495-76-1

Basic information

• Product Name: Piperonyl alcohol
• Synonyms: 3,4-(Methylenedioxy)benzyl alcohol, (1,3-Benzodioxol-5-yl)methanol;5-(Hydroxymethyl)-1,3-benzodioxole 98%;1-Hydroxymethyl-3,4-methylenedioxybenzene;3,4-(Methylenedioxy)benzenemethanol;5-Hydroxymethyl-1,3-benzodioxole;Benzyl alcohol, 3,4-(methylenedioxy)-;Piperonol;TIMTEC-BB SBB004053
• CAS NO: 495-76-1
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 207-808-4
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;C7 to C8;Oxygen Compounds;Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 495-76-1.mol
• Article Data: 144

Chemical Properties

• Melting Point: 50-54 °C(lit.)
• Boiling Point: 112 °C
• Flash Point: >230 °F
• Appearance: White/Crystals or Crystalline Powder
• Density: 1.2143 (rough estimate)
• Vapor Pressure: 0.00161mmHg at 25°C
• Refractive Index: 1.4945 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.36±0.10(Predicted)
• Water Solubility: soluble
• BRN: 136113
• CAS DataBase Reference: Piperonyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Piperonyl alcohol(495-76-1)
• EPA Substance Registry System: Piperonyl alcohol(495-76-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 495-76-1(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALS OR CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 495-76-1 differently. You can refer to the following data:
1. Piperonyl Alcohol acts as an anti-oxidant on lipid peroxidation through inhibition. It is also used as a reagent in improving stability and antioxidant characteristics of sesame oil through spray-drie d emulsions.
2. Piperonyl Alcohol acts as an anti-oxidant on lipid peroxidation through inhibition. It is also used as a reagent in improving stability and antioxidant characteristics of sesame oil through spray-dried emulsions.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3657, 1949 DOI: 10.1021/ja01179a022

InChI:InChI=1/C8H8O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-3,9H,4-5H2

Synthetic route

piperonal (120-57-0) → piperonol (495-76-1)

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%

piperonyl acetate (326-61-4) → piperonol (495-76-1)

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%

C14H19BO5 → piperonol (495-76-1)

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

(benzo[d][1,3]dioxol-5-ylmethoxy)(tert-butyl)dimethylsilane → piperonol (495-76-1)

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%

(benzo[1,3]dioxol-5-ylmethoxy)-triphenyl-silane → piperonol (495-76-1)

Conditions	Yield
With Decaborane In methanol at 20℃; for 0.1h;	97%

3,4-(methylenedioxy)benzyl trimethylsilyl ether (61040-76-4) → piperonol (495-76-1)

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%

benzo[d][1,3]dioxol-5-ylmethyl quinolin-8-ylcarbamate → piperonol (495-76-1)

Conditions	Yield
With methanol; sodium hydroxide for 6h; Reflux;	94%

5-(tetrahydro-2H-pyran-2-yloxy)methylbenzo[d][1,3]dioxole (85604-71-3) → piperonol (495-76-1)

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%

C21H20O3Si → piperonol (495-76-1)

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; TPGS-750-M In propan-1-ol; water at 50℃; for 12h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	92%

5-[(2-phenylallyloxy)methyl]benzo[d][1,3]dioxole → piperonol (495-76-1)

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;	89%

methanol (67-56-1) + piperonal (120-57-0) → piperonol (495-76-1)

Conditions	Yield
Stage #1: piperonal With diisobutylaluminium hydride In dichloromethane at -78℃; for 1.5h; Stage #2: methanol at 20℃;	89%

benzo[d][1,3]dioxol-5-yl(1H-pyrazol-1-yl)methanone → piperonol (495-76-1)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 25℃; for 12h;	89%

piperonal (120-57-0) → piperonol (495-76-1) + 1,2-bis(3,4-dioxymethylenephenyl)ethane-1,2-diol (4543-59-3)

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 (15777-88-5) → piperonol (495-76-1)

Conditions	Yield
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 7h; Sealed tube;	87%

1,3-benzodioxol-5-yl--methanethione (7501-62-4) → piperonol (495-76-1)

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%

5-[(phenylmethoxy)methyl]-1,3-benzodioxole → piperonol (495-76-1) + benzoic acid (65-85-0)

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 (120-57-0) + 6-bromopiperonyl alcohol (6642-34-8) → piperonol (495-76-1) + benzo[1,3]dioxol-5-yl-(6-(hydroxymethyl)benzo[1,3]dioxol-5-yl)methanol (473253-66-6)

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%

iodo-acetic acid benzo[1,3]dioxol-5-ylmethyl ester → piperonol (495-76-1)

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 (85604-71-3) → piperonol (495-76-1) + 5-Ethylsulfanylmethyl-benzo[1,3]dioxole

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 (85604-71-3) + ethanethiol (75-08-1) → piperonol (495-76-1) + 5-Ethylsulfanylmethyl-benzo[1,3]dioxole

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -20 - 0℃; for 0.5h;	A 77% B 23%

piperonal (120-57-0) + dichloromethane (75-09-2) → 5-vinyl-1,3-benzodioxole (7315-32-4) + piperonol (495-76-1)

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 (91475-97-7) → piperonol (495-76-1) + 5-(iodomethyl)benzo[d][1,3]dioxole (157766-09-1)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile at -20℃; for 2.5h;	A 71% B n/a

6-bromopiperonyl alcohol (6642-34-8) + 3,4-dimethoxy-benzaldehyde (120-14-9) → piperonol (495-76-1) + (3,4-dimethoxyphenyl)-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol (473253-67-7)

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%

1,3-benzodioxol-5-ylmethyl amine (2620-50-0) → piperonol (495-76-1)

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%

piperonal (120-57-0) + diphenylsilane (775-12-2) → piperonol (495-76-1) + bis-(benzo[1,3]dioxol-5-ylmethoxy)-diphenyl-silane

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 (86215-81-8) → piperonol (495-76-1)

Conditions	Yield
With sodium tetrahydroborate; ethanol at 20℃; for 0.75h;	65%

5-[1,3]dioxolan-2-yl-benzo[1,3]dioxole (4405-18-9) → piperonal (120-57-0) + piperonol (495-76-1)

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 0.25h; chemoselective reaction;	A 28% B 61%

6-bromopiperonyl alcohol (6642-34-8) → piperonol (495-76-1) + 6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole (79422-40-5)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide	A 59% B 15%

piperonol (495-76-1) → 5-(chloromethyl)-1,3-benzodioxole (20850-43-5)

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%

piperonol (495-76-1) → 3,4-Methylenedioxybenzyl bromide (2606-51-1)

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 (495-76-1) → 6-iodo-1,3-benzodioxole-5-methanol (69048-76-6)

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%

piperonol (495-76-1) → piperonal (120-57-0)

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 (495-76-1) → Phosphorous acid tribenzo[1,3]dioxol-5-ylmethyl ester (210358-11-5)

Conditions	Yield
With Hexamethylphosphorous triamide at 100℃; for 2h;	100%

piperonol (495-76-1) → 6-bromopiperonyl alcohol (6642-34-8)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 5℃; for 2h;	100%
With N-Bromosuccinimide In dichloromethane
With N-Bromosuccinimide

piperonol (495-76-1) → piperonylonitrile (4421-09-4)

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 (495-76-1) + 2,3-bis(methoxycarbonyl)phenol (36669-02-0) → 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid dimethyl ester (1061606-11-8)

Conditions	Yield
With PS-triphenylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; not specified;	100%

piperonol (495-76-1) + acetyl chloride (75-36-5) → piperonyl acetate (326-61-4)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at 20℃;	97%

piperonol (495-76-1) + triphenylphosphine (603-35-0) → (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide (58005-36-0)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 6.5h; Inert atmosphere;	100%

piperonol (495-76-1) + N-(2-pyridinyl)piperazine (20980-22-7) → piribedil (3605-01-4)

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 (495-76-1) + toluene-4-sulfonamide (70-55-3) → N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methyl-benzenesulfonamide (22102-40-5)

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%

2-oxoindole (59-48-3) + piperonol (495-76-1) → 3-benzo[1,3]dioxol-5-ylmethyl-1,3-dihydroindol-2-one

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 (504-24-5) + piperonol (495-76-1) → N-(benzo[d][1,3]dioxol-5-ylmethyl)pyridin-4-amine (1301628-37-4)

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%

piperonol (495-76-1) + dimethyl sulfate (77-78-1) → benzo[d][1,3]dioxol-5-ylmethyl methyl ether (86633-25-2)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane	99%

vinyl acetate (108-05-4) + piperonol (495-76-1) → piperonyl acetate (326-61-4)

Conditions	Yield
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 4.5h; Green chemistry;	99%

piperonol (495-76-1) + sodium S-(4-chlorobenzyl) thiosulfate (14752-65-9) → 5-(((4-chlorobenzyl)thio)methyl)benzo[d][1,3]dioxole

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	99%

piperonol (495-76-1) + 2-amino-phenol (95-55-6) → 2‐(benzo[d][1,3]dioxol‐5‐yl)benzo[d]oxazole (3315-20-6)

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 (495-76-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → benzo[d][1,3]dioxol-5-ylmethyl formate (85262-96-0)

Conditions	Yield
With fluorosulfonyl fluoride; caesium carbonate at 20℃; for 12h; Sealed tube;	99%

piperonol (495-76-1) + 9H-fluorene (86-73-7) → 5-fluoren-9-ylmethyl-benzo[1,3]dioxole

Conditions	Yield
With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere;	99%

methanol (67-56-1) + piperonol (495-76-1) → methyl 3,4-methylenedioxybenzoate (326-56-7)

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 (495-76-1) + tert-Octylamine (107-45-9) → (E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-2,4,4-trimethylpentan-2-amine (1137195-75-5)

Conditions	Yield
With palladium on aluminium oxyhydroxide; oxygen at 90℃; under 760.051 Torr; for 24h;	98%

piperonol (495-76-1) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-((benzo[d][1,3]dioxol-5-ylmethyl)thio)-1-phenyl-1H-tetrazole (425652-61-5)

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 (495-76-1) + 4-methoxybenzene sulfonamide (1129-26-6) → N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxybenzenesulfonamide (349622-44-2)

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%

piperonol (495-76-1) + ammonia (7664-41-7) → piperonylonitrile (4421-09-4)

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%

Upstream product

• 120-57-0 piperonal 
• 64-17-5 ethanol 
• 91247-76-6 2-(methyl-piperonyl-amino)-ethanol 
• 108-24-7 acetic anhydride 
• 124-41-4 sodium methylate 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 141-05-9 Diethyl maleate 
• 623-91-6 diethyl Fumarate 
• 4111-54-0 lithium diisopropyl amide 
• 85604-71-3 5-(tetrahydro-2H-pyran-2-yloxy)methylbenzo[d][1,3]dioxole 
• 7732-18-5 water 
• 61040-76-4 3,4-(methylenedioxy)benzyl trimethylsilyl ether 
• 6642-34-8 6-bromopiperonyl alcohol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 5442-27-3 5-(1-butoxy-ethoxymethyl)-benzo[1,3]dioxole 
• 5469-06-7 benzo[d][1,3]dioxol-5-ylmethyl benzoate 
• 5432-93-9 4-methoxy-benzoic acid piperonyl ester 
• 5461-08-5 3,4-methylenedioxybenzyl isobutanoate 
• 5457-71-6 chloro-acetic acid piperonyl ester 
• 5457-68-1 5-octanoyloximethyl-benzo[1,3]dioxole 
• 2859-77-0 1-(2-chloro-ethoxy)-1-piperonyloxy-ethane 
• 6976-55-2 5-[1]naphthoyloximethyl-benzo[1,3]dioxole 
• 7145-99-5 5-methyl-1,3-benzodioxole 
• 20850-43-5 5-(chloromethyl)-1,3-benzodioxole 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 15341-08-9 (6-nitrobenzo[d][1,3]dioxol-5-yl)methanol 
• 5434-47-9 5-bromo-6-bromomethylbenzo[1,3]dioxole 
• 85262-96-0 benzo[d][1,3]dioxol-5-ylmethyl formate 

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A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.