24650-42-8

Basic information

• Product Name: 2,2-Dimethoxy-2-phenylacetophenone
• Synonyms: PHOTOCURE 51;2,2-DIMETHOXY-2-PHENYLACETOPHENONE;ALPHA,ALPHA-DIMETHOXY-ALPHA-PHENYLACETOPHENONE;DIMETHYL BENZIL KETAL;BDK;BENZIL DIMETHYL KETAL;BENZIL ALPHA,ALPHA-DIMETHYL ACETAL;1,2-Diphenylethane-1,2-dione,dimethylketal
• CAS NO: 24650-42-8
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• EINECS: 246-386-6
• Product Categories: Photo Initiators;Industrial/Fine Chemicals;Additives for Plastic;Functional Materials;Photopolymerization Initiators;Aromatics
• Mol File: 24650-42-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 67-70 °C(lit.)
• Boiling Point: 169°C 7mm
• Flash Point: 190 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.1320 (rough estimate)
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.5590 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: methylene chloride: 20 mg/mL, clear
• Water Solubility: 66.32mg/L at 25℃
• Stability: Stability Stable, but light-sensitive. Combustible. Incompatible with strong acids, strong oxidizing agents.
• BRN: 2054295
• CAS DataBase Reference: 2,2-Dimethoxy-2-phenylacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethoxy-2-phenylacetophenone(24650-42-8)
• EPA Substance Registry System: 2,2-Dimethoxy-2-phenylacetophenone(24650-42-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: KM5775658
• F: 8
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 24650-42-8(Hazardous Substances Data)

Usage

use

2,2-Dimethoxy-2-phenylacetophenone is a photoinitiator, which is used to initialise radical polymerization e.g. in the preparation of acrylate polymers.[1] Under the influence of light the molecule will form radicals which initiate the radical polymerization. It can also be used as an initiator in the process of making an integrated circuit.

Chemical properties

White crystal, melting point 64.0-67.0 ℃, soluble in acetone, ethyl acetate, hot methanol and isopropanol, insoluble in water, easily decomposed in case of acid, stable in alkaline, photosensitive, mainly used as UV (ultra-violet ) curing agent in UV curing system, applied to ink, paper and metal paint, stored in a sealed package, protected from light and heat.

Enterprise standard reference

loss on drying% ≤0.5 Ignited residue% ≤0.1 Water content? ≤0.5 transparency (10% acetone solution) transparent Benzoin residue? 0.2% Solubility (g/100g solvent 25 ℃) acetone >50 methanol 41 styrene >50 butyl acetate >50 transmission 95.0%(425nm) 96.0%(450nm) 98.0%(500nm)

Application

It is widely used in the polymerization of acrylic acid and acrylate, the polymerization and crosslinking of unsaturated polyester. It has been applied in coatings and adhesives and mainly used as UV (ultra-violet ) curing agent in UV curing system, applied to ink, paper and metal paint. BDK is a kind of highly efficient UV curing initiator, which is mainly used as initiator of UV curing reaction. It is also used as (1) Used as analytical reagent; (2) Used for Photosensitive resin printing; (3)Used as UV curable coatings and inks.

Chemical Properties

solid

Uses

2,2-Dimethoxy-2-phenylacetophenone (cas# 24650-42-8) is a compound useful in organic synthesis.

InChI:InChI=1/C16H16O3/c1-18-16(19-2,14-11-7-4-8-12-14)15(17)13-9-5-3-6-10-13/h3-12H,1-2H3

Synthetic route

sodium methylate (124-41-4) + benzil (134-81-6) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
Stage #1: sodium methylate; benzil With dimethyl sulfate In 1,4-dioxane at 10 - 25℃; Stage #2: With sodium hydroxide In 1,4-dioxane at 105℃;	92.6%

benzil (134-81-6) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With potassium carbonate; phosphorous acid trimethyl ester In methanol; thionyl chloride; water; isopropyl alcohol	84%
With sodium hydroxide; sodium methylate; dimethyl sulfate In 1,4-dioxane; water

methanol (67-56-1) + diphenyl acetylene (501-65-5) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 25℃; for 3h; UV-irradiation; Green chemistry;	82%
With 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 3h; Irradiation;	82%
With thallium(III) nitrate

2-hydroxy-2-phenylacetophenone (119-53-9) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With potassium carbonate; phosphorous acid trimethyl ester In methanol; thionyl chloride; sulfuryl dichloride; water; isopropyl alcohol	79%

methanol (67-56-1) + benzil monohydrazone (5344-88-7) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With sodium acetate; potassium bromide at 15℃; Electrochemical reaction;	77%

methanol (67-56-1) + diphenyl acetylene (501-65-5) → benzoic acid methyl ester (93-58-3) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + 1,2-diphenyl-1,1,2,2-tetramethoxyethane (39787-30-9) + benzil (134-81-6)

Conditions	Yield
With periodic acid for 24h; Heating;	A 5% B 71% C 1% D 5%
With periodic acid Product distribution; Heating;

methanol (67-56-1) + diphenyl acetylene (501-65-5) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + benzil (134-81-6)

Conditions	Yield
With ammonium persulfate; diphenyl diselenide for 1.5h; Heating; Yields of byproduct given;	A 84 % Turnov. B n/a

methanol (67-56-1) + diphenyl acetylene (501-65-5) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + 1,2-diphenyl-1,1,2,2-tetramethoxyethane (39787-30-9) + benzil (134-81-6)

Conditions	Yield
With iodine pentoxide for 24h; Product distribution; Heating; different molar ratios;
With iodine pentoxide for 24h; Heating; Yield given. Yields of byproduct given;

trans-2,3-Dimethoxy-2,3-diphenyl-oxirane → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
at 20℃;

benzil (134-81-6) + methyl iodide (74-88-4) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With barium(II) oxide In N,N-dimethyl-formamide

trans-α,α-dimethoxystilbene (22611-72-9) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.20 mol / ozone / CD2Cl2 / -20 °C 2: 20 °C View Scheme
Multi-step reaction with 2 steps 1: 0.28 mol / ozone / CD2Cl2 / -70 °C 2: 20 °C View Scheme
Multi-step reaction with 2 steps 1: 0.28 mol / ozone / CD2Cl2 / -70 °C 2: 20 °C View Scheme

benzil (134-81-6) + methyl p-toluene sulfonate (80-48-8) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
With sodium methylate In N-methyl-acetamide; water

dimethylsulfite (616-42-2) + sulfuric acid (7664-93-9) + benzil (134-81-6) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8)

Conditions	Yield
In methanol; ligroin

benzoin monomethyl ether (3524-62-7) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + benzil (134-81-6)

Conditions	Yield
With AlCl3(η1-2,2,6,6-tetramethylpiperidine-N-oxyl) In dichloromethane at 25℃; for 15h; Inert atmosphere;	A 16 %Spectr. B 53 %Spectr.

1,2-diphenyl-2-methoxyethanol (58176-63-9) → 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + benzil (134-81-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 2.5 h / Inert atmosphere 2: AlCl3(η1-2,2,6,6-tetramethylpiperidine-N-oxyl) / dichloromethane / 15 h / 25 °C / Inert atmosphere View Scheme

trimethylsilyl cyanide (7677-24-9) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → (+)-1,2-diphenyl-1,1-dimethoxy-2-trimethylsilyloxypropanenitrile

Conditions	Yield
With tert-butyl methyl ether; Ru[t-leu]2[(S)-binap]; lithium phenolate at -20℃; for 30h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	96%

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → benzil (134-81-6)

Conditions	Yield
With Bi(1+)*NO3(1-)=BiNO3 In dichloromethane for 12h; Heating;	95%
bismuth(III) iodide In water at 100℃; for 28.4167h;	93%
With copper(II) sulfate; sodium iodide In acetone at 56℃; for 22h;	84%
With water; toluene-4-sulfonic acid In tetrahydrofuran for 20h; Heating;
With bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water for 12h; Heating;

tetrahydrofuran (109-99-9) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → 2,2-dimethoxy-2-phenyl-1-(4-(tetrahydrofuran-2-yl)phenyl)ethan-1-one

Conditions	Yield
With dipotassium peroxodisulfate; tetrabutyl-ammonium chloride; sodium acetate at 120℃; regioselective reaction;	90%

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → 2-methoxy-1,2-diphenylpent-4-en-1-one (27984-20-9)

Conditions	Yield
With gallium; 18-crown-6 ether; silver trifluoromethanesulfonate In 1,4-dioxane at 40 - 45℃; for 60h; Sonication; Inert atmosphere; chemoselective reaction;	82%

1,4-dioxane (123-91-1) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → 1-(4-(1,4-dioxan-2-yl)phenyl)-2-phenylethane-1,2-dione

Conditions	Yield
With dipotassium peroxodisulfate; tetrabutyl-ammonium chloride; sodium acetate at 120℃; regioselective reaction;	61%

pyrrolidine (123-75-1) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + 1-phenyl-3,4-dimethylphosphole (30540-36-4) → C44H49NO2P2

Conditions	Yield
With iron(II) chloride In toluene at 170℃; for 10h; Inert atmosphere;	55%

(vinyl)trimethoxylsilane (2768-02-7) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → 2,2-dimethoxy-2-phenyl-1-(2-(2-(trimethoxysilyl)ethyl)phenyl)ethane-1-one

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; triphenylphosphine In toluene for 48h; Inert atmosphere; Reflux;	38%

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → Perbenzoic acid (93-59-4)

Conditions	Yield
With oxygen In methanol Product distribution;	13%

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + p-toluenesulfonic acid monohydrate (6192-52-5) → benzil (134-81-6)

Conditions	Yield
In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol	1%

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → benzoyl radical (2652-65-5) + α,α'-dimethoxybenzyl radical (66822-20-6)

Conditions	Yield
In water; acetonitrile at 20℃; Quantum yield; Irradiation;
With sodium dodecyl-sulfate In water Micellar solution; Photolysis;
Photolysis;
UV-irradiation; Schlenk technique;

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → benzoic acid methyl ester (93-58-3) + methane (34557-54-5) + 1,2-diphenyl-1,1,2,2-tetramethoxyethane (39787-30-9) + methyl 4-Benzoylbenzoate (6158-54-9) + acetophenone (98-86-2) + benzil (134-81-6)

Conditions	Yield
In acetonitrile Product distribution; Ambient temperature; Irradiation; other photolysis conditions, pulse laser photolyse;

carbon tetrabromide (558-13-4) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → HBr

Conditions	Yield
In water; acetonitrile at 20℃; Quantum yield; Irradiation;

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → benzoic acid methyl ester (93-58-3) + 1,2-diphenyl-1,1,2,2-tetramethoxyethane (39787-30-9) + benzaldehyde (100-52-7) + acetophenone (98-86-2) + benzil (134-81-6) + benzoic acid (65-85-0) + CH3OH, CH4

Conditions	Yield
With disodium hydrogenphosphate In water; isopropyl alcohol Quantum yield; Irradiation; laser photolysis; other solvents;

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + poly(tetrafluoroethylene oxide-co-difluoromethylene oxide)α,ω-bis[-O-CO-NH-CH2CH2-O-CO-C(=CH2)-CH3] → poly(tetrafluoroethylene oxide-co-difluoromethylene oxide)α,ω-bis[-O-CO-NH-CH2CH2-O-CO-C(=CH2)-CH3]-2,2-dimethoxy-2-phenylacetophenone crosslinked

Conditions	Yield
In various solvent(s) for 10h; UV-irradiation;

C35H48F2O6*CF3O3S(1-)*Li(1+) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → C35H48F2O6*C16H16O3*CF3O3S(1-)*Li(1+)

Conditions	Yield
In dichloromethane at 20℃; for 24h;

hexamethylene glycol diacrylate (13048-33-4) + 2,2-dimethoxy-2-phenylacetophenone (24650-42-8) → polymer, living radical photopolymerization; monomer(s): 1,6-hexanediol diacrylate; 2,2-dimethoxy-2-phenylacetophenone

Conditions	Yield
UV-irradiation;

2,2-dimethoxy-2-phenylacetophenone (24650-42-8) + tris(diethyldithiocarbamato)iron(III) + methacrylic acid methyl ester (80-62-6) → dtc/DPMA terminated poly(methylmethacrylate) obtained by photo atom transfer radical polymerization of monomer, Mn = 10600-11200; monomer(s): methyl methacrylate; ferric tri(N,N-diethyldithiocarbamate); 2,2-dimethoxy-2-phenylacetophenone

Conditions	Yield
In toluene at 20℃; Kinetics; Further Variations:; Reagents; Photolysis;

Upstream product

• 24650-17-7 1H-[1,2,3]TRIAZOLE-4-CARBOXYLIC ACID HYDRAZIDE 
• 24650-10-0 2-[(4-aminocyclohexyl)methyl]cyclohexylamine 
• 24649-84-1 5-oxo-N-1H-1,2,4-triazol-3-ylpyrrolidine-2-carboxamide 
• 24649-67-0 9-(alpha-D-arabinofuranosyl)-9H-purine-2,6-diamine 
• 24649-37-4 3-methoxy-17-(prop-2-yn-1-yl)estra-1,3,5(10)-trien-17-ol 
• 24649-36-3 2β-Methoxy-5α-cholestan-19-oic acid methyl ester 
• 24649-22-7 3-Chloro-1-methoxyisoquinoline 
• 24648-61-1 5-[(1H-imidazol-2-ylsulfanyl)methyl]pyrimidine-2,4(1H,3H)-dione 
• 24648-52-0 N-carboxymethylisatoic anhydride 
• 24648-33-7 2,4,6-TRIMETHYL-1,3,6-HEPTATRIENE 
• 24648-13-3 1,3-Benzodithiole,2-(1,3-benzodithiol-2-ylidene)- 
• 24647-86-7 dimethyl 3-bromothiophene-2,4-dicarboxylate 
• 24647-85-6 methyl 4-bromo-2,5-diiodothiophene-3-carboxylate 
• 24647-84-5 methyl 4-bromo-5-iodothiophene-3-carboxylate 

Downstream Products

• 2465-05-6 Lanosta-7,9(11),24-trien-3β-ol acetate 
• 24650-63-3 uranium bicarbonate 
• 246509-60-4 2-Propen-1-amine,N-[(3-methoxyphenyl)methylene]-,[N(E)]-(9CI) 
• 246509-61-5 2-Propen-1-amine,N-[(2-methoxyphenyl)methylene]-,[N(E)]-(9CI) 
• 246510-69-0 (3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE 
• 2465-11-4 (22E)-5α-Ergosta-7,22-dien-3β-ol 
• 246511-74-0 3-Hexanone, 2-hydroxy-5-methyl- (9CI) 
• 246512-44-7 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide 
• 246514-65-8 {1-[2-(4-cyanoanilino)-2-oxoethyl]cyclopentyl}acetic acid 
• 246516-15-4 1-CARBOXYPENTYL-2,3,3-TRIMETHYLINDOLENIUM-5-SULFATE, POTASSIUM SALT 
• 246517-72-6 1,3,3-TRIMETHYL-2-((E)-2-(2-PHENYL-3-[(E)-2-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOPENTEN-1-YL)ETHENYL)-3H-INDOLIUM TETRAFLUOROBORATE 
• 246517-73-7 1,3,3-TRIMETHYL-2-((E)-2-(2-PHENYL-3-[(E)-2-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL)ETHENYL)-3H-INDOLIUM TETRAFLUOROBORATE 
• 246517-75-9 2-((E)-2-(2-(DIMETHYLAMINO)-3-[(E)-2-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL)ETHENYL)-1,3,3-TRIMETHYL-3H-INDOLIUM TETRAFLUOROBORATE 
• 24652-51-5 3-Penten-2-ol,3-methyl-, (3E)- 

Recommend Products

• 67-56-1  methanol 
• 501-65-5  diphenyl acetylene 
• 93-58-3  benzoic acid methyl ester 
• 39787-30-9  1,2-diphenyl-1,1,2,2-tetramethoxyethane 
• 134-81-6  benzil 
• 100-52-7  benzaldehyde 
• 98-86-2  acetophenone 
• 65-85-0  benzoic acid 
• 6192-52-5  p-toluenesulfonic acid monohydrate 
• 119-53-9  2-hydroxy-2-phenylacetophenone 
• 1151886-47-3  C₂₄H₃₄O₆Si 
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• 1485-70-7  N-benzylbenzamide 
• 100-46-9  benzylamine