation retained. Synthetic methodologies were then developed to methylene-linked aryl acetates for use as molecular probes to identify the target of compound E1.

Design, synthesis and evaluation of tacrine based acetylcholinesterase inhibitors

A series of tacrine based cholinesterase inhibitors was designed, synthesized and assayed for their biological activity. Among them, five compounds inhibited acetylcholinesterase in micromolar range and most of the compounds demonstrated much better selectivity for AChE than reference compound tacrine.

A method for parallel solid-phase synthesis of Lodinated analogues of the CB1 receptor inverse agonist rimonabant

A method for the parallel solid-phase synthesis (SPS) of iodinated analogues of Sanofi-Aventis' type 1 cannabinoid (CB1) receptor Inverse agonist rimonabant (acomplia) has been developed. The method allows the synthesis of a range of C3 amide/hydrazide derivatives from a resin-bound C3 ester precursor. The C-Ge linkage to the Hypogel-200 resin Is stable to the diversification conditions but allows ipsoiododegermylative cleavage using Nal/NCS even for the products containing the oxidatively labile hydrazide moiety.