99-93-4

Basic information

• Product Name: 4'-Hydroxyacetophenone
• Synonyms: 1-(4-hydroxyphenyl)-ethanon;4’-hydroxy-acetophenon;4-Hydroksyacetofenol;Acetophenone, p-hydroxy-;Ethanone, 1-(4-hydroxyphenyl)-;Hydroxyacetophenone, para;Methyl p-hydroxyphenyl ketone;methyl-p-hydroxyphenylketone
• CAS NO: 99-93-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 202-802-8
• Product Categories: Acetophenone Series;FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);Carbonyl Compounds;AcetophenoneCarbonyl Compounds;C7 to C8;Ketones;Organic Photoinitiators;Polymerization Initiators;Aromatics;Miscellaneous Reagents;Pharmaceutical intermediates for Choleretic and Salbutamol;Eczema, medicine and other organic synthesis intermediates;Pyridines
• Mol File: 99-93-4.mol
• Article Data: 426

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Boiling Point: 147-148 °C3 mm Hg(lit.)
• Flash Point: 166 °C
• Appearance: Almost white to beige/Crystalline Powder
• Density: 1.109
• Vapor Pressure: 0.002Pa at 20℃
• Refractive Index: 1.5577 (estimate)
• Storage Temp.: Refrigerator
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 8.05(at 25℃)
• Water Solubility: 10 g/L (22 ºC)
• BRN: 774355
• CAS DataBase Reference: 4'-Hydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Hydroxyacetophenone(99-93-4)
• EPA Substance Registry System: 4'-Hydroxyacetophenone(99-93-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36/37-37/39-24/25-22-36
• WGK Germany: 3
• RTECS: PC4959775
• TSCA: Yes
• Hazardous Substances Data: 99-93-4(Hazardous Substances Data)

Usage

Chemical Properties

White to beige powder; sweet, hawthorn, balsam, mimosa aroma

Occurrence

Reported found in cloudberry, coffee, cranberry, mango, sherry, and wort.

Uses

Different sources of media describe the Uses of 99-93-4 differently. You can refer to the following data:
1. 4?-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
2. 4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
3. p-Hydroxyacetophenone is widely used in medicine, cosmetics and industrial fields. It is a natural plant extract, which naturally exists in the stems and leaves of the Compositae plant, Artemisia annua, the roots of plants such as Artemisia annua, Rhododendron, and Panax ginseng. It has a good effect on yellow eyes caused by diseases such as hepatitis, and also has a good auxiliary effect on yellow eyes caused by various reasons. Due to its weak molecular activity, high temperature resistance, melting point of 95-97 °C and boiling point of 296 °C, it is widely used in various liquid pharmaceuticals and can prolong the shelf life of other active ingredients under high temperature conditions. It has no harm to human skin and is the safest high-temperature auxiliary active stabilizer in the pharmaceutical industry.

Preparation

Preparation by Fries rearrangement of phenyl acetate with Lewis acidsaluminium chloridein nitrobenzene at 20–25° or at 50–60°in chlorobenzene between 45° and 65°, sealed tube and subjected to high power microwave irradiation for 2 min only (36%) in nitroethane at 60° (44%)in carbon disulfide at 45° (40%)in petroleum ether at 50° (20%) but between 130° and 175° (40–60%)aluminium chloride–sodium chloride mixture at 240–250° (10%) boron trifluoride at 90° (56%) scandium tris(trifluoromethanesulfonate), in nitromethane, at 50° (39%)titanium tetrachloride at 90–100° (34%)ferric chloride at 65° (25%)zinc chloride at 125° (8%) hydrofluoric acid, between 20° and 100° (94%) polyphosphoric acid, between 20° and 100° (69%) (50–53%)(44%)Nafion-XR 500, sulfonic acid type at 100°ZSM-5, in sulfolane, at 180° (28%)H-ZSM-5 at 400° or at 210° (6%) H-Nu-2 at 170° (15%)HY (Si/Al = 3) or fluorided alumina (Al2O3-F; 3 % wt. F), at 400°.

Definition

ChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.

Aroma threshold values

Floral type, medium strength odor; recommend smelling in a 10.00% solution or less.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 5829, 1991 DOI: 10.1016/S0040-4039(00)93567-6

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.]

Synthetic route

4-(tert-butyldimethylsilyloxy)acetophenone (149683-53-4) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With water; potassium carbonate In ethanol at 75℃; for 16h;	100%
With water; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.0166667h; chemoselective reaction;	97%
With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 16h;	96%

1-(4-(allyloxy)phenyl)ethanone (2079-53-0) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;	100%
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 1h;	99%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 20℃; for 4h; Inert atmosphere;	93%

2-methyl-2-(4-hydroxyphenyl)-1,3-dithiane (155853-28-4) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 1h;	100%
With dihydrogen peroxide; tantalum pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 1h;	100%
With iron(III)-acetylacetonate; dihydrogen peroxide; sodium iodide In water; ethyl acetate at 20℃; for 0.3h;	90%
With Amberlite IR-120; palladium on activated charcoal In methanol for 8h; Heating;	88%
With β‐cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetone at 20℃; for 2.5h;	85%

4-Iodoacetophenone (13329-40-3) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With sodium hydroxide; copper(l) iodide; L-proline In water at 20 - 300℃; microwave irradiation;	100%
Stage #1: 4-Iodoacetophenone With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	96%
With copper(l) iodide; potassium hydroxide In water at 100℃; Inert atmosphere;	96%

C20H18O3 → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In aq. phosphate buffer; dichloromethane at 0 - 20℃; for 22.5h; pH=7;	100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In aq. phosphate buffer; dichloromethane at 0 - 20℃; for 22.5h;	100%

4’-benzenesulfoxyacetophenone (64101-66-2) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;	100%

4-hydroxyacetophenone semicarbazone (22107-31-9) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With hydrogenchloride; Tonsil In ethyl acetate for 1.5h; Heating;	99.5%
With copper dichloride In acetonitrile for 0.5h; Heating;	98%
With ammonium persulfate; montmorrilonite K10 clay In solid for 1h; Irradiation; ultrasound irradiation;	94%

1-(4-hydroxyphenyl)ethanol (93453-79-3) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	99.3%
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 0.5h;	96%
With N-Bromosuccinimide; β‐cyclodextrin In methanol; water; acetone at 20℃; for 10h;	95%

acetyl chloride (75-36-5) + phenol (108-95-2) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With trifluorormethanesulfonic acid at 0 - 20℃; for 1h; Friedel-Crafts acylation; regiospecific reaction;	99%
With iron(III) chloride; lithium chloride In 1,2-dichloro-benzene at 70℃; for 5h; Reagent/catalyst; Temperature;	90%
Stage #1: phenol With aluminum (III) chloride In dichloromethane for 1h; Friedel Crafts acylation; Stage #2: acetyl chloride In dichloromethane for 14h; Friedel Crafts acylation;	73.5%

4'-benzyloxy-acetophenone (54696-05-8) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With cyclohexa-1,4-diene; polymer-CH2NMe3Cl; palladium In ethanol at 55℃; for 1.5h;	99%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 1h; Inert atmosphere;	99%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;	99%

potassium 4-acetylphenyltrifluoroborate → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With Oxone; water In acetone at 20℃; for 0.0333333h;	99%
With cyclohexanone monooxygenase from Acinetobacter sp.; phosphite dehydrogenase; NADPH In dimethyl sulfoxide at 24℃; for 24h; Tris/HCl buffer; Enzymatic reaction; chemoselective reaction;

4'-ethoxyacetophenone (1676-63-7) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;	99%

<4-Acetyl-phenyl>-tritylether (96179-09-8) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With Aliquat 336; sodium carbonate; benzaldehyde In water at 70℃; for 10h; Reagent/catalyst; Time; Aldol Condensation;	99%

1-(4-(2-hydroxyethoxy)phenyl)ethanone (31769-45-6) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;	99%

N-[2-(4-hydroxyphenyl)-2-oxoethyl]phenylalanine hydrochloride methyl ester → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
In aq. phosphate buffer pH=5.6; Irradiation;	99%

para-chloroacetophenone (99-91-2) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With [(2-di-tert-butylphosphino-3-methoxy-6-methyl-2,4,6-triisopropyl-1,1-biphenyl)-2-(2-aminobiphenyl)]palladium(II) methanesulfonate; caesium carbonate; Benzaldoxime In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;	98%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;	98%
With sodium hydroxide at 165℃; for 5h; Temperature; Reagent/catalyst;	97%

4-acetyloxyacetophenone (13031-43-1) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With indium(III) chloride; ammonium chloride; aluminium In ethanol; water at 80℃; for 11h;	98%
With ammonium acetate In methanol at 20℃; for 3.5h;	95%
With amberlyst-15 In methanol at 20℃; for 2.5h;	95%

1-(4-methoxyphenyl)ethanone (100-06-1) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 220℃; for 0.666667h; Inert atmosphere; Microwave irradiation;	98%
With 1-butylpyridinium bromide at 100℃; Microwave irradiation; Neat (no solvent);	94%
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one for 0.25h; Heating;	90%

4-benzoyloxyacetophenone (1523-18-8) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one at 100℃; for 1h;	98%
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;	90%
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Hydrolysis; debenzoylation; Heating;	85%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;	73%

4-acetylphenylboronic acid (149104-90-5) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With menadione; sodium hydrogencarbonate; sodium L-ascorbate In ethanol; water at 20℃; under 760.051 Torr; for 24h; pH=8.5; Darkness; Green chemistry;	98%
With tert.-butylhydroperoxide; potassium hydroxide In water at 20℃; for 0.166667h;	97%
With water; dihydrogen peroxide at 20℃; for 0.133333h; Green chemistry;	97%

para-bromoacetophenone (99-90-1) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;	98%
Stage #1: para-bromoacetophenone With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 90℃; for 21h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;	96%
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;	95%

2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-phenoxy]-tetrahydro-pyran → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With Ru(CH3CN)3(triphos)(OTf)2 (triphos = CH3C(CH2PPh2)3); acetone for 5h; Ambient temperature;	97%

1-(4-((4-nitrobenzyl)oxy)phenyl)ethanone → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With indium; ammonium chloride In ethanol for 18h; Debenzylation; Heating;	97%
With indium; ammonium chloride In methanol for 18h; Heating;	97%

methoxybenzene (100-66-3) + acetyl chloride (75-36-5) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
Stage #1: methoxybenzene; acetyl chloride With aluminum (III) chloride; 1,2-dichloro-benzene at 5 - 10℃; for 3h; Stage #2: With ethane-1,2-dithiol at 35 - 40℃; for 2h; Stage #3: With hydrogenchloride at 25 - 100℃; pH=1 - 2; Cooling with ice;	97%
With ytterbium(III) triflate In carbon disulfide for 6h; Friedel-Crafts reaction; Heating;	75%

dihydrogen peroxide (7722-84-1) + 4-acetylphenylboronic acid (149104-90-5) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;	97%

1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol (106534-23-0) → 2-methoxy-phenol (90-05-1) + 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 4h;	A n/a B 97%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;	A 90% B 76%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;	A 90% B 76%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;

(E)-1-(4-hydroxyphenyl)ethan-1-one oxime (198712-64-0) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With manganese triacetate In benzene for 2h; Heating;	96%
With zeolyte H-Y supported KMnO4 In 1,2-dichloro-ethane for 0.5h; Ambient temperature;	83%

4-hydroxyacetophenone oxime (34523-34-7) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 0.0166667h; neat (no solvent);	96%
With water; dihydrogen peroxide; iodine In acetonitrile at 20℃; for 12h;	92%
With formic acid; silica gel for 0.05h; microwave irradiation;	91%

4-Hydroxyacetophenone N,N-dimethylhydrazone (5757-91-5) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.0833333h; Hydrolysis;	96%

phenol (108-95-2) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With potassium hydroxide; hydrogen fluoride; acetic acid In ethyl acetate	96%
Multi-step reaction with 2 steps 1: acetic acid anhydride; concentrated H2SO4 2: AlCl3; carbon disulfide View Scheme
Multi-step reaction with 2 steps 1: acetic acid anhydride; concentrated H2SO4 2: AlCl3 / 175 °C View Scheme

benzaldehyde (100-52-7) + 4-Hydroxyacetophenone (99-93-4) → (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one (2657-25-2)

Conditions	Yield
With potassium hydroxide In ethanol; water at 0 - 20℃; for 24h;	100%
With cesium 12-tungstophosphate at 50℃; for 0.5h; Time; Claisen-Schmidt Condensation; Green chemistry; Further stages;	98%
In neat (no solvent) at 50℃; for 0.416667h; Claisen-Schmidt Condensation; Milling; Green chemistry; chemoselective reaction;	95%

allyl bromide (106-95-6) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-(allyloxy)phenyl)ethanone (2079-53-0)

Conditions	Yield
With potassium carbonate In acetone at 20℃; Reflux;	100%
With potassium carbonate In acetone Inert atmosphere; Reflux;	100%
With potassium carbonate In acetonitrile at 60℃; for 6h;	99%

Cyclopentyl bromide (137-43-9) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-cyclopentyloxy-phenyl)-ethanone (857563-36-1)

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 3h;	100%
With sodium hydroxide

1-Bromopentane (110-53-2) + 4-Hydroxyacetophenone (99-93-4) → 4-pentyloxyacetophenone (5467-56-1)

Conditions	Yield
With potassium carbonate In water; ethyl acetate; acetone	100%
With potassium carbonate In N,N-dimethyl-formamide for 16h; Reflux;	92%
With potassium carbonate; potassium iodide In acetone Inert atmosphere; Reflux;	78%

4-Hydroxyacetophenone (99-93-4) → 4'-hydroxy-3'-nitroacetophenone (6322-56-1)

Conditions	Yield
With copper nitrate - dinitrogen tetroxide adduct In acetone for 0.0833333h; Heating;	100%
With trichloroisocyanuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.333333h;	97%
With poly(ethylene glycol)-N2O4 In dichloromethane at 20℃; for 0.333333h;	95%

4-Hydroxyacetophenone (99-93-4) → 1-(4-hydroxyphenyl)ethanol (93453-79-3)

Conditions	Yield
Stage #1: 4-Hydroxyacetophenone With sodium tetrahydroborate at 60℃; for 1h; Ball milling; neat (no solvent); Stage #2: With water regiospecific reaction;	100%
With sodium tetrahydroborate In ethanol for 5h;	99.6%
With sodium isopropylate; acetonitrile In isopropyl alcohol at 80℃; for 5h; Catalytic behavior;	99%

4-Hydroxyacetophenone (99-93-4) → 4-hydroxyacetophenone oxime (34523-34-7)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;	100%
With hydroxylamine hydrochloride; sodium acetate In water for 1h; Heating;	98%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;	91%

Hexanoyl chloride (142-61-0) + 4-Hydroxyacetophenone (99-93-4) → p-Acetoxyphenylhexanoat (68437-46-7)

Conditions	Yield
Stage #1: 4-Hydroxyacetophenone With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 0.0333333h; Stage #2: Hexanoyl chloride In tetrahydrofuran for 0.25h;	100%
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In dichloromethane for 1.5h; Ambient temperature;	89%
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In dichloromethane for 2.33333h; Ambient temperature;	84%
With pyridine In benzene

3,4-dihydro-2H-pyran (110-87-2) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone (16162-69-9)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane for 1.5h; Ambient temperature;	100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;	95%
Stage #1: 4-Hydroxyacetophenone With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 0.5h; Stage #2: 3,4-dihydro-2H-pyran In dichloromethane at 20℃; for 4h;	95%

benzyl bromide (100-39-0) + 4-Hydroxyacetophenone (99-93-4) → 4'-benzyloxy-acetophenone (54696-05-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 20℃; for 17h;	100%
Stage #1: 4-Hydroxyacetophenone With potassium carbonate In acetone at 20℃; Inert atmosphere; Stage #2: benzyl bromide In acetone for 12h; Reflux; Inert atmosphere;	100%
Stage #1: 4-Hydroxyacetophenone With potassium carbonate In acetone at 20℃; for 1h; Stage #2: benzyl bromide In acetone for 12h; Reflux;	100%

1,3-chlorobromopropane (109-70-6) + 4-Hydroxyacetophenone (99-93-4) → 1-[4-(3-chloropropoxy)phenyl]ethanone (91427-23-5)

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 18h;	100%
With potassium carbonate In acetone at 65℃;	99%
With potassium carbonate In acetone at 65℃;	99%

propargyl bromide (106-96-7) + 4-Hydroxyacetophenone (99-93-4) → 4-(2-propynyloxy)acetophenone (34264-14-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 25℃; for 24h;	100%
With potassium carbonate In acetone Reflux;	100%
Stage #1: 4-Hydroxyacetophenone With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: propargyl bromide With potassium carbonate In toluene at 50℃; for 2h; Inert atmosphere;	96%

3-chloro-3-methylbut-1-yne (1111-97-3) + 4-Hydroxyacetophenone (99-93-4) → 4-(1,1-dimethylprop-2-ynyloxy)acetophenone (35816-87-6)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃;	100%
With copper(l) iodide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃;	85%
With potassium carbonate In acetone for 18h; Reflux;	81%

1-bromo-5-chloropentane (54512-75-3) + 4-Hydroxyacetophenone (99-93-4) → 4-chloropentoxyacetophenone (61523-83-9)

Conditions	Yield
	100%
With potassium carbonate In acetone
With potassium hydroxide In methanol for 24h; Heating;

trifluoromethylsulfonic anhydride (358-23-6) + 4-Hydroxyacetophenone (99-93-4) → 4-acetophenyl triflate (109613-00-5)

Conditions	Yield
With triethylamine at -40℃; for 0.25h;	100%
With pyridine In dichloromethane at -15℃; for 1h;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	95%

2-Methoxyethoxymethyl chloride (3970-21-6) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-((2-methoxyethoxy)methoxy)phenyl)ethanone (84775-31-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h;	100%
With potassium carbonate In acetone for 1h; Heating;

4-Hydroxyacetophenone (99-93-4) + methyl iodide (74-88-4) → 1-(4-methoxyphenyl)ethanone (100-06-1)

Conditions	Yield
With potassium carbonate In acetone Heating;	100%
With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 25℃; for 2h; Williamson synthesis;	99%
With potassium carbonate In acetone Heating;	98%

4-Hydroxyacetophenone (99-93-4) → 4-acetaminophenol (103-90-2)

Conditions	Yield
With hydroxylamine hydrochloride In acetonitrile at 110℃; for 1h; Solvent; Time; chemoselective reaction;	100%
With hydroxylamine hydrochloride; tetrachlorosilane at 160℃; for 0.0583333h; microwave irradiation;	92%
With mesitylenesulfonylhydroxylamine In acetonitrile at 20℃; for 6h;	92%

4-Hydroxyacetophenone (99-93-4) → sodium 4-acetylphenolate (3019-86-1)

Conditions	Yield
With sodium hydride In benzene for 0.5h;	100%

triisopropylsilyl chloride (13154-24-0) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-((triisopropylsilyl)oxy)phenyl)ethanone (935859-12-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide for 3h;
With 1H-imidazole In tetrahydrofuran at 35℃; for 20h;

tert-butyldimethylsilyl chloride (18162-48-6) + 4-Hydroxyacetophenone (99-93-4) → 4-(tert-butyldimethylsilyloxy)acetophenone (149683-53-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;	100%
With P(MeNCH2CH2)3N; triethylamine In acetonitrile at 24℃; for 2h;	99%

1,3,5-Tris(bromomethyl)benzene (18226-42-1) + 4-Hydroxyacetophenone (99-93-4) → 1-{4-[3,5-di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (199865-07-1)

Conditions	Yield
With Aliquat 336; potassium carbonate; potassium iodide In acetone for 48h; Heating;	100%
With Aliquat 336; potassium carbonate; potassium iodide In acetone for 48h; Heating;	95%

p-toluenesulfonyl chloride (98-59-9) + 4-Hydroxyacetophenone (99-93-4) → 4-acetylphenyl p-toluenesulfonate (64101-67-3)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;	100%
With triethylamine; dmap In dichloromethane for 2h;	100%
With triethylamine In dichloromethane at 20℃; for 3h;	98%

tert-butylchlorodiphenylsilane (58479-61-1) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-((tertbutyldiphenylsilyl)oxy)phenyl)ethan-1-one (845504-46-3)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
Stage #1: 4-Hydroxyacetophenone With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 20℃; Inert atmosphere;
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 24h; Inert atmosphere;

polymer, 1.6 mmol/g NTf2 units; monomer(s): styrene; 1,4-bis(4-vinylphenoxy)butane; N-(4-vinylphenyl)trifluoromethanesulfonimide + 4-Hydroxyacetophenone (99-93-4) → 4-acetophenyl triflate (109613-00-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%

4-Hydroxyacetophenone (99-93-4) + Benzyl bromoacetate (5437-45-6) → benzyl 2-(4-acetylphenoxy)acetate (851875-31-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Williamson ether synthesis;	100%
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 1.5h;	79.8%

Upstream product

• 71-55-6 1,1,1-trichloroethane 
• 139-02-6 sodium phenoxide 
• 13110-96-8 5-acetylsalicylic acid 
• 141-78-6 ethyl acetate 
• 108-95-2 phenol 
• 88-69-7 2-(1-methylethyl)phenol 
• 75-36-5 acetyl chloride 
• 123-75-1 pyrrolidine 
• 13031-43-1 4-acetyloxyacetophenone 
• 123-07-9 4-Ethylphenol 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 110-82-7 cyclohexane 
• 114691-94-0 (4-acetylphenoxy)carbonyl azide 
• 54696-05-8 4'-benzyloxy-acetophenone 

Downstream Products

• 2079-51-8 1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)ethanone 
• 5424-02-2 (E)-1-(4-hydroxyphenyl)-3-(2-chlorophenyl)prop-2-en-1-one 
• 97355-91-4 (2E)-1-(4-hydroxyphenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one 
• 54696-05-8 4'-benzyloxy-acetophenone 
• 6338-81-4 4'-hydroxy-4-methoxychalcone 
• 82522-52-9 (E)-3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-2-propen-1-one 
• 1523-18-8 4-benzoyloxyacetophenone 
• 14733-22-3 1-(4-(2-(diethylamino)ethoxy)phenyl)ethan-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 84380-07-4 (4-acetyl-phenyl)-(tetra-O-acetyl-α-D-galactopyranoside) 
• 56220-22-5 1-[4-(2-Hydroxy-butoxy)-phenyl]-ethanone 
• 29816-95-3 p-Acetylphenyl-acetoacetat 
• 38528-20-0 Thiophosphoric acid O-(4-acetyl-phenyl) ester O'-ethyl ester S-propyl ester 
• 68432-05-3 4-(3-amino-4,5-dihydro-isoxazol-5-yl)-phenol 

Relevant articles and documents

-

-

-

-

Development of pH-activatable fluorescent probes for rapid visualization of metastatic tumours and fluorescence-guided surgeryviatopical spraying

A series of pH-activatable aza-BODIPY-based fluorescent probes were developed for rapid cancer visualization and real-time fluorescence-guided surgery by harnessing topical spraying. These probes exhibited good water-solubility, a tunable pKafrom 5.0 to 7.9, and stable intense NIR emission at ～725 nm under acidic conditions.AzaB5with a pKavalue of 6.7 was able to rapidly and clearly visualize pulmonary and abdominal metastatic tumours including tiny metastases less than 2 mmviatopical spraying, further improving intraoperative fluorescence-guided resection. We believe thatAzaB5is promising as a powerful tool to rapidly delineate a broad range of malignancies and assist surgical tumour resection.

A copper nitride catalyst for the efficient hydroxylation of aryl halides under ligand-free conditions

Copper nitride (Cu3N) was used as a heterogeneous catalyst for the hydroxylation of aryl halides under ligand-free conditions. The cubic Cu3N nanoparticles showed high catalytic activity, comparable to those of conventional Cu catalysts with nitrogen ligands, demonstrating that the nitrogen atoms in Cu3N act as functional ligands that promote hydroxylation.