167145-13-3

Basic information

• Product Name: 2-[2-(3-Methoxyphenyl)ethyl]phenol
• Synonyms: 2-(2-(3-METHOXYPHENYL)ETHYL)PHENOL;Phenol, 2-[2-(3-methoxyphenyl)ethyl]-;2-[2-(3-Methoxypheny;2-(3-methoxyphenethyl)phenol
• CAS NO: 167145-13-3
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.29
• EINECS: 1806241-263-5
• Product Categories: strong recommend
• Mol File: 167145-13-3.mol

Chemical Properties

• Melting Point: 45.0 to 49.0 °C
• Boiling Point: 347.611 °C at 760 mmHg
• Flash Point: 167.889 °C
• Appearance: /
• Density: 1.112 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.30±0.30(Predicted)
• CAS DataBase Reference: 2-[2-(3-Methoxyphenyl)ethyl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(3-Methoxyphenyl)ethyl]phenol(167145-13-3)
• EPA Substance Registry System: 2-[2-(3-Methoxyphenyl)ethyl]phenol(167145-13-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 167145-13-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[2-(3-Methoxyphenyl)ethyl]phenol is used as an intermediate for the synthesis of sarpogrelate (S142300, HCl salt) analogues. The primary application reason for its use is to facilitate the creation of sarpogrelate hydrochloride, which is a potent and selective 5-HT2A receptor antagonist. 2-[2-(3-Methoxyphenyl)ethyl]phenol has demonstrated its effectiveness as an antiplatelet agent, making it a valuable component in the development of medications aimed at treating various cardiovascular conditions.
Additionally, due to its role in the synthesis of sarpogrelate analogues, 2-[2-(3-Methoxyphenyl)ethyl]phenol may also contribute to the development of other pharmaceutical compounds with potential therapeutic applications, further expanding its utility within the industry.

InChI:InChI=1/C15H16O2/c1-17-14-7-4-5-12(11-14)9-10-13-6-2-3-8-15(13)16/h2-8,11,16H,9-10H2,1H3

Upstream product

• 90-02-8 salicylaldehyde 
• 2398-37-0 3-methoxyphenyl bromide 
• 1711-05-3 m-anisoyl chloride 
• 553-86-6 benzofuran-2(3H)-one 
• 60815-18-1 diethyl [(3-methoxyphenyl)methyl]phosphonate 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 5533-04-0 2-(methoxymethoxy)benzaldehyde 
• 1072930-86-9 1-[benzyloxy]-2-[2-(3-methoxyphenyl)ethenyl]benzene 
• 33223-21-1 C₂₆H₂₄ClOP 
• 824-98-6 m-methoxybenzyl chloride 
• 18880-05-2 3-methoxybenzyl-triphenylphosphonium chloride 

Downstream Products

• 167143-55-7 1-t-butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidine 
• 1026081-58-2 (S)-2-{2-[2-(3-Methoxy-phenyl)-ethyl]-phenoxymethyl}-pyrrolidine-1-carboxylic acid ethyl ester 
• 167143-27-3 1-tert-butoxycarbonyl-4-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]piperidine 
• 167143-51-3 1-tert-butoxycarbonyl-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl]piperidine 
• 167143-47-7 1-t-butoxycarbonyl-2-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine 
• 167143-43-3 4-t-butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}morpholine 
• 167145-78-0 (S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine 
• 167145-80-4 (R)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine 
• 191091-81-3 (S)-1-ethoxycarbonyl-2-[3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]propyl]pyrrolidine 
• 167143-59-1 1-t-butoxycarbonyl-4-(2-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}ethyl)piperidine 
• 167145-83-7 (2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine 
• 191091-77-7 (2S,4R)-4-Benzyloxy-2-(2-{2-[2-(3-methoxy-phenyl)-ethyl]-phenoxy}-ethyl)-pyrrolidine-1-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation method of sarpogrelate hydrochloride intermediate

The invention discloses a preparation method of sarpogrelate hydrochloride intermediate (2-hydroxy-3'-methoxy diphenylethane). According to the preparation method, m-bromoanisole, ethane, and o-benzyloxybromobenzene are taken as initial raw materials, an inorganic base is taken as an auxiliary agent, a palladium catalyst is adopted for catalysis, and o-benzoxy-3'-methoxy toluylene is obtained via reaction; o-benzoxy-3'-methoxy toluylene is subjected to hydrogenation debenzylation so as to obtain 2-hydroxy-3'-methoxy diphenylethane. The raw materials are common chemical raw materials, are cheap, and are high in safety; separation of by-products obtained in reaction process is relatively simple; separation is complete; steps are few; on-pot-method is adopted; and product yield is increased.

Preparation methods of 2-phenethyl phenol derivative and intermediate of 2-phenethyl phenol derivative as well as intermediate

The invention discloses a preparation method of a 2-phenethyl phenol derivative. The preparation method of the 2-phenethyl phenol derivative comprises following steps: a compound represented in a formula 5 is subjected to a reduction reaction, a compound represented in a formula 1 is prepared, wherein the compound represented in the formula 5 is prepared from a compound represented in a formula 4 through an ester hydrolysis reaction and a decarboxylic reaction, the compound represented in the formula 4 is prepared from a compound represented in a formula 2 and a compound represented in a formula 3 through a condensation reaction, and R is hydrogen, halogen, C1-C3 alkyl or C1-C3 alkoxy. The preparation methods of the 2-phenethyl phenol derivative and an intermediate of the 2-phenethyl phenol derivative are low in cost and safe to operate, the steps and the after-treatment are simple, a few by-products are produced, the intermediate product and the final product are both easy to purify, the total yield and the purity are higher, and industrial production is facilitated.

A 2 - [2 - (3-methoxy-phenyl)-ethyl]-phenol synthesis method

The invention discloses a synthetic method for 2-[2-(3-methoxyphenyl)ethyl]phenol. The method comprises: firstly synthesizing diethyl 3-methoxybenzylphosphonate and 2,2-dimethoxybenzaldehyde, then successively synthesizing 1-(2,2-dimethoxyphenyl)-2-(3-methoxyphenyl)ethylene, 1-(2-phenoxy)-2-(3-methoxyphenyl)ethylene, 1-(2-acetoxphenyl)-2-(3-methoxyphenyl)ethylene and 1-(2-acetoxphenyl)-2-(3-methoxyphenyl)ethane, and finally synthesizing the product 2-[2-(3-methoxyphenyl)ethyl]phenol. The prepared 2-[2-(3-methoxyphenyl)ethyl]phenol product is good in quality and high in yield.

Synthetic method of sarpogrelate intermediate 2-[2-(3-methoxyphenyl)ethyl]phenol

The invention discloses a synthetic method of a sarpogrelate intermediate 2-[2-(3-methoxyphenyl)ethyl]phenol and relates to the technical field of organic synthesis. In the method, with m-methoxyl chlorobenzene, which is easy to obtain and is low in cost, as a raw material, the method includes the steps of: 1) performing condensation to the raw material with triethyl phosphite; and 2) performing condensation with o-phenylmethoxyl benzaldehyde (which is prepared from salicylic acid and chlorobenzene), performing hydrogenation to alkylate a double bond, and crystallizing a product with petroleum ether to prepare a white crystal target product. The method simplifies process steps, reduces loss ratio and is 99.5% in product purity. The 2-[2-(3-methoxyphenyl)ethyl]phenol is used for preparing sarpogrelate hydrochloride, wherein single impurity is less than 0.1% in content and the product purity reaches more than 99.8%.

SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity

Starting from the previously developed P-gp ligands 1a and 1b (EC 50 = 0.25 μM and 0.65 μM, respectively), new arylmethyloxyphenyl derivatives have been synthesized as P-gp modulators in order to investigate: (i) the effect of small electron-do

A practical synthesis of sarpogrelate hydrochloride and in vitro platelet aggregation inhibitory activities of its analogues

A convenient approach for the preparation of sarpogrelate hydrochloride was developed. Two series of sarpogrelate hydrochloride analogues were designed and synthesized in order to improve their platelet aggregation inhibitory activities, biological tests suggested that these compounds have platelet aggregation inhibitory activities to some extent.

Arylmethyloxyphenyl derivatives: Small molecules displaying P-glycoprotein inhibition

Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D 2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [3H]vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.

Syntheses and Platelet Aggregation Inhibitory and Antithrombotic Properties of ethyl>benzenes

A series of ethyl>benzene derivatives were synthesized and evaluated for their ability to inhibit collagen-induced platelet aggregation in vitro and to protect experimantal thrombosis in mice.The results showed that the compounds were in vitro inhibitors of collagen-induced platelet aggregation.Most of them were also effective in the mouse antithrombotic assay.The compounds were found to be potent antagonists to S2 serotonergic receptor, and good correlation (r = 0.85) between their S2 serotonergic receptor antagonism and their potency as platelet antiaggregatory drugs was observed.Among the compounds studied, monophenoxy>methyl>ethyl>succinate hydrochloride (12b, MCI-9042) was selected for further pharmacological and toxicological evaluation.