Conditions | Yield |
---|---|
With NaY-supported PhI(OAc)2 at 130℃; for 0.0833333h; Solvent; Concentration; Temperature; Time; Microwave irradiation; | A 91% B 9% |
1-piperonyl-1-propanol
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; for 16h; | 89% |
With pyridinium chlorochromate In dichloromethane at 20℃; for 16h; | 89% |
With chromium(VI) oxide; sulfuric acid In water; acetone at 0 - 20℃; for 3h; | 64.06% |
With potassium dichromate | |
With pyridinium chlorochromate In dichloromethane at 20℃; for 6h; |
Methylenedioxybenzene
propionic acid anhydride
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With methanesulfonic acid at 0 - 5℃; for 4h; Concentration; | 89% |
perchloric acid at 0 - 20℃; for 3h; | 34.5 g |
With aluminum (III) chloride; carbonic acid dimethyl ester at 20℃; Friedel-Crafts Acylation; | |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 24h; |
Conditions | Yield |
---|---|
With pivalaldehyde In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With pivalaldehyde; lithium chloride; magnesium bromide In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Inert atmosphere; | 80% |
2-Bromo-1-<3,4-(methylenedioxy)phenyl>-1-propanol
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In benzene at 80℃; for 3h; | 75% |
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In benzene at 100℃; for 5h; | 75% |
dihydrosafrole
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With formic acid; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 110 - 120℃; for 0.266667h; microwave irradiation; | 73% |
ethylmagnesium bromide
piperonylonitrile
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
Stage #1: ethylmagnesium bromide; piperonylonitrile In tetrahydrofuran at 20℃; Cooling with ice; Stage #2: With sulfuric acid; water In tetrahydrofuran Cooling with ice; | 73% |
isosafrole
A
1-(1,3-benzodioxol-5-yl)-2-propanone
B
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With oxygen; copper(l) chloride; palladium dichloride In water; N,N-dimethyl-formamide at 50℃; for 10h; | A 18% B 66% |
With oxygen; copper(l) chloride; palladium dichloride In water; N,N-dimethyl-formamide at 50℃; for 10h; Product distribution; Reagents; | A 60% B 18% |
1'-hydroxysafrole
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; | 65% |
1-(benzo[d][1,3]dioxol-6-yl)ethanone
N,N-dimethyl-formamide
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube; | 63% |
Methylenedioxybenzene
propionyl chloride
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 20℃; for 1h; | 58% |
With zinc(II) oxide; zinc(II) chloride In dichloromethane at 0 - 5℃; for 5h; Reagent/catalyst; Solvent; | 311 g |
With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation; |
isosafrole
A
piperonal
B
Piperonylic acid
C
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With PhI(OAc)2/Al2O3 at 140℃; for 0.5h; Microwave irradiation; | A 57% B 31% C 12% |
isosafrole
A
piperonal
B
3,4-methylenedioxypropiophenone
C
5-(3-methyl-oxiranyl)-benzo[1,3]dioxole
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene In dichloromethane at 50℃; for 0.0833333h; Time; Temperature; Solvent; Microwave irradiation; | A 29% B 15% C 55% |
dihydrosafrole
acetic acid
A
3,4-methylenedioxypropiophenone
B
1-(3,4-dioxymethylenephenyl)propyl acetate
C
isosafrole
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone | A 17% B 39% C 10% |
dihydrosafrole
acetic acid
A
3,4-methylenedioxypropiophenone
B
1-(3,4-dioxymethylenephenyl)propyl acetate
Conditions | Yield |
---|---|
With potassium permanganate sonication; | A 32% B 16% |
Diazoethan
piperonal
diethyl ether
ethanol
3,4-methylenedioxypropiophenone
piperonal
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With Diazoethan; diethyl ether; ethanol | |
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -78 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 6 h / 20 °C View Scheme |
5-(1,2-dibromo-propyl)-benzo[1,3]dioxole
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With sodium methylate Erwaermen des Reaktionsprodukts mit Salzsaeure; | |
With sodium methylate Erwaermen des Reaktionsprodukts mit Salzsaeure; |
3',4'-dihydroxypropiophenone
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With potassium hydroxide; dichloromethane at 120℃; |
piperonylonitrile
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With diethyl ether; ethylmagnesium bromide Erwaermen des erhaltenen 1-Benzo<1,3>dioxol-5-yl-propan-1-on-imins mit wss. Salzsaeure; |
isosafrole
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With phosphorus pentachloride Zerlegung des Produkts mit Wasser und Kochen des mit Wasserdampf ueberdestillierten Oels mit alkoholischer Kalilauge; |
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With sulfuric acid |
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With chromium(III) oxide; sulfuric acid |
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With hydrogenchloride |
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With hydrogenchloride |
5-(prop-1-yn-1-yl)benzo[d][1,3]dioxole
sulfuric acid
3,4-methylenedioxypropiophenone
phosphorus pentachloride
isosafrole
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
Zerlegung des Reaktionsprodukts mit Wasser und Kochen des mit Wasserdampf destillierten Oels mit alkoh. Kalilauge; |
hydrogenchloride
1ξ-ethoxy-1ξ-benzo[1,3]dioxol-5-yl-propene
3,4-methylenedioxypropiophenone
1-piperonyl-1-propanol
3,4-methylenedioxypropiophenone
3,4-methylenedioxypropiophenone
1-piperonyl-1-propanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In isopropyl alcohol at 20℃; for 18h; | 97.1% |
With lithium aluminium tetrahydride In diethyl ether for 0.5h; Heating; | 90% |
With lithium aluminium tetrahydride In diethyl ether for 24h; Heating; | 90 mg |
3,4-methylenedioxypropiophenone
(S)-(-)-α-ethyl-3,4-methylenedioxybenzyl alcohol
Conditions | Yield |
---|---|
With dimethylsulfide; dimethylsulfide borane complex; (R)-2-methyl-(CBS)-oxazaborolidine In dichloromethane; toluene at 20℃; for 4h; | 97% |
With dimethylsulfide; dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane; toluene at 20℃; for 4h; Corey-Bakshi-Shibata reduction; | 97% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 15 - 20℃; for 2.5h; Vilsmeier Formylation; Stage #2: 3,4-methylenedioxypropiophenone In DMF (N,N-dimethyl-formamide) at 35℃; for 6h; Vilsmeier Formylation; Stage #3: With sodium hydroxide; water In DMF (N,N-dimethyl-formamide); toluene at 20 - 25℃; for 7h; Product distribution / selectivity; | 97% |
methanol
3,4-methylenedioxypropiophenone
(±)-1-(benzo[d][1,3]dioxol-5-yl)-2-methylpropan-1-one
Conditions | Yield |
---|---|
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere; | 91% |
3,4-methylenedioxypropiophenone
1-(3,4-(methylenedioxy)phenyl)-2-bromopropan-1-one
Conditions | Yield |
---|---|
With bromine In chloroform at 0℃; | 87% |
With bromine In diethyl ether for 0.5h; Inert atmosphere; | 82% |
With dichloromethane; bromine |
3,4-methylenedioxypropiophenone
1-(4-(benzyloxy)-3-methoxyphenyl)-2-bromopropan-1-one
Conditions | Yield |
---|---|
Stage #1: 3,4-methylenedioxypropiophenone With potassium hexamethylsilazane In N,N-dimethyl-formamide; toluene at -45℃; for 1h; Stage #2: 1-(4-(benzyloxy)-3-methoxyphenyl)-2-bromopropan-1-one In N,N-dimethyl-formamide; toluene at -45℃; | 86% |
3,4-methylenedioxypropiophenone
5-propionyloxy-benzo[1,3]dioxole
Conditions | Yield |
---|---|
With formic acid; dihydrogen peroxide In dichloromethane; water for 6h; | 85% |
With formic acid; dihydrogen peroxide In dichloromethane; water at 47℃; for 12h; Heating / reflux; | 94.5 %Chromat. |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; chloro(1,5-cyclooctadiene)rhodium(I) dimer; copper diacetate; cesium fluoride In toluene at 120℃; for 24h; Inert atmosphere; | 85% |
3,4-methylenedioxypropiophenone
anthranil
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 110℃; for 12h; Molecular sieve; Inert atmosphere; | 83% |
methanol
3,4-methylenedioxypropiophenone
5-(1-methoxypropyl)-1,3-benzodioxolane
Conditions | Yield |
---|---|
With sodium tetrahydroborate at 20℃; for 0.5h; | 81% |
3,4-methylenedioxypropiophenone
3-amino-1-phenylbut-2-en-1-one
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In N,N-dimethyl-formamide at 120℃; for 20h; Sealed tube; regioselective reaction; | 79% |
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In N,N-dimethyl-formamide at 120℃; for 20h; Sealed tube; | 79% |
3,4-methylenedioxypropiophenone
aniline
N-phenylbenzo[d][1,3]dioxole-5-carboxamide
Conditions | Yield |
---|---|
With copper(II) choride dihydrate; oxygen; triphenylphosphine In dimethyl sulfoxide at 120℃; for 20h; Schlenk technique; | 79% |
3,4-methylenedioxypropiophenone
Methanesulfonyl azide
Conditions | Yield |
---|---|
Stage #1: 3,4-methylenedioxypropiophenone With sodium hydride; formic acid ethyl ester In diethyl ether; ethanol; mineral oil at 0 - 20℃; for 15h; Inert atmosphere; Stage #2: Methanesulfonyl azide In diethyl ether; ethanol; mineral oil for 2h; Inert atmosphere; | 74% |
3,4-methylenedioxypropiophenone
benzamidine monohydrochloride
Conditions | Yield |
---|---|
With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube; | 73% |
With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethyl-formamide at 120℃; for 24h; regioselective reaction; | 73% |
3,4-methylenedioxypropiophenone
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide at 80℃; for 6h; Chlorination; | 66% |
3,4-methylenedioxypropiophenone
2,4-dichlorophenyl hydrazine hydrochloride
oxalic acid diethyl ester
1-(2,4-dichlorophenyl)-4-methyl-5-(3,4-methylenedioxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 3,4-methylenedioxypropiophenone; oxalic acid diethyl ester With lithium hexamethyldisilazane In diethyl ether at -78 - 0℃; Stage #2: 2,4-dichlorophenyl hydrazine hydrochloride In ethanol at 20℃; Stage #3: With acetic acid Heating; Further stages.; | 57% |
The 1-Propanone,1-(1,3-benzodioxol-5-yl)- is an organic compound with the formula C10H10O3. The IUPAC name of this chemical is 1-(1,3-benzodioxol-5-yl)propan-1-one. With the CAS registry number 28281-49-4, it is also named as 3',4'-Methylenedioxypropiophenone. The product's categories are Adehydes, Acetals & Ketones. Besides, it should be stored in a closed cool and dry place.
Physical properties about 1-Propanone,1-(1,3-benzodioxol-5-yl)- are: (1)ACD/LogP: 2.31; (2)ACD/LogD (pH 5.5): 2.31; (3)ACD/LogD (pH 7.4): 2.31; (4)ACD/BCF (pH 5.5): 33.43; (5)ACD/BCF (pH 7.4): 33.43; (6)ACD/KOC (pH 5.5): 429.1; (7)ACD/KOC (pH 7.4): 429.1; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 35.53 Å2; (11)Index of Refraction: 1.546; (12)Molar Refractivity: 47.07 cm3; (13)Molar Volume: 148.6 cm3; (14)Polarizability: 18.66×10-24cm3; (15)Surface Tension: 46.2 dyne/cm; (16)Density: 1.198 g/cm3; (17)Flash Point: 130.1 °C; (18)Enthalpy of Vaporization: 54.7 kJ/mol; (19)Boiling Point: 306.4 °C at 760 mmHg; (20)Vapour Pressure: 0.000771 mmHg at 25°C.
Preparation: this chemical can be prepared by benzo[1,3]dioxole and propaionyl chloride. This reaction will need reagent SnCl4 and solvent CH2Cl2. The reaction time is 60 min with reaction temperature of 20 °C. The yield is about 58%.
Uses of 1-Propanone,1-(1,3-benzodioxol-5-yl)-: it can be used to produce 5-(1-methoxy-propyl)-benzo[1,3]dioxole at temperature of 20 °C. It will need reagent NaBH4 with reaction time of 30 min. The yield is about 81%.
When you are using this chemical, please be cautious about it as the following:
This chemical is danger of cumulative effects. When you are using it, wear suitable gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1ccc2OCOc2c1)CC
(2)InChI: InChI=1/C10H10O3/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h3-5H,2,6H2,1H3
(3)InChIKey: RVBJGSPBFIUTTR-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C10H10O3/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h3-5H,2,6H2,1H3
(5)Std. InChIKey: RVBJGSPBFIUTTR-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 2150mg/kg (2150mg/kg) | Pharmaceutical Chemistry Journal Vol. 21, Pg. 341, 1987. |
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