1450-74-4

Basic information

• Product Name: 1-(5-Chloro-2-hydroxyphenyl)ethanone
• Synonyms: ASISCHEM D38764;2'-HYDROXY-5'-CHLORO ACETOPHENONE;2-HYDROXY-5-CHLORO ACETOPHENONE;1-(5-CHLORO-2-HYDROXYPHENYL)-1-ETHANONE;1-(5-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE;1-(5-CHLORO-2-HYDROXYPHENYL)ETHANONE;AKOS BB-6937;5'-CHLORO-2'-HYDROXYACETOPHENONE
• CAS NO: 1450-74-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 215-916-8
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Phenoles and thiophenoles;Adehydes, Acetals & Ketones;Chlorine Compounds;Phenols;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 1450-74-4.mol
• Article Data: 54

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 126-128 °C28 mm Hg(lit.)
• Flash Point: 107-109°C/12mm
• Appearance: slightly yellow crystalline powder or chunks
• Density: 1.2315 (rough estimate)
• Refractive Index: 1.5590 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.72±0.18(Predicted)
• BRN: 1365589
• CAS DataBase Reference: 1-(5-Chloro-2-hydroxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-Chloro-2-hydroxyphenyl)ethanone(1450-74-4)
• EPA Substance Registry System: 1-(5-Chloro-2-hydroxyphenyl)ethanone(1450-74-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1450-74-4(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow crystalline powder or chunks

Uses

5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) may be used in the synthesis of:6-chloro-2-methyl-4H-chrome-4-one1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones2-styrenyl allyl ether

Preparation

Preparation by Fries rearrangement of 4-chlorophenyl acetate with aluminium chloride without solvent between 110° and 200°(90–100% yield).

General Description

5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) on condensation with salicylhydrazide yields Schiff base, which is reported to form copper(II) complexes. Dipole moment of 5-chloro-2- hydroxyacetophenone has been evaluated in benzene solution.

Synthetic route

1-(2-(allyloxy)-5-chlorophenyl)ethan-1-one (186956-36-5) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
With iodine at 20℃;	94%

4-chlorophenyl acetate (876-27-7) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
With hydrogen fluoride supported on silica gel In neat (no solvent) at 55℃; for 4h; Green chemistry;	91%
With aluminum (III) chloride In neat (no solvent) at 140 - 150℃; Fries Phenol Ester Rearrangement;	90%
With potassium carbonate In hexane at 25℃; for 12h; Irradiation;	88%

3-methyl-1,2-benzisoxazole 2-oxide (75632-99-4) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
With hydrogenchloride In ethanol; water for 12h; Heating;	90%

acetic anhydride (108-24-7) + 4-chloro-phenol (106-48-9) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
Stage #1: acetic anhydride; 4-chloro-phenol Stage #2: With boron trifluoride diacetate In neat (no solvent) Fries Phenol Ester Rearrangement;	77%

5'-chloro-2'-hydroxyacetophenoneoxime (87974-51-4, 29725-93-7) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
With sodium perborate In acetic acid for 3.5h; deoximation; Heating;	75%

o-hydroxyacetophenone (118-93-4) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
Stage #1: o-hydroxyacetophenone In acetonitrile at 80℃; for 0.166667h; Stage #2: With N-chloro-succinimide In acetonitrile at 80℃; for 8h; regioselective reaction;	71%
With N-chloro-succinimide; toluene-4-sulfonic acid In acetonitrile at 20℃; for 4h; regioselective reaction;	70%
Stage #1: o-hydroxyacetophenone With toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-chloro-succinimide In water; acetonitrile at 20℃; for 2h; regioselective reaction;	49%

4-chloro-phenol (106-48-9) + acetyl chloride (75-36-5) → 5-chloro-2-hydroxyacetophenone (1450-74-4)

Conditions	Yield
With aluminium trichloride at 180℃; for 0.5h;	70%
With iron(III) chloride
Stage #1: 4-chloro-phenol; acetyl chloride In toluene at 40℃; Stage #2: With aluminium trichloride In toluene at 80℃; Further stages.;

Upstream product

• 64-19-7 acetic acid 
• 106-48-9 4-chloro-phenol 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 623-12-1 4-chloromethoxybenzene 
• 75-36-5 acetyl chloride 
• 118-93-4 o-hydroxyacetophenone 
• 108-24-7 acetic anhydride 
• 99-02-5 3'-Chloroacetophenone 
• 186956-36-5 1-(2-(allyloxy)-5-chlorophenyl)ethan-1-one 
• 55877-79-7 2-methoxy-5-chlorobenzonitrile 
• 6342-64-9 2-methoxy-5-chloroacetophenone 
• 876-27-7 4-chlorophenyl acetate 
• 861349-33-9 1-(5-chloro-2-methoxy-phenyl)-butane-1,3-dione 

Downstream Products

• 71354-54-6 3-acetyl-6-chloro-2-methyl-chromen-4-one 
• 91552-13-5 1-(2-acetoxy-5-chloro-phenyl)-ethanone 
• 129333-67-1 Phenyl-acetic acid 2-acetyl-4-chloro-phenyl ester 
• 150986-67-7 2-acetyl-4-chlorophenyl trifluoromethanesulfonate 
• 5067-25-4 1-(2-hydroxy-5-chlorophenyl)-3-phenylpropane-1,3-dione 
• 128671-35-2 5-chloro-(p-methoxy)cinnamoyloxyacetophenone 
• 145665-67-4 4-Acetylamino-3-nitro-benzoic acid 2-acetyl-4-chloro-phenyl ester 
• 146517-63-7 (E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(4-chloro-naphthalen-1-yl)-propenone 
• 147722-95-0 (E)-3-(6-Bromo-4H-benzo[1,3]dioxin-8-yl)-1-(5-chloro-2-hydroxy-phenyl)-propenone 
• 88-87-9 4-chloro-2,6-dinitrophenol 
• 84942-40-5 5′‐chloro‐2′‐hydroxy‐3′‐nitroacetophenone 
• 132314-52-4 5-chloro-3-nitro-2-nitratoacetophenone 
• 127767-22-0 3-Nitro-benzoic acid 2-acetyl-4-chloro-phenyl ester 
• 15934-73-3 2,2'-Dihydroxy-3,5-dibrom-5'-chlor-chalkon 

Relevant articles and documents

Chromone dioxadiazole compound as well as preparation method and application thereof

The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

Synthesis and Antibacterial Screening of Some New Pyrazolylchromones and Pyrazolylcoumaran-3-ones

Some new pyrazolylchromones 4a-e (flavone analogs) and pyrazolylcoumaran-3-ones 5a-e (aurone analogs) were synthesized by refluxing chalcones 3a-e in dimethyl sulfoxide/I2 and Pyridine/ Hg(OAc)2, respectively. Spectral techniques such as infrared, proton nuclear magnetic resonance, and mass spectrometry were used to confirm the structures of newly synthesized compounds. These compounds were studied for their antibacterial activities toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi. Some of these compounds showed promising activity against test organisms.