Conditions | Yield |
---|---|
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h; | 100% |
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran at 20℃; Reduction; | 100% |
With sodium tetrahydroborate In methanol at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With methanol; potassium permanganate at 25℃; chemoselective reaction; | 99% |
With 2,2-dibutyl-1,3,2-dioxastannane; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; | 83% |
piperonol
Conditions | Yield |
---|---|
With silica gel In hexane; ethyl acetate | 99% |
With silica gel at 25℃; Inert atmosphere; Glovebox; | 97% |
With silica gel In hexane; ethyl acetate at 20℃; | 143.1 mg |
With air In diethyl ether | 146 mg |
piperonol
Conditions | Yield |
---|---|
With Decaborane In methanol at 20℃; for 0.416667h; | 98% |
With potassium hydrogensulfate In methanol at 20℃; for 2h; | 90% |
In water; dimethyl sulfoxide at 90℃; for 8h; | 84% |
piperonol
Conditions | Yield |
---|---|
With Decaborane In methanol at 20℃; for 0.1h; | 97% |
3,4-(methylenedioxy)benzyl trimethylsilyl ether
piperonol
Conditions | Yield |
---|---|
With Nafion-H(R); silica gel In hexane at 20℃; for 0.5h; | 95% |
With Kaolinitic clay; water for 0.0333333h; Irradiation; microwave; | 63% |
piperonol
Conditions | Yield |
---|---|
With methanol; sodium hydroxide for 6h; Reflux; | 94% |
5-(tetrahydro-2H-pyran-2-yloxy)methylbenzo[d][1,3]dioxole
piperonol
Conditions | Yield |
---|---|
With trichloroisocyanuric acid In methanol at 20℃; for 4h; | 92% |
With cerium(III) chloride In methanol at 20℃; for 0.5h; detetrahydropyranylation; | 90% |
With carbon tetrabromide In methanol at 65℃; for 0.5h; Heating; | 89% |
piperonol
Conditions | Yield |
---|---|
With Nonafluorobutanesulfonyl fluoride; TPGS-750-M In propan-1-ol; water at 50℃; for 12h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 92% |
piperonol
Conditions | Yield |
---|---|
With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; | 89% |
Conditions | Yield |
---|---|
Stage #1: piperonal With diisobutylaluminium hydride In dichloromethane at -78℃; for 1.5h; Stage #2: methanol at 20℃; | 89% |
piperonol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 25℃; for 12h; | 89% |
piperonal
A
piperonol
B
1,2-bis(3,4-dioxymethylenephenyl)ethane-1,2-diol
Conditions | Yield |
---|---|
With vanadium(II) chloride In ethanol; water at 17 - 22℃; for 0.416667h; sonication; | A 1% B 87% |
With sodium hydroxide; aluminium In methanol at 20℃; for 0.5h; Irradiation; | A 6% B 70% |
With magnesium In water at 20℃; for 4h; ultrasonic irradiation; Title compound not separated from byproducts; | A 5% B 60% |
With naphthalene; lithium; manganese(ll) chloride In tetrahydrofuran at 50 - 54℃; for 1h; sonication; | A 9% B 41% |
With water; zinc(II) chloride; zinc In tetrahydrofuran at 25 - 30℃; for 4h; ultrasonication; | A 11.5% B 33.1% |
dimetilamide dell'acido 3,4-metilendiossibenzoico
piperonol
Conditions | Yield |
---|---|
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 7h; Sealed tube; | 87% |
Conditions | Yield |
---|---|
Stage #1: 1,3-benzodioxol-5-yl--methanethione With sodium iodide; Merrifield resin In water; N,N-dimethyl-formamide at 100℃; for 24h; Solid phase reaction; Stage #2: With lithium borohydride In tetrahydrofuran at 20℃; for 5h; Solid phase reaction; | 83% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)oxovanadium; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate at 120℃; for 48h; | A 82% B 82% |
piperonal
6-bromopiperonyl alcohol
A
piperonol
B
benzo[1,3]dioxol-5-yl-(6-(hydroxymethyl)benzo[1,3]dioxol-5-yl)methanol
Conditions | Yield |
---|---|
Stage #1: 6-bromopiperonyl alcohol With n-butyllithium In tetrahydrofuran; hexane for 1h; Stage #2: piperonal In tetrahydrofuran; hexane at -78℃; for 0.666667h; | A 19% B 81% |
piperonol
Conditions | Yield |
---|---|
Stage #1: iodo-acetic acid benzo[1,3]dioxol-5-ylmethyl ester With N-ethyl-N,N-diisopropylamine; aminomethyl polystyrene In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: With benzyl isothiocyanate In N,N-dimethyl-formamide; toluene at 20℃; for 8h; Stage #3: With diisopropylamine at 20℃; for 1h; | 80% |
5-(tetrahydro-2H-pyran-2-yloxy)methylbenzo[d][1,3]dioxole
A
piperonol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; ethanethiol In dichloromethane at -20 - 0℃; for 0.5h; | A 77% B 23% |
5-(tetrahydro-2H-pyran-2-yloxy)methylbenzo[d][1,3]dioxole
ethanethiol
A
piperonol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -20 - 0℃; for 0.5h; | A 77% B 23% |
piperonal
dichloromethane
A
5-vinyl-1,3-benzodioxole
B
piperonol
Conditions | Yield |
---|---|
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; for 0.833333h; | A 75% B 8% |
5-(2-Methoxy-ethoxymethoxymethyl)-benzo[1,3]dioxole
A
piperonol
B
5-(iodomethyl)benzo[d][1,3]dioxole
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In acetonitrile at -20℃; for 2.5h; | A 71% B n/a |
6-bromopiperonyl alcohol
3,4-dimethoxy-benzaldehyde
A
piperonol
B
(3,4-dimethoxyphenyl)-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol
Conditions | Yield |
---|---|
Stage #1: 6-bromopiperonyl alcohol With n-butyllithium In tetrahydrofuran; hexane for 1h; Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran; hexane for 0.666667h; | A 30% B 69% |
Conditions | Yield |
---|---|
With [Ir(κ2O,O-CH3COO)(I)2{κC,C'-methylenebis(N-methyl)imidazole-2-ylidene}]; water; glycerol; potassium hydroxide at 120℃; for 16h; | 67% |
Conditions | Yield |
---|---|
bis(benzene)chromium(0) In benzene at 70℃; for 3h; Reduction; | A 65% B n/a |
2-(benzo[d][1,3]dioxol-6-yl)-2-hydroxyacetonitrile
piperonol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; ethanol at 20℃; for 0.75h; | 65% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 0.25h; chemoselective reaction; | A 28% B 61% |
6-bromopiperonyl alcohol
A
piperonol
B
6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide | A 59% B 15% |
piperonol
5-(chloromethyl)-1,3-benzodioxole
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide at 20℃; for 0.333333h; chemoselective reaction; | 100% |
With thionyl chloride; triethylamine In benzene at 0℃; for 24h; | 100% |
With thionyl chloride In benzene | 98% |
Conditions | Yield |
---|---|
With phosphorus tribromide In benzene at 20℃; | 100% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 2h; | 97% |
With phosphorus tribromide In diethyl ether at 0℃; for 0.75h; Inert atmosphere; | 96% |
piperonol
6-iodo-1,3-benzodioxole-5-methanol
Conditions | Yield |
---|---|
With iodine; silver trifluoroacetate In methanol; dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 100% |
With iodine; silver trifluoroacetate In methanol; dichloromethane at 0 - 20℃; for 14h; Inert atmosphere; | 100% |
With iodine; silver trifluoroacetate In chloroform at 20℃; | 99% |
Conditions | Yield |
---|---|
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.5h; Ambient temperature; | 100% |
With 2,2'-bipyridylchromium peroxide In benzene for 1.25h; Heating; | 100% |
With dipyridinium dichromate; chloro-trimethyl-silane In dichloromethane for 0.25h; | 100% |
piperonol
Phosphorous acid tribenzo[1,3]dioxol-5-ylmethyl ester
Conditions | Yield |
---|---|
With Hexamethylphosphorous triamide at 100℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at 5℃; for 2h; | 100% |
With N-Bromosuccinimide In dichloromethane | |
With N-Bromosuccinimide |
Conditions | Yield |
---|---|
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 20℃; for 24h; | 100% |
Stage #1: piperonol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere; | 99% |
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure; | 99% |
piperonol
2,3-bis(methoxycarbonyl)phenol
3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid dimethyl ester
Conditions | Yield |
---|---|
With PS-triphenylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; not specified; | 100% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
With triethylamine In dichloromethane at 20℃; | 97% |
piperonol
triphenylphosphine
(benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 6.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol; chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll); potassium carbonate at 100℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With polystyrene supported triphenylphosphine ruthenium complex In toluene at 140℃; for 48h; Sealed tube; Flow reactor; | 98% |
With NiCuFeO(x) In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Inert atmosphere; Sealed tube; Reflux; | 93% |
piperonol
toluene-4-sulfonamide
N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With potassium tert-butylate; copper diacetate In toluene at 150℃; for 120h; Inert atmosphere; | 99% |
With potassium hydroxide In toluene at 130℃; for 96h; Inert atmosphere; | 99% |
With palladium diacetate; potassium carbonate In toluene at 150℃; for 8h; | 97% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 150℃; for 24.1667h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With potassium hydroxide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] at 110℃; for 15h; Inert atmosphere; Neat (no solvent); | 99% |
With rhodium(III) chloride hydrate; triphenylphosphine; sodium hydroxide at 110℃; for 20h; Inert atmosphere; | 79% |
With rhodium(III) chloride hydrate; triphenylphosphine; sodium hydroxide at 110 - 115℃; Sealed tube; Inert atmosphere; | 74% |
4-aminopyridine
piperonol
N-(benzo[d][1,3]dioxol-5-ylmethyl)pyridin-4-amine
Conditions | Yield |
---|---|
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h; Inert atmosphere; | 99% |
With cesium hydroxide; palladium diacetate In toluene at 150℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane | 99% |
Conditions | Yield |
---|---|
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 4.5h; Green chemistry; | 99% |
piperonol
sodium S-(4-chlorobenzyl) thiosulfate
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 12h; | 99% |
Conditions | Yield |
---|---|
Stage #1: piperonol With oxygen at 106℃; under 3800.26 Torr; for 0.216667h; Flow reactor; Green chemistry; Stage #2: 2-amino-phenol at 106℃; Flow reactor; Green chemistry; Stage #3: at 106℃; for 0.666667h; Flow reactor; Green chemistry; | 99% |
piperonol
N,N-dimethyl-formamide
benzo[d][1,3]dioxol-5-ylmethyl formate
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; caesium carbonate at 20℃; for 12h; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate at 60℃; under 750.075 Torr; for 2h; Temperature; Pressure; | 98.8% |
With oxygen at 70℃; under 750.075 Torr; for 16h; | 98% |
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h; | 87% |
piperonol
tert-Octylamine
(E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-2,4,4-trimethylpentan-2-amine
Conditions | Yield |
---|---|
With palladium on aluminium oxyhydroxide; oxygen at 90℃; under 760.051 Torr; for 24h; | 98% |
piperonol
1-Phenyl-1H-tetrazole-5-thiol
5-((benzo[d][1,3]dioxol-5-ylmethyl)thio)-1-phenyl-1H-tetrazole
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 0.55h; | 98% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; Mitsunobu type reaction; Inert atmosphere; | 95% |
piperonol
4-methoxybenzene sulfonamide
N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxybenzenesulfonamide
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In toluene at 150℃; for 8h; | 98% |
With potassium tert-butylate; copper diacetate In toluene at 150℃; for 120h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [{Cu(NO3)}(μ-3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide)]2; oxygen; potassium carbonate at 50℃; for 24h; | 98% |
Molecular Structure:
Molecular Formula: C8H8O3
Molecular Weight: 152.1473
IUPAC Name: 1,3-Benzodioxol-5-ylmethanol
Synonyms of Piperonyl alcohol (CAS NO.495-76-1): 1-Hydroxymethyl-3,4-methylenedioxybenzene ; 5-Hydroxymethyl-1,3-benzodioxole ; AI3-05702 ; Benzyl alcohol, 3,4-(methylenedioxy)- ; EINECS 207-808-4 ; Heliotropyl alcohol ; NSC 26265 ; Piperonol ; 1,3-Benzodioxole-5-methanol
CAS NO: 495-76-1
Classification Code: Benzhydrols, Benzyl & Special Alcohols
Melting point: 50-54 °C
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 27.69 Å2
Index of Refraction: 1.594
Molar Refractivity: 38.86 cm3
Molar Volume: 114.4 cm3
Surface Tension: 58.2 dyne/cm
Density: 1.329 g/cm3
Flash Point: 124.5 °C
Enthalpy of Vaporization: 55.04 kJ/mol
Boiling Point: 282.2 °C at 760 mmHg
Vapour Pressure of Piperonyl alcohol (CAS NO.495-76-1): 0.00161 mmHg at 25°C
Hazard Codes of Piperonyl alcohol (CAS NO.495-76-1): Xi
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29329970
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