Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 0 - 20℃; for 1h; Friedel-Crafts acylation; regiospecific reaction; | 99% |
With aluminium trichloride In dichloromethane Friedel-Crafts acylation; | 53% |
man verseift das Propionat mit alkoh. Kalilauge; |
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Temperature; Microwave irradiation; | 94% |
Conditions | Yield |
---|---|
With hydrogen; nickel In isopropyl alcohol at 60℃; under 3102.9 Torr; 20-24 h; | 92% |
With trifluoroacetic acid |
4-{[(tert-butyl)(diphenyl)silyl]oxy}-3-methoxybenzaldehyde
1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)propan-1-one
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
Stage #1: 4-Methoxypropiophenone With 1-n-butyl-3-methylimidazolim bromide at 220℃; under 9000.9 Torr; for 0.666667h; Inert atmosphere; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride; water pH=1; | 90% |
With hydrogen bromide; acetic acid In water at 100℃; for 18h; Heating / reflux; | 70% |
With Pyridine hydrobromide at 240℃; for 0.25h; | 60% |
1-(4-(prop-2-yn-1-yloxy)phenyl)propan-1-one
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 28℃; for 19h; | 87% |
With Pd-catalyst In water; N,N-dimethyl-formamide |
4-hydroxy-α-ethylbenzylalcohol
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With C6H4MoNO7(1-)*C19H42N(1+); oxygen In water at 100℃; for 20h; Green chemistry; chemoselective reaction; | 81% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 0 - 20℃; for 4.5h; Inert atmosphere; | 80% |
With trifluorormethanesulfonic acid at 0 - 20℃; for 4.5h; | 80% |
With aluminium trichloride In nitrobenzene at 30℃; for 24h; Fries rearrangement; | 60% |
Conditions | Yield |
---|---|
Stage #1: propionic acid With trifluoromethylsulfonic anhydride at 20 - 60℃; Stage #2: phenol at 60℃; for 0.166667h; regiospecific reaction; | 80% |
With zinc(II) chloride | |
With boron trifluoride | |
With PPA |
4'-Bromopropiophenone
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With nickel(II) bromide trihydrate; water; 1-(2,2-diphenyl-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinolin-1(2H)-yl)-3-phenylpropan-1-one; N-ethyl-N,N-diisopropylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 25℃; for 22h; Irradiation; | 80% |
N,N-dimethyl-formamide
4-Hydroxyacetophenone
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube; | 73% |
phenyl propionate
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With aluminium trichloride In chlorobenzene at 106℃; under 760 Torr; for 0.05h; Irradiation; microwave oven; | A 28% B 62% |
With carbon disulfide; aluminium trichloride Erhitzen des Reaktionsgemisches auf 190grad; | |
With carbon disulfide; aluminium trichloride bei Siedetemperatur und anschliessend Abdestillieren des Schwefelkohlenstoffs und Erhitzen auf 140-150grad; | |
With aluminium trichloride; n-heptane Erhitzen des Reaktionsgemisches auf 190grad; |
phenyl propionate
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
C
phenol
Conditions | Yield |
---|---|
With β‐cyclodextrin In water at 25℃; for 1h; Product distribution; Quantum yield; Irradiation; various times, effect of oxygen, without cyclodextrin; | A 16.49% B 9.16% C n/a |
1-(2-Hydroxy-phenyl)-propan-1-on
A
phenyl propionate
B
2-chloro-1-(2-hydroxyphenyl)-1-propanone
C
4-hydroxypropiophenone
Conditions | Yield |
---|---|
iron(III) chloride at 170℃; for 24h; Mechanism; Product distribution; | A 8.7% B 5.9% C 0.7% |
diethyl ether
dibutyl ether
N, N-diethyl-4-hydroxybenzamide
ethylmagnesium bromide
4-hydroxypropiophenone
N, N-diethyl-4-hydroxybenzamide
ethylmagnesium bromide
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With diethyl ether; dibutyl ether Erhitzen des vom Diaethylaether befreiten Reaktionsgemisches auf Siedetemperatur und anschliessende Hydrolyse; |
4-t-amylphenol
propionic acid
A
1-(2-hydroxy-5-tert-pentyl-phenyl)-propan-1-one
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With boron trifluoride |
propionic acid
phenol
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With boron trifluoride Erwaermen des Reaktionsgemisches auf 75grad; | |
With boron trifluoride und Erwaermen des Reaktionsgemisches auf 75grad; |
Conditions | Yield |
---|---|
With N-butylamine In benzene for 0.4h; Ambient temperature; Yield given; |
4-propionylphenyl benzoate
N-butylamine
A
N-butylbenzamide
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
In benzene for 0.4h; Ambient temperature; Yields of byproduct given; |
1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)propan-1-one
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With potassium carbonate; [2.2.2]cryptande In acetonitrile at 55℃; for 2h; Yield given; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran |
boron trifluoride
propionic acid
phenol
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
at 73 - 75℃; | |
at 75℃; |
2-bromo-(4'-hydroxyphenyl)-propan-1-one
acetic acid
4-hydroxypropiophenone
carbon disulfide
aluminium trichloride
phenyl propionate
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
Erhitzen des vom Loesungsmittel befreiten Reaktionsgemisches auf 135-140grad; |
aluminium trichloride
n-heptane
phenyl propionate
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
at 80 - 90℃; Product distribution; |
aluminium trichloride
phenyl propionate
1,1,2,2-tetrachloroethane
A
1-(2-Hydroxy-phenyl)-propan-1-on
B
4-hydroxypropiophenone
Conditions | Yield |
---|---|
at 95℃; Product distribution; |
tetrachloromethane
bis-[1-(4-hydroxy-phenyl)-propylidene]-hydrazine
hydrogen bromide
4-hydroxypropiophenone
Conditions | Yield |
---|---|
in siedendem Xylol, nach laengerer Dauer; |
triisopropylsilyl chloride
4-hydroxypropiophenone
1-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)propan-1-one
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 14h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 3h; | 99% |
pivaloyl chloride
4-hydroxypropiophenone
p-(trimethylacetoxy)propiophenone
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 2h; | 100% |
Stage #1: 4-hydroxypropiophenone With sodium hydride In tetrahydrofuran; mineral oil Stage #2: pivaloyl chloride In tetrahydrofuran; mineral oil for 2h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating / reflux; | 100% |
With potassium carbonate In acetone Heating / reflux; | 100% |
With potassium carbonate In acetone Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With sodium acetate In ethanol at 80℃; for 4h; | 99% |
With sodium acetate at 80℃; for 2h; |
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4-hydroxypropiophenone
Conditions | Yield |
---|---|
With indium iodide In tetrahydrofuran at 40℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel; | 98% |
With potassium carbonate at 150 - 160℃; for 4h; | 81% |
ethylene glycol
4-hydroxypropiophenone
2-ethyl-2-(4-hydroxyphenyl)-1,3-dioxolane
Conditions | Yield |
---|---|
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 2.5h; | 98% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 10 - 20℃; for 2h; Temperature; Concentration; | 97.3% |
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 12h; | 97% |
at 75 - 90℃; for 6h; Substitution; | 89.4% |
With sodium hydroxide |
ethyl bromoacetate
4-hydroxypropiophenone
ethyl 2-(4-propionylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Heating / reflux; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; | 94% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; | 94% |
With potassium carbonate In toluene for 48h; Reflux; |
p-methoxybenzyl chloride
4-hydroxypropiophenone
1-{4-[(4-methoxybenzyl)oxy]phenyl}propan-1-one
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In butanone at 20 - 60℃; for 12h; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere; |
chloroacetic acid ethyl ester
4-hydroxypropiophenone
ethyl 2-(4-propionylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h; | 95% |
4-hydroxypropiophenone
O-(4-bromophenyl)hydroxylamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 20℃; for 2h; | 94% |
4-hydroxypropiophenone
trimethyleneglycol
2-ethyl-2-(4-hydroxyphenyl)-1,3-dioxane
Conditions | Yield |
---|---|
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 6h; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 93% |
methanesulfonyl chloride
4-hydroxypropiophenone
4-propionyl-phenyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 5℃; for 1.5h; | 93% |
2-chloro-N,N-diethylethylamine hydrochloride
4-hydroxypropiophenone
1-(4-(2-(diethylamino)ethoxy)phenyl)propan-1-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Heating; | 92% |
With potassium carbonate In butanone |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 24h; Reflux; | 91.5% |
With potassium carbonate In acetone Heating; | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Heating; | 91% |
With potassium carbonate In acetone at 60℃; for 6h; | 72% |
4-hydroxypropiophenone
2-bromo-(4'-hydroxyphenyl)-propan-1-one
Conditions | Yield |
---|---|
With pyridinium hydrobromide perbromide; acetic acid at 20℃; for 3.08333h; Product distribution / selectivity; | 90% |
With pyridinium hydrobromide perbromide; acetic acid at 20℃; for 3h; | 66% |
With bromine In chloroform; ethyl acetate | 61.3% |
Conditions | Yield |
---|---|
palladium on activated charcoal In ethanol at 34℃; under 37503 Torr; for 0.833333h; | 90% |
With palladium on activated charcoal; ethanol Hydrogenation; | |
With methanol; copper oxide-chromium oxide at 115 - 125℃; under 161812 - 176522 Torr; Hydrogenation; |
4-chloro-2,3-(hexamethylene)quinoline
4-hydroxypropiophenone
1-[4-(6,7,8,9,10,11-Hexahydro-cycloocta[b]quinolin-12-yloxy)-phenyl]-propan-1-one
Conditions | Yield |
---|---|
at 140℃; for 24h; | 90% |
trifluoromethylsulfonic anhydride
4-hydroxypropiophenone
4-propionylphenol trifluoromethanesulfonate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; dmap In dichloromethane for 2h; Ambient temperature; | 90% |
With dmap In dichloromethane at -20 - 20℃; Inert atmosphere; | 90% |
With pyridine In dichloromethane at 0 - 20℃; | 88% |
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 88% |
With 2,6-dimethylpyridine; dmap In dichloromethane at 20℃; for 2h; | 14 g |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 85℃; | 90% |
Molecule structure of Paroxypropione (CAS NO.70-70-2):
IUPAC Name: 1-(4-Hydroxyphenyl)propan-1-one
Molecular Formula: C9H10O2
Molecular Weight: 150.174500 g/mol
Melting Point: 36-38 °C(lit.)
Density: 1.104 g/cm3
Melting Point: 36-38 °C(lit.)
Boiling Point: 152-154 °C at 26 mm Hg(lit.)
Flash Point: >230 °F
Index of Refraction: 1.542
Molar Refractivity: 42.79 cm3
Molar Volume: 135.9 cm3
Surface Tension: 42.6 dyne/cm
Methanol Solubility: 0.1 g/mL, clear
Water Solubility: 0.34 g/l (15 °C)
XLogP3: 2
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Tautomer Count: 7
Exact Mass: 150.06808
MonoIsotopic Mass: 150.06808
Topological Polar Surface Area: 37.3
Heavy Atom Count: 11
Canonical SMILES: CCC(=O)C1=CC=C(C=C1)O
InChI: InChI=1S/C9H10O2/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
InChIKey: RARSHUDCJQSEFJ-UHFFFAOYSA-N
EINECS: 202-815-9
Product Categories: Acetophenone Series; Aromatic Propiophenones (substituted); C9; Carbonyl Compounds; Ketones
Paroxypropione (CAS NO.70-70-2) is used as an intermediates of liquid crystals.
1. | ims-rbt TDLo:1600 mg/kg (female 15-30D post):TER | AOGNAX Archivio di Ostetricia e Ginecologia. 66 (1961),286. | ||
2. | orl-mus LD50:3 mg/kg | 85JDAH Organophosphorus Pesticides: Organic and Biological Chemistry Eto, M.,Cleveland, OH.: CRC Press, Inc.,1974,197. | ||
3. | ipr-mus LD50:200 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . | ||
4. | scu-mus LD50:1130 µg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 124 (1960),212. | ||
5. | par-frg LD50:91 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 124 (1960),212. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xn, Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 37-24/25-36-26
S37:Wear suitable gloves.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: UH1925000
HS Code: 29145000
Hazardous Substances Data: 70-70-2(Hazardous Substances Data)
Poison by intraperitoneal, subcutaneous, and parenteral routes. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
DOT Classification: 3; Label: Flammable Liquid
Paroxypropione (CAS NO.70-70-2) is also named as 1-(4-Hydroxyphenyl)-1-propanone ; 1-(p-Hydroxyphenyl)-1-propanone ; 4-08-00-00441 (Beilstein Handbook Reference) ; 4-Hydroxypropiophenone ; 4-Propionylphenol ; AI3-03719 ; B 360 ; Ethyl p-hydroxyphenyl ketone ; Frenantol ; Frenohypon ; Frenon ; Frenormon ; H 365 ; Paroxipropiona ; Paroxipropiona [INN-Spanish] ; Paroxon ; Possipione ; Profenone ; Proxiphenon ; Sterofenon ; UNII-X9952001TG ; USAF EK-3302 ; p-Hydroxyphenyl-1-propanone ; p-Hydroxypropiophenone ; p-Oxypropiophenone ; p-Propionylphenol ; p-Propiophenol . Paroxypropione (CAS NO.70-70-2) is white powder. It is slightly soluble in water, soluble in boiling water, with alcohol, ether immiscibility.
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