3-hydroxy phenylacetylene
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation; | 100% |
With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 1h; Catalytic behavior; Temperature; Microwave irradiation; Inert atmosphere; | 92% |
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25℃; for 24h; Sealed tube; regioselective reaction; | 87% |
With water at 60℃; for 20h; Sealed tube; | 63% |
With methanesulfonic acid; iron(II) chloride tetrahydrate In 1,2-dichloro-ethane at 60℃; for 2h; Inert atmosphere; | 49% |
1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 7h; Inert atmosphere; | 99% |
With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 16h; | 88% |
With KF-Al2O3 (acidic) In acetonitrile for 48h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 80℃; for 14h; | 96% |
With bis(η3-allyl-μ-chloropalladium(II)); t-BuBrettPhos; p-methylbenzaldehyde oxime; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; | 90% |
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 88% |
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; | 72% |
1-(3-ethoxyphenyl)ethan-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With water; sodium acetate In ethanol for 5h; Reflux; | 98% |
With potassium hydrogensulfate; silica gel In methanol at 20℃; for 1h; | 94% |
With sodium hydroxide |
3'-iodoacetophenone
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 98% |
With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; | 95% |
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 6h; Sealed tube; Inert atmosphere; | 90% |
3-acetyl phenyltrifluoromethanesulfonate
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 1h; | 97% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere; | 97% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With water; caesium carbonate; hydrazine hydrate at 80℃; for 48h; | 95% |
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry; | 68% |
With recombinant phenylacetone monooxygenase from Thermobifida fusca, M446G mutant; NADPH In dimethyl sulfoxide at 25℃; pH=9; Kinetics; Tris/HCl buffer; Enzymatic reaction; chemoselective reaction; | |
Multi-step reaction with 2 steps 1: tetrahydrofuran / 40 °C / Reduced pressure 2: recombinant phenylacetone monooxygenase from Thermobifida fusca; NADPH / dimethyl sulfoxide / 25 °C / pH 9 / Tris/HCl buffer; Enzymatic reaction View Scheme | |
With oxygen; N-ethyl-N,N-diisopropylamine; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 12h; Irradiation; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 95% |
methyllithium
3-Carboxyphenol
A
3-Hydroxyacetophenone
B
meta-hydroxy-α,α-dimethylbenzyl alcohol
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at 0℃; for 2h; Yields of byproduct given; | A 94% B n/a |
With chloro-trimethyl-silane In tetrahydrofuran; diethyl ether at 0℃; for 2h; Yield given; | A 94% B n/a |
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide at 220℃; for 0.666667h; Inert atmosphere; Microwave irradiation; | 92% |
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h; | 83% |
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux; | 76% |
With sodium thioethylate In N,N-dimethyl-formamide at 80℃; for 3.5h; | 18% |
1-(3-(methoxymethoxy)phenyl)ethan-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 0℃; for 0.0333333h; | 92% |
acetic acid 3-aminophenyl ester
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
Stage #1: acetic acid 3-aminophenyl ester With sulfuric acid at 20℃; Cooling with ice; Stage #2: With sodium nitrite In water Reflux; | 92% |
1-(3-(allyloxy)phenyl)ethanone
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating; | 90% |
1-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 0℃; for 0.0333333h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 1-(3-aminophenyl)ethanone With sulfuric acid In water at 45 - 50℃; for 0.5h; Stage #2: With water; urea; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene; water at 90℃; for 2h; | 88.3% |
Stage #1: 1-(3-aminophenyl)ethanone With sodium nitrite In water at 20℃; Milling; Green chemistry; Stage #2: With water at 80℃; for 0.5h; Neutral conditions; Green chemistry; | 80% |
With uranyl nitrate hydrate; water; trifluoroacetic acid for 48h; Irradiation; Inert atmosphere; | 58% |
With sulfuric acid; water Diazotization; |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With water In dimethyl sulfoxide at 155℃; for 0.5h; | 85% |
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Concentration; Schlenk technique; Inert atmosphere; | 82% |
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation; | 81% |
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 54% |
1-[3-(phenylmethoxy)phenyl]ethan-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel; methoxybenzene at 115℃; for 3h; | 81% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With acetic acid In water at 90℃; for 4h; Reagent/catalyst; Temperature; | 77.6% |
3-acetyl-2-cyclohexen-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); 6,6'-dimethyl-2,2'-bipyridine; sodium anthraquinone-2-sulfonate; oxygen In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 24h; | 77% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With potassium fluoride; dihydrogen peroxide; sodium hydrogencarbonate In tetrahydrofuran; methanol at 40℃; | 76% |
5-acetyl-2-cyclohexen-1-one
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With lithium bromide; copper(ll) bromide In acetonitrile for 1h; Heating; | 75% |
tert-Butyl acrylate
4-iodoanisol
1-(3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethanone
A
3-Hydroxyacetophenone
B
1,1'-(biphenyl-3,3'-diyl)bis(ethan-1-one)
C
tert-butyl (E)-3-(2-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; Further byproducts given; | A 6% B 5% C 26% D 71% |
3-hydroxy phenylacetylene
acetic acid
A
3-Hydroxyacetophenone
B
3-acetylphenyl acetate
Conditions | Yield |
---|---|
With iron(III) sulfate hydrate at 95℃; for 24h; Schlenk technique; | A 71% B 6% |
Conditions | Yield |
---|---|
With iodine; hydrazine hydrate; dimethyl sulfoxide In water; acetonitrile at 80℃; for 7.5h; | 64.7% |
With chromium(VI) oxide |
Conditions | Yield |
---|---|
With Candida albicans CCT 0776 In water at 30℃; for 144h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 42% B 42% |
With immobilized Candida albicans CCT 0776 cells in calcium alginate beads In water at 30℃; for 16h; Reagent/catalyst; | A n/a B n/a |
acetophenone
A
3-Hydroxyacetophenone
B
o-hydroxyacetophenone
C
4-Hydroxyacetophenone
Conditions | Yield |
---|---|
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation; Green chemistry; | A 6% B 38% C 14% |
With hydroxyl radical; potassium hexacyanoferrate(III) Rate constant; Ambient temperature; also without K3Fe(CN)6; | |
With air; carbon monoxide; sodium acetate; palladium on activated charcoal; phosphovanadomolybdic acid In water; acetic acid at 120℃; under 15200 Torr; for 4h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
With NaH In N,N-dimethyl-formamide | 98% |
With sodium ethanolate |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; Reflux; | 100% |
With potassium carbonate In acetone for 8h; Heating; | 95% |
With potassium carbonate In ethanol for 3h; Reflux; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxyacetophenone With sodium tetrahydroborate at 60℃; for 0.5h; Ball milling; neat (no solvent); Stage #2: With water regiospecific reaction; | 100% |
With formic acid; C18H24ClIrN3 In water at 80℃; for 4h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 99% |
With sodium tetrahydroborate; nickel(II) phthalocyanine In PEG-400 at 20℃; for 0.416667h; chemoselective reaction; | 86% |
Conditions | Yield |
---|---|
With sodium hydride In benzene for 0.5h; | 100% |
3-Hydroxyacetophenone
benzyl bromide
1-[3-(phenylmethoxy)phenyl]ethan-1-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; Inert atmosphere; | 100% |
With potassium carbonate; potassium iodide In acetone for 24h; Heating / reflux; | 98% |
In N,N-dimethyl-formamide; mineral oil | 97% |
3-Hydroxyacetophenone
3,4-dimethoxy-benzaldehyde
(E)-1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 0 - 20℃; for 16h; | 100% |
With potassium hydroxide In ethanol; water at 0 - 20℃; | 92% |
With potassium hydroxide In ethanol at 20℃; for 16h; Condensation; | 91% |
Conditions | Yield |
---|---|
With sodium ethanolate In tetrahydrofuran at 25℃; for 0.00277778h; microwave irradiation; | 100% |
With potassium tert-butylate In tetrahydrofuran at 20℃; Claisen Condensation; | 88% |
3-Hydroxyacetophenone
tert-butyldimethylsilyl chloride
1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h; | 93% |
With dmap; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 2.5h; | 91% |
N-ethyl-N-methylcarbamoyl chloride
3-Hydroxyacetophenone
1-(N-ethyl-N-methylaminocarbonyloxy)-3-acetylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20 - 55℃; for 5h; Product distribution / selectivity; Heating / reflux; | 100% |
With potassium carbonate In acetone for 4h; Reflux; | 100% |
With potassium carbonate In acetone at 60℃; for 0.4h; Reagent/catalyst; Temperature; Solvent; | 100% |
3-Hydroxyacetophenone
3-Chloro-2-methylpropene
1-[3-(2-methylallyloxy)phenyl]ethanone
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; | 100% |
With potassium carbonate In acetonitrile for 17h; Reflux; |
3-Hydroxyacetophenone
propargyl bromide
1-(3-(prop-2-yn-1-yloxy)phenyl)ethan-1-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 25℃; for 24h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | |
Stage #1: 3-Hydroxyacetophenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 0 - 25℃; for 16h; |
Conditions | Yield |
---|---|
With iodine at 140℃; for 3h; | 100% |
With iodine at 140℃; for 3h; | 100% |
With iodine at 140℃; for 3h; | 100% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With C38H46ClIrN2P; hydrogen; sodium t-butanolate In ethanol at 0 - 50℃; under 1500.15 - 75007.5 Torr; Reagent/catalyst; Solvent; Inert atmosphere; Autoclave; | 100% |
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction; | 99% |
With formic acid; triethylamine; [Ru(η6-p-cymene)(HNC(Ph)C(Ph)NTs)] In ethanol at 60 - 70℃; for 5h; Product distribution / selectivity; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
Stage #1: 3-Hydroxyacetophenone With potassium carbonate In acetone for 0.166667h; Stage #2: dimethyl sulfate In acetone at 45℃; for 2h; | 99.73% |
With potassium carbonate In acetone at 45℃; for 2h; Large scale reaction; | 95% |
Stage #1: 3-Hydroxyacetophenone With sodium hydroxide In water for 0.5h; Large scale; Stage #2: dimethyl sulfate In water at 30 - 38℃; for 9.15h; pH=> 13; Temperature; pH-value; Microwave irradiation; Large scale; | 91.1% |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 20℃; for 1h; | 99% |
With sodium hydroxide In water at 0℃; for 1.5h; pH=7 - 8; | 94% |
copper(II) bis(tetrafluoroborate) at 20℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 4h; Inert atmosphere; | 99% |
trifluoromethylsulfonic anhydride
3-Hydroxyacetophenone
3-acetyl phenyltrifluoromethanesulfonate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; dmap In dichloromethane for 2h; Ambient temperature; | 99% |
With pyridine In dichloromethane at 0 - 20℃; | 96% |
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 1h; | 99% |
With zeolite HSZ-360 In toluene for 11h; Heating; | 88% |
With toluene-4-sulfonic acid In benzene Heating / reflux; | 36% |
3-Hydroxyacetophenone
p-toluenesulfonyl chloride
3-acetylphenyl p-toluenesulfonate
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry; | 99% |
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; Inert atmosphere; | 91% |
With dmap; triethylamine In dichloromethane |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 40℃; for 4.5h; | 99% |
n-propanesulfonyl chloride
3-Hydroxyacetophenone
3-acetylphenyl propane-1-sulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In dichloromethane at 50℃; for 3h; Reagent/catalyst; Time; Sealed tube; | 99% |
triisopropylsilyl chloride
3-Hydroxyacetophenone
1-(3-((triisopropylsilyl)oxy)phenyl)ethanone
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 6h; | 99% |
3-Hydroxyacetophenone
Conditions | Yield |
---|---|
With triethanolamine; N-benzyl-N,N,N-triethylammonium chloride; sodium iodide In acetone at 25℃; | 99% |
Conditions | Yield |
---|---|
With dmap In toluene at 130℃; for 1h; Microwave irradiation; Sealed tube; | 99% |
3-Hydroxyacetophenone
4-Hydrazino-5,6-tetramethylenethieno<2,3-d>pyrimidine
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 99% |
Molecular Structure of 3-Hydroxy acetophenone (CAS No.121-71-1):
Molecular Formula: C8H8O2
Molecular Weight: 136.15
IUPAC Name: 1-(3-Hydroxyphenyl)ethanone
CAS No: 121-71-1
EINECS: 204-494-0
Melting Point: 94-97 ºC
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.552
Molar Refractivity: 38.16 cm3
Molar Volume: 119.3 cm3
Surface Tension: 43.9 dyne/cm
Density: 1.14 g/cm3
Flash Point: 115.8 °C
Enthalpy of Vaporization: 53.62 kJ/mol
Boiling Point: 277 °C at 760 mmHg
Vapour Pressure: 0.00276 mmHg at 25°C
Canonical SMILES: CC(=O)C1=CC(=CC=C1)O
InChI: InChI=1S/C8H8O2/c1-6(9)7-3-2-4-8(10)5-7/h2-5,10H,1H3
InChIKey: LUJMEECXHPYQOF-UHFFFAOYSA-N
3-Hydroxy acetophenone (CAS No.121-71-1) is used for organic synthesis; as intermediate of Phenylephrine; synthesis of pharmaceutical intermediate .
Safety Information of 3-Hydroxy acetophenone (CAS No.121-71-1):
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26-36
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Harmful/Irritant
Assay of 3-Hydroxy acetophenone: 99%
3-Hydroxy acetophenone (CAS No.121-71-1), it also can be called m-Hydroxyacetophenone ; 3-Acetylphenol ; 1-(3-Hydroxyphenyl)ethanon ; Ethanone, 1- (3-hydroxyphenyl)- ; m-Acetylphenol ; 1-(3-Hydroxyphenyl)Ethan-1-One . It is beige-brown crystalline powder.
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