Benzalacetone supplier | CasNO.122-57-6

Name
Benzalacetone
EINECS 204-555-1
CAS No. 122-57-6
Article Data341
CAS DataBase
Density 1.014 g/cm³
Solubility 1.398g/L(25 oC)
Melting Point 39-42 °C(lit.)
Formula C₁₀H₁₀O
Boiling Point 260.8 °C at 760 mmHg
Molecular Weight 146.189
Flash Point 65.6 °C
Transport Information
Appearance yellow solid
Safety 7-26-36/37/39-45-37/39-24-36/37-22
Risk Codes 36/37/38-43-42/43
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 2-Butenone,4-phenyl- (2CI);Ketone, methyl styryl (7CI);1-Phenyl-1-buten-3-one;2-Phenylethenyl methyl ketone;2-Phenylvinyl methyl ketone;4-Phenyl-3-buten-2-one;4-Phenyl-3-butene-2-one;4-Phenylbutenone;Acetocinnamone;Methyl 2-phenylvinyl ketone;Methyl phenylvinyl ketone;Methyl styryl ketone;Methyl b-styryl ketone;NSC 5605;Styrylmethyl ketone;
PSA 17.07000
LogP 2.28880

Synthetic route

: 17488-65-2
4-phenylbut-3-en-2-ol

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With dicarbonyl-(2,4-bis(trimethylsilyl)bicyclo[3.3.0]nona-1,4-dien-3-one)[acetonitrile]iron; acetone at 90℃; for 18h; Opppenauer oxidation; Inert atmosphere;	99%
With aluminum oxide; potassium permanganate In neat (no solvent) for 0.05h;	97%
With benzyltriphenylphosphonium peroxymonosulfate for 0.0833333h; Oxidation;	97%

: 29833-94-1
2-Methyl-2-((E)-styryl)-[1,3]dithiane

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With dihydrogen peroxide; niobium pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 0.25h;	98%
With iron(III)-acetylacetonate; dihydrogen peroxide; sodium iodide In water; ethyl acetate at 20℃; for 0.2h;	95%
With antimonypentachloride In dichloromethane at 0℃; for 0.166667h;	75%
With oxygen; 2,4,6-tris(p-chlorophenyl)pyrylium perchlorate In dichloromethane for 1.5h; Irradiation;	50%
With methyltriphenylphosphonium tribromide; water 1.) THF, 3 h, room temperature; Yield given. Multistep reaction;

: 108-86-1
bromobenzene

: 78-94-4
methyl vinyl ketone

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 110℃; for 20h; Heck Reaction; Green chemistry;	90%
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl-ammonium chloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Microwave irradiation; Inert atmosphere;

: 100-52-7
benzaldehyde

: 67-64-1
acetone

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With sodium hydroxide In water Aldol Condensation;	96%
With N,N-dimethyl-cyclohexanamine In water at 70℃; for 24h; Aldol Condensation; Green chemistry;	94%
With C66H78O6(6-)*6Na(1+) at 55℃; for 1h; Reagent/catalyst;	93.5%

: 78-94-4
methyl vinyl ketone

: 108-90-7
chlorobenzene

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 110℃; for 20h; Heck Reaction; Green chemistry;	70%

: 123-42-2
4-Hydroxy-4-methyl-2-pentanone

: 100-52-7
benzaldehyde

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With [1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene]copper(I) chloride; sodium t-butanolate In toluene at 20℃; for 3h; Aldol Condensation; Schlenk technique; Inert atmosphere;	90%

: 6249-79-2, 57134-72-2, 84033-96-5, 144667-51-6, 144667-52-7, 146388-50-3
1-(3-phenyloxiran-2-yl)ethanone

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 6000.6 Torr; for 24h; Glovebox; chemoselective reaction;	89%
With carbon monoxide In tetrahydrofuran; water at 110℃; under 6840.46 Torr; for 12h; Autoclave; chemoselective reaction;	86%

: 591-50-4
iodobenzene

: 78-94-4
methyl vinyl ketone

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With sodium carbonate; [1,1'-biphenyl]-4-yl(4-([1,1'-biphenyl]-4-yl)-1H-imidazol-2-yl)methanone; palladium dichloride In water; N,N-dimethyl-formamide at 80℃; for 8h; Heck Reaction; Sealed tube; stereoselective reaction;	94%
With palladium diacetate; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 120℃; under 375.038 - 2250.23 Torr; for 1h; Reagent/catalyst; Temperature; Heck Reaction; Microwave irradiation;	81%
With C33H33N2(1+)*Cl(1-); palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide for 2h; Heck Reaction; Inert atmosphere; Sealed tube; Heating;	79%

: 100-52-7
benzaldehyde

: 67-64-1
acetone

A: 538-58-9
1,5-diphenyl-1,4-pentadiene-3-one

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With diethyl ether; magnesium bromide-butylate
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 60℃; for 0.5h; Inert atmosphere;
With chromium(VI) oxide at 56℃; for 10h;
Aldol Condensation;
With sodium dodecyl-sulfate; sodium hydroxide In water at 40℃; for 4h; Solvent; Claisen-Schmidt Condensation; Sealed tube;

...Expand

: 100-52-7
benzaldehyde

: 67-64-1
acetone

A: 122-57-6
1-Phenylbut-1-en-3-one

B: 5337-88-2
3-methyl-5-phenyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; rac-methylbenzylamine; silver carbonate at 80℃; for 24h; Robinson Annulation; Sealed tube;	A 10% B 65%
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; rac-methylbenzylamine; silver carbonate at 80℃; for 14h; Robinson Annulation; Sealed tube;	A 42% B 40%

...Expand

: 1817-57-8
4-phenyl-3-butyne-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With palladium Hydrogenation;
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulphonic acid / H2O / 0.58 h / 0 °C 2: H3C-COONa, K2Te / 4 h / Ambient temperature View Scheme
With formic acid; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; triethylamine; [Pd(1,4-di-t-butyl-1,4-diazabutadiene)(maleic anhydride)] In para-xylene; acetonitrile for 24h; Heating;
With hydrogen under 760.051 Torr; Reagent/catalyst;

: 2887-98-1
benzalacetone oxime

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 28h; Heating;	95%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.75h; Oxidation; Heating;	90%
With KMnO4/alumina at 50℃; for 0.166667h;	87%
With aluminium trichloride; butyltriphenylphosphonium dichromate In chloroform for 0.75h; Oxidation; Heating;	70%
With gold(III) tribromide; dimethylglyoxal In ethanol; water at 60℃; for 15h; pH=7;	91 %Spectr.

: 598-32-3
2-hydroxy-3-butene

: 98-80-6
phenylboronic acid

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-hydroxy-3-butene With oxygen; palladium diacetate In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 4h; Green chemistry; Stage #2: phenylboronic acid With 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 90℃; for 18h; Heck Reaction; Green chemistry;	85%

: 17488-65-2
4-phenylbut-3-en-2-ol

A: 17488-65-2, 31915-95-4, 36004-04-3, 62413-47-2, 76946-09-3, 81176-43-4, 84519-62-0, 92075-80-4, 104974-60-9, 123536-30-1, 140461-14-9, 32271-52-6
(R)-4-phenyl-3-buten-2-ol

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With Arabidopsis thaliana berberine bridge enzyme-like protein 15 L182V; oxygen In dimethyl sulfoxide at 30℃; for 24h; pH=7.0; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	A 42 %Chromat. B 58 %Chromat.

: 32398-66-6
1-phenylbut-2-yn-1-ol

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With KSF clay for 0.0833333h; Irradiation; microwave irradiation;	92%
With [Ag{μ2-N,S-(1,3,5-triaza-7-phosphaadamantane)=NP(=S)(OEt)2}]x[SbF6]x In water at 160℃; for 1h; Microwave irradiation;	90%

: 22956-11-2
4-Phenyl-4-phenylsulfanyl-butan-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With diiodomethane; diethylzinc; trifluoroacetic acid In dichloromethane at 0℃;	95%

: 100-52-7
benzaldehyde

: 67-64-1
acetone

A: 5381-93-1, 86734-67-0, 86734-69-2, 127707-68-0
(4S)-4-hydroxy-4-phenylbutan-2-one

B: 5381-93-1, 86734-69-2, 127707-68-0, 86734-67-0
(4R)-4-hydroxy-4-phenylbutan-2-one

C: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With 1H-imidazole at 20℃; under 45004.5 Torr; Aldol Addition; Flow reactor; Sonication; stereoselective reaction;	A n/a B n/a C 13%
L-proline In various solvent(s) at 20℃; for 20h; Product distribution; Further Variations:; Solvents; catalyst amounts;
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In dimethyl sulfoxide at 60℃; for 0.5h; Aldol condensation; microreactor; optical yield given as %ee; enantioselective reaction;	A n/a B n/a C 18 %Spectr.
With Zn(2+)C8H5NO4(2-)2C5H9NO2 In dimethyl sulfoxide at 40℃; for 96h; Catalytic behavior; Reagent/catalyst; Temperature; Aldol Addition; Green chemistry; Optical yield = 73 %ee; enantioselective reaction;
Stage #1: acetone With L-proline In chloroform; dimethyl sulfoxide at 0℃; for 0.5h; Aldol Addition; Sealed tube; Stage #2: benzaldehyde In chloroform; dimethyl sulfoxide at 0℃; for 96h; Concentration; Time; Temperature; Solvent; Aldol Addition; Sealed tube; enantioselective reaction;	A n/a B 76 %Spectr. C 8 %Spectr.

...Expand

: 53309-95-8
(+/-)-2-amino-4-phenylbut-3-ene

: 6249-79-2, 57134-72-2, 84033-96-5, 144667-51-6, 144667-52-7, 146388-50-3
trans-2-acetyl-3-phenyloxirane

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With 4-phenylnaphthalene-1,2-dione In acetonitrile at 23℃; for 60h;	A 15% B 15%

: 909413-25-8
6-(tert-butyl)-12-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine

: 78-94-4
methyl vinyl ketone

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With palladium diacetate In 1,4-dioxane; water for 24h; Heating; Inert atmosphere;	79%
With palladium diacetate In 1,4-dioxane; water at 100℃; for 1h; Mizoroki-Heck reaction; Inert atmosphere;	79%

: 4353-00-8
4-phenyl-3-butene-2-one ethylene acetal

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With caro's acid; silica gel In acetonitrile at 20℃; for 0.366667h;	90%

: 1223632-87-8, 960601-06-3
2-(trimethylsilyl)-4-phenyl-3-butyn-2-ol

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran	100%

: C24H18O2

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 5h; Inert atmosphere;	100%

: 6310-44-7
3,4-dibromo-4-phenylbutan-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With ammonium chloride; zinc In ethanol at 80℃; for 0.00833333h; microwave irradiation;	95%
With iron(II) oxalate In N,N-dimethyl-formamide at 100℃; for 2h;	92%
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.5h;	90%

: 74896-58-5
4-ethylsulfanyl-4-phenyl-butan-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) ice-bath, 2.) r.t., 15 h;	89%
With aluminum oxide; potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate 1.) 6 h, room temperature 2.) CH2Cl2, 40 min, room temperature; Yield given. Multistep reaction;

: 4438-85-1
3H-chromene-2,4-dione

: 32398-66-6
1-phenylbut-2-yn-1-ol

A: 15151-14-1
2-methyl-4-phenylpyrano[3,2-c]chromen-5(4H)-one

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With C24H20N2O4Ru; trifluoroacetic acid In toluene at 100℃; for 3h; Inert atmosphere;	A 82% B 8%

...Expand

: 3-((3-oxo-1-phenylbutyl)thio)propyl methanethioate

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With Raney-Ni In methanol at 70℃; for 12h; Reagent/catalyst; Inert atmosphere;	84%

: 130043-06-0
2-[(tert-butyldimethylsilyl)oxy]-4-phenyl-1,3-butadiene

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With (1,10-phenanthroline)(triphenylphosphine)CuBr; sodium 2,2,2-trifluoroacetate In acetonitrile at 80℃; for 3h;	7 %Spectr.
With 7,8-benzoquinoline; trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate In toluene at 80℃; for 1h; Reagent/catalyst;	55 %Spectr.

: (S,E)-4-(tert-butyl)-3-(3-oxobut-1-en-1-yl)oxazolidin-2-one

: 98-80-6
phenylboronic acid

A: (S)-4-(tert-butyl)-3-((R)-3-oxo-1-phenylbutyl)oxazolidin-2-one

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With [2,2]bipyridinyl; water; palladium diacetate at 70℃; for 12h; Temperature; Sealed tube; Schlenk technique; diastereoselective reaction;	A n/a B 6 %Spectr.

...Expand

: C10H11N*ClH

: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With ethanol; potassium hydrogencarbonate; silver nitrate In water at 70℃; for 8h;	72%

: 6310-44-7
3,4-dibromo-4-phenylbutan-2-one

A: 10541-24-9
α-bromobenzalacetone

B: 122-57-6
1-Phenylbut-1-en-3-one

Conditions

Conditions	Yield
With N,N-dimethyl-formamide at 155 - 160℃; for 1h;	A 17% B 74%
With N,N-dimethyl-formamide at 155 - 160℃; for 1h;	A 17% B 73%

: 122-57-6
1-Phenylbut-1-en-3-one

: 6249-79-2, 57134-72-2, 84033-96-5, 144667-51-6, 144667-52-7, 146388-50-3
1-(3-phenyloxiran-2-yl)ethanone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; potassium fluoride on basic alumina In decane; toluene at 25℃; for 24h; Inert atmosphere;	100%
With sodium hydroxide In 1,4-dioxane; water for 20h; Reflux;	95%
With Amberlyst A-26 (OH- form); dihydrogen peroxide In 1,4-dioxane at 20℃; for 6h;	94%

: 122-57-6
1-Phenylbut-1-en-3-one

: 2550-26-7
4-Phenyl-2-butanone

Conditions

Conditions	Yield
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 2h; Ambient temperature;	100%
With hydrogen In toluene at 70℃; under 750.075 Torr; for 0.666667h;	100%
With C50H57IrN2P; hydrogen In dichloromethane at -78 - 20℃;	100%

: 75-52-5
nitromethane

: 122-57-6
1-Phenylbut-1-en-3-one

: 122348-55-4, 122348-59-8, 142232-08-4, 1574-86-3
5-nitro-4-phenylpentan-2-one

Conditions

Conditions	Yield
With hydrotalcite for 0.1h; Michael addition; Microwave irradiation;	100%
With potassium fluoride; 18-crown-6 ether In acetonitrile for 168h; Heating;	93%
With C10H20NaO5*HO(1-); water In methanol at 25℃; for 0.833333h; Michael addition;	90%

: 7393-43-3
tetraallyl tin

: 122-57-6
1-Phenylbut-1-en-3-one

: 21573-75-1
3-methyl-1-phenyl-hexa-1,5-dien-3-ol

Conditions

Conditions	Yield
2,6-dimethylpyridine; zinc trifluoromethanesulfonate In dichloromethane at 20℃; for 24h;	100%
With 4C33H36BO6(3-)4Nd(3+)2C3H7NO14H2OCO3(2-)*2C2H8N(1+); sodium dodecyl-sulfate In water at 20℃; for 48h; chemoselective reaction;	81.4%
With n-butyllithium; cerium(III) chloride 1.) hexane, THF, RT, 1 h, 2.) hexane, THF, 0 deg C, 1 h; Yield given. Multistep reaction;
With 1,1'-bi-2-naphthol

: 1184-53-8
methylcopper

: 122-57-6
1-Phenylbut-1-en-3-one

: 17913-10-9
1-methyl-3-phenyl-butanal

Conditions

Conditions	Yield
With chloro-trimethyl-silane In dichloromethane for 5h;	100%

: 122-57-6
1-Phenylbut-1-en-3-one

: 17488-65-2
4-phenylbut-3-en-2-ol

Conditions

Conditions	Yield
With diphenylsilane; cesium fluoride at 25℃; for 0.5h;	100%
With potassium tert-butylate; hydrogen; potassium isopropoxide; [Ru((R,R)-cyP2N2)HCL] at 20℃; under 22801.5 Torr; for 12h; Conversion of starting material;	100%
With potassium tert-butylate; hydrogen; potassium isopropoxide; Ru((R,R)-cyP2(NH)2)HCl at 20℃; under 22801.5 Torr; for 12h; Conversion of starting material;	100%

: 7677-24-9
trimethylsilyl cyanide

: 122-57-6
1-Phenylbut-1-en-3-one

: 2-phenyl-4-trimethylsilyloxy-3-pentenenitrile

Conditions

Conditions	Yield
With sodium tetrahydroborate at 50℃; for 8.5h; Inert atmosphere;	100%

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 122-57-6
1-Phenylbut-1-en-3-one

: 81-81-2
warfarin

Conditions

Conditions	Yield
With C23H24N2O6S*Li(1+) In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 48h; Reagent/catalyst; Michael Addition;	99%
With lipase In water at 50℃; for 168h; Temperature; Michael Addition; Enzymatic reaction;	99.1%
With N-ethyl-N,N-diisopropylamine In water for 20h; Michael Addition; Reflux;	93%

: 104-47-2
p-methoxybenzylnitrile

: 122-57-6
1-Phenylbut-1-en-3-one

: 102118-66-1, 102118-67-2, 114879-80-0, 114879-87-7
(methoxy-4 phenyl)-1 phenyl-2 oxo-4 pentane carbonitrile

Conditions

Conditions	Yield
With sodium methylate In methanol for 4h; Ambient temperature;	99%
With tetrabutylammomium bromide; potassium carbonate In toluene at 50℃; for 6h;	70%

: 122-57-6
1-Phenylbut-1-en-3-one

: 6310-44-7, 32147-15-2, 55025-54-2
(3S*,4R*)-3,4-dibromo-3-phenylbutan-2-one

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(dimethylamino)ethyl)thiourea In dichloromethane at 22℃; for 2.5h; optical yield given as %de; diastereospecific reaction;	99%
With 1-(2-diethyl-aminoethyl)-3-methylimidazolium hexafluorophosphate; bromine In water at 10 - 20℃; for 0.25h; stereoselective reaction;	91%
With 4-dimethylaminopyridine tribromide In acetic acid for 6h; Ambient temperature;	85%
With oxone; sodium bromide at 20℃; for 0.666667h; Neat (no solvent); Mechanical ball milling;	81%

: 95-20-5
2-methyl-1H-indole

: 122-57-6
1-Phenylbut-1-en-3-one

: 97355-53-8
4-(2-methyl-1H-indol-3-yl)-4-phenyl-2-butanone

Conditions

Conditions	Yield
With sodium ligninsulfonate-immobilized Sc(OTf)3 In ethanol Michael Addition;	99%
bismuth oxide perchlorate In acetonitrile for 0.75h; Michael addition; ultrasonic irradiation;	93%
bismuth(III) nitrate at 20℃; for 0.166667h; Michael addition; grinding;	92%

: 122-57-6
1-Phenylbut-1-en-3-one

: 73183-34-3
bis(pinacol)diborane

: 4-phenyl-4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-butan-2-one

Conditions

Conditions	Yield
With ethyl cinnamate; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃;	99%
Stage #1: 1-Phenylbut-1-en-3-one; bis(pinacol)diborane With potassium carbonate In methanol; toluene at 60℃; for 2h; Michael type reaction; Inert atmosphere; Stage #2: With water; ammonium chloride In methanol; toluene Inert atmosphere;	99%
Stage #1: bis(pinacol)diborane With copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1-Phenylbut-1-en-3-one In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere;	91%

: 5720-07-0
4-methoxyphenylboronic acid

: 122-57-6
1-Phenylbut-1-en-3-one

: (S)-4-(4-methylphenyl)-4-phenylbutan-2-one

Conditions

Conditions	Yield
With potassium hydroxide at 20℃; for 5h; Product distribution / selectivity;	99%
With potassium carbonate at 20℃; for 5h; Product distribution / selectivity;	96%

: 94839-07-3
3,4-(methylenedioxy)-benzeneboronic acid

: 122-57-6
1-Phenylbut-1-en-3-one

: (S)-4-(3,4-methylenedioxy-phenyl)-4-phenyl-2-butanone

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 5h;	99%

: 122-57-6
1-Phenylbut-1-en-3-one

: 105-53-3
diethyl malonate

: (+)-2-(3-oxo-1-phenylbutyl)malonic acid diethyl ester

Conditions

Conditions	Yield
With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; 4-pyrrolidin-1-ylpyridine In toluene at 20℃; for 72h; Michael Addition; enantioselective reaction;	99%
With C27H37N5OS In tetrahydrofuran at 20℃; for 48h; Michael condensation; optical yield given as %ee; enantioselective reaction;	92%
With (R,R)-1,2-diphenylethylenediamine; benzene-1,2-dicarboxylic acid In ethanol at 20℃; for 168h; Michael Addition; enantioselective reaction;	75%

: 13195-64-7
diisopropyl malonate

: 122-57-6
1-Phenylbut-1-en-3-one

: (-)-2-(3-oxo-1-phenylbutyl)malonic acid diisopropyl ester

Conditions

Conditions	Yield
With N-[(2S)-2-amino-3,3-dimethylbutyl]-4-methylbenzenesulfonamide In toluene at 20℃; for 72h; Michael condensation; optical yield given as %ee; regioselective reaction;	99%
With (S)-3-(1H-indol-3-yl)-N1-propylpropane-1,2-diamine; trifluoroacetic acid In chloroform at 20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction;	72%

: 1797-75-7
diallyl malonate

: 122-57-6
1-Phenylbut-1-en-3-one

: diallyl 2-(3-oxo-1-phenylbutyl)malonate

Conditions

Conditions	Yield
With (S)-3-(1H-indol-3-yl)-N1-propylpropane-1,2-diamine; trifluoroacetic acid In chloroform at 20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction;	99%

: 15014-25-2
malonic acid dibenzyl ester

: 122-57-6
1-Phenylbut-1-en-3-one

: 541508-74-1
(R)-dibenzyl 2-(3-oxo-1-phenylbutyl)malonate

Conditions

Conditions	Yield
With (S)-3-(1H-indol-3-yl)-N1-propylpropane-1,2-diamine; trifluoroacetic acid In chloroform at 20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction;	99%
With N-[(2S)-2-amino-3,3-dimethylbutyl]-4-methylbenzenesulfonamide In toluene at 20℃; for 72h; Michael condensation; optical yield given as %ee; enantioselective reaction;	99%

: 122-57-6
1-Phenylbut-1-en-3-one

: 108-59-8
malonic acid dimethyl ester

: 109012-81-9
dimethyl (R)-(-)-4-oxo-2-phenyl-1,1-pentanedicarboxylate

Conditions

Conditions	Yield
With (S)-3-(1H-indol-3-yl)-N1-propylpropane-1,2-diamine; trifluoroacetic acid In chloroform at 20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction;	99%
With N-[(2S)-2-amino-3,3-dimethylbutyl]-4-methylbenzenesulfonamide In toluene at 20℃; for 72h; Michael condensation; optical yield given as %ee; regioselective reaction;	98%
With C59H86N10O9; benzoic acid In tetrahydrofuran at 40℃; Michael Addition; enantioselective reaction;	97%
With C59H86N10O9; benzoic acid In tetrahydrofuran at 40℃; for 96h; Michael Addition; Sealed tube; enantioselective reaction;	95%

: 75-52-5
nitromethane

: 122-57-6
1-Phenylbut-1-en-3-one

: (4S)-5-nitro-4-phenylpentan-2-one

Conditions

Conditions	Yield
With 9-epi-9-amino-9-deoxyquinine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; benzoic acid at 40℃; for 48h; Catalytic behavior; Reagent/catalyst; Temperature; Michael Addition; enantioselective reaction;	99%
Stage #1: nitromethane With C43H64N4O4; scandium tris(trifluoromethanesulfonate) at 30℃; for 0.5h; Asymmetric Michael addition; Inert atmosphere; Neat (no solvent); Stage #2: 1-Phenylbut-1-en-3-one With dmap at 30℃; for 48h; Asymmetric Michael addition; Inert atmosphere; Neat (no solvent); optical yield given as %ee; enantioselective reaction;	97%
With (S)-N1-cyclohexyl-3,3-dimethylbutane-1,2-diamine; benzoic acid In ethyl acetate at 30℃; for 36h; Michael Addition; enantioselective reaction;	89%

: 848924-85-6
2-(5-methoxy-2-oxoindolin-3-ylidene)malononitrile

: 122-57-6
1-Phenylbut-1-en-3-one

: 1332338-80-3
5'-methoxy-2',5-dioxo-3-phenylspiro[cyclohexane-1,3'-indoline]-2,2-dicarbonitrile

Conditions

Conditions	Yield
With C20H25N3O; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In 1,2-dichloro-ethane at 80℃; for 2h; Double Michael addition; optical yield given as %ee; enantioselective reaction;	99%

: 1332338-72-3
C11H4BrN3O

: 122-57-6
1-Phenylbut-1-en-3-one

: 1332338-85-8
6'-bromo-2',5-dioxo-3-phenylspiro[cyclohexane-1,3'-indoline]-2,2-dicarbonitrile

Conditions

Conditions	Yield
With C20H25N3O; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In 1,2-dichloro-ethane at 80℃; for 3h; Double Michael addition; optical yield given as %ee; enantioselective reaction;	99%

: 1332338-74-5
2-(2-oxo-7-(trifluoromethyl)indolin-3-ylidene)malononitrile

: 122-57-6
1-Phenylbut-1-en-3-one

: 1332338-87-0
2',5-dioxo-3-phenyl-7'-(trifluoromethyl)spiro[cyclohexane-1,3'-indoline]-2,2-dicarbonitrile

Conditions

Conditions	Yield
With C20H25N3O; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In 1,2-dichloro-ethane at 80℃; for 1.5h; Double Michael addition; optical yield given as %ee; enantioselective reaction;	99%

Benzalacetone Consensus Reports

Reported in EPA TSCA Inventory.

Benzalacetone Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

Benzalacetone Specification

The Styryl methyl ketone is an organic compound with the formula C₁₀H₁₀O. The IUPAC name of this chemical is (E)-4-phenylbut-3-en-2-one. With the CAS registry number 122-57-6, it is also named as 2-Phenylvinyl methyl ketone. The product's categories are Pharmaceutical Intermediates; Aromatic Ketones (substituted); Aromatics. Besides, it is a yellow solid, which should be stored in a closed place. It is an organic synthesis intermediate which is used as a spice. It is used as a mordant, fixing agent in dyeing industry.

Physical properties about Styryl methyl ketone are: (1)ACD/LogP: 2.17; (2)ACD/LogD (pH 5.5): 2.17; (3)ACD/LogD (pH 7.4): 2.17; (4)ACD/BCF (pH 5.5): 26.38; (5)ACD/BCF (pH 7.4): 26.38; (6)ACD/KOC (pH 5.5): 362.24; (7)ACD/KOC (pH 7.4): 362.24; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 17.07 Å²; (11)Index of Refraction: 1.563; (12)Molar Refractivity: 46.8 cm³; (13)Molar Volume: 144 cm³; (14)Polarizability: 18.55×10^-24cm³; (15)Surface Tension: 36.9 dyne/cm; (16)Density: 1.014 g/cm³; (17)Flash Point: 65.6 °C; (18)Enthalpy of Vaporization: 49.85 kJ/mol; (19)Boiling Point: 260.8 °C at 760 mmHg; (20)Vapour Pressure: 0.012 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-phenyl-but-3-en-2-one-phenylhydrazone. This reaction will need reagent CuSO₄*5H₂O and solvent tetrahydrofuran, methanol, H₂O. The reaction time is 2 hours by heating. The yield is about 100%.

Uses of Styryl methyl ketone: it can be used to produce 4-phenyl-butan-2-one. It will need reagent diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, SiO₂ and solvent CH₂Cl₂ with reaction time of 8 min. The yield is about 96%.

When you are using this chemical, please be cautious about it as the following:
It may cause sensitisation by inhalation and skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection, do not breathe dust and avoid contact with skin. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=O)C=CC1=CC=CC=C1
(2)Isomeric SMILES: CC(=O)/C=C/C1=CC=CC=C1
(3)InChI: InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
(4)InChIKey: BWHOZHOGCMHOBV-BQYQJAHWSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1210mg/kg (1210mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 617, 1969.
mouse	LD50	intravenous	112mg/kg (112mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 617, 1969.
rat	LD50	oral	2031mg/kg (2031mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION SKIN AND APPENDAGES (SKIN): HAIR: OTHER	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0391-1194,

Product Name

Benzalacetone

Synthetic route

Benzalacetone Consensus Reports

Benzalacetone Standards and Recommendations

Benzalacetone Specification

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