55736-04-4

Basic information

• Product Name: 1-(2-Chloro-6-hydroxyphenyl)ethanone
• Synonyms: 1-(2-Chloro-6-hydroxyphenyl)ethanone;2'-Chloro-6'-hydroxyacetophenone;Ethanone, 1-(2-chloro-6-hydroxyphenyl)-;1-(2-Chloro-6-hydroxyphenyl)
• CAS NO: 55736-04-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.594
• Mol File: 55736-04-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 225.4°C at 760 mmHg
• Flash Point: 90.1°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 0.058mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.20±0.10(Predicted)
• CAS DataBase Reference: 1-(2-Chloro-6-hydroxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chloro-6-hydroxyphenyl)ethanone(55736-04-4)
• EPA Substance Registry System: 1-(2-Chloro-6-hydroxyphenyl)ethanone(55736-04-4)

Safety Data

• Hazardous Substances Data: 55736-04-4(Hazardous Substances Data)

Usage

Uses

1-(2-Chloro-6-hydroxyphenyl)ethanone is used for synthesis and structure-activity relationship of novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors.

Preparation

Preparation by diazotization of 2-amino-6-chloro-acetophenone, followed by hydrolysis of the obtained diazonium salt (55%).

InChI:InChI=1/C8H7ClO2/c1-5(10)8-6(9)3-2-4-7(8)11/h2-4,11H,1H3

Upstream product

• 881883-32-5 1-(2-Chloro-6-methoxy-phenyl)-ethanone 
• 6575-10-6 2-Chlor-6-methoxybenzoesaeurenitril 
• 91105-99-6 1-chloro-3-(methoxymethoxy)benzene 
• 108-43-0 3-monochlorophenol 
• 89999-90-6 3-chloro-2-cyanophenol 
• 75-16-1 methylmagnesium bromide 
• 211449-30-8 2-acetyl-3-chlorophenyl diethylcarbamate 

Downstream Products

• 1227415-97-5 C₂₀H₁₅ClN₄O₃ 
• 1263427-05-9 tert-butyl 5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 1263427-06-0 5-chloro-4-phenylspiro[chromene-2,4'-piperidine] 
• 1263427-07-1 tert-butyl {5-[2-(5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-1,3-thiazol-5-yl]-2H-tetrazol-2-yl}acetate 
• 1263426-57-8 {5-[2-(5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-1,3-thiazol-5-yl]-2H-tetrazol-2-yl}acetic acid 
• 1354928-51-0 C₁₇H₁₁ClO₄ 
• 1354928-57-6 C₁₇H₁₁ClO₄ 
• 1441774-34-0 C₁₈H₁₇ClO₅ 
• 1441771-84-1 5-chloro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 1241953-54-7 5-chloro-3,4-dihydrospiro[chromene-2,4'-piperidine] hydrochloride 

Relevant articles and documents

Chromenones as potent bradykinin B1 antagonists

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone 15 was efficacious in a carrageenan-induced mechanical hyperalgesia model for chronic pain.

NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE

Heteroaromatic compounds of structural formula I are selective inhibitors of stearoyl- coenzyme. A delta-9 desaturase (SCDl) relative to other known stearoyl-coenzyme. A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis. Formula (I).

Synthesis and evaluation of novel stearoyl-CoA desaturase 1 inhibitors: 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-3, 4-dihydrospiro[chromene-2,4′-piperidine] analogs

In continuation of our investigation on novel stearoyl-CoA desaturase (SCD) 1 inhibitors, we have already reported on the structural modification of the benzoylpiperidines that led to a series of novel and highly potent spiropiperidine-based SCD1 inhibitors. In this report, we would like to extend the scope of our previous investigation and disclose details of the synthesis, SAR, ADME, PK, and pharmacological evaluation of the spiropiperidines with high potency for SCD1 inhibition. Our current efforts have culminated in the identification of 5-fluoro-1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol- 2-yl]pyridazin-3-yl}-3,4-dihydrospiro[chromene-2,4′-piperidine] (10e), which demonstrated a very strong potency for liver SCD1 inhibition (ID 50 = 0.6 mg/kg). This highly efficacious inhibition is presumed to be the result of a combination of strong enzymatic inhibitory activity (IC 50 (mouse) = 2 nM) and good oral bioavailability (F >95%). Pharmacological evaluation of 10e has demonstrated potent, dose-dependent reduction of the plasma desaturation index in C57BL/6J mice on a high carbohydrate diet after a 7-day oral administration (q.d.). In addition, it did not cause any noticeable skin abnormalities up to the highest dose (10 mg/kg).