947-19-3

Basic information

• Product Name: 1-Hydroxycyclohexyl phenyl ketone
• Synonyms: (1-hydroxycyclohexyl)phenyl-methanon;(1-hydroxycyclohexyl)phenyl-Methanone;alpha-hydroxycyclohexylphenylketone;photoinitiator184;A-HYDROXYCYCLOHEXYLPHENYLKETONE;1-HYDROXYCYCLOHEXYL PHENYL KETONE;1-HYDROXY-1-CYCLOHEXYL PHENYL KETONE;1-BENZOYLCYCLOHEXANOL
• CAS NO: 947-19-3
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26
• EINECS: 213-426-9
• Product Categories: Industrial/Fine Chemicals;Functional Materials;Photopolymerization Initiators;Acetophenone;Organic Photoinitiators;Polymerization Initiators;Other Products
• Mol File: 947-19-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 47-50 °C(lit.)
• Boiling Point: 175 °C15 mm Hg(lit.)
• Flash Point: >150°C
• Appearance: White crystalline powder
• Density: 1,17 g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5170 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 13.23±0.20(Predicted)
• Water Solubility: Slightly soluble in water (1108 mg/L at 25°C). Soluble in acetone, butyl acetate, methanol and toluene.
• BRN: 2330973
• CAS DataBase Reference: 1-Hydroxycyclohexyl phenyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxycyclohexyl phenyl ketone(947-19-3)
• EPA Substance Registry System: 1-Hydroxycyclohexyl phenyl ketone(947-19-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25
• TSCA: Yes
• Hazardous Substances Data: 947-19-3(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

1-Hydroxycyclohexyl phenyl ketone is used as photoinitiator in UV-radiation-curable technologies which are used in various applications and industry branches such as printing and packaging, coatings, furniture and flooring and adhesives.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 3084, 1967 DOI: 10.1021/ja00988a072

General Description

1-Hydroxycyclohexyl phenyl ketone is a photoinitiator (PI) molecule that can be used in chain transfer polymerization. PI can be incorporated in the polymeric matrix by the addition of a chromophore as a pendant group. It may be used as a component that facilitates UV curing and also as a base material in the formation of the block and grafted copolymers.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C25H30O3/c26-23(19-11-3-5-13-21(19)24(27)15-7-1-8-16-24)20-12-4-6-14-22(20)25(28)17-9-2-10-18-25/h3-6,11-14,27-28H,1-2,7-10,15-18H2

Synthetic route

(1-chlorocyclohexyl)(phenyl)methanone (1135-71-3) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In water at 90℃; for 4.5h; Reagent/catalyst;	99%
With tetra(n-butyl)ammonium hydroxide In water; 1,2-dichloro-ethane at 35℃; for 1.5h; Solvent; Temperature; Reagent/catalyst;	93%
With sodium hydroxide

Cyclohexyl phenyl ketone (712-50-5) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With oxygen; caesium carbonate; triethyl phosphite In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 72h; Schlenk technique;	96%
With tetrabutylammomium bromide; sodium hydroxide In tetrachloromethane at 80 - 90℃; for 12h;	90.2%
With di-tert-butyl peroxide In dichloromethane at 50℃; Temperature; Sonication;	86.62%

1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) + chlorobenzene (108-90-7) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With sodium In tetrahydrofuran at -5 - 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	95%

(1-bromocyclohexyl)(phenyl)methanone (7500-66-5) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In water; 1,2-dichloro-ethane at 35℃; for 1.5h;	90%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 80℃; for 1h;	59%
Stage #1: (1-bromocyclohexyl)(phenyl)methanone With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 80℃; for 1h; Stage #2: With hydrogenchloride In water pH=3;	59%
Multi-step reaction with 2 steps 1: methanol. 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 2: aq. HCl View Scheme

1-trimethylsilanyloxycyclohexanecarbonitrile (24731-36-0) + phenylmagnesium bromide (100-58-3) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
In diethyl ether for 3h; Ambient temperature;	86.5%

α-(trimethylsiloxy)-1-cyclohexyl phenyl ketone (56345-98-3) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With sodium acetate for 2h; Ambient temperature;	86%

cyclohexanone (108-94-1) + Benzotrichlorid (98-07-7) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With magnesium In N,N-dimethyl-formamide at -20 - -10℃; for 2h; Inert atmosphere;	86%

1-(α-Bromobenzyl)cyclohexan-1-ol (801163-54-2) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Stage #1: 1-(α-Bromobenzyl)cyclohexan-1-ol With water at 100℃; for 1h; Stage #2: With dihydrogen peroxide for 6h; Cooling with ice; Irradiation;	65%

1-trimethylsilanyloxycyclohexanecarbonitrile (24731-36-0) + PhMgX → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
In diethyl ether	61%

1-cyclohexenyl(phenyl)methanone (17040-65-2) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Stage #1: 1-cyclohexenyl(phenyl)methanone With phenylsilane; oxygen; isopropyl alcohol; Mn(dpm)3 In 1,2-dichloro-ethane at 0 - 25℃; Stage #2: With triethyl phosphite In 1,2-dichloro-ethane	50%

benzoyltrimethylsilane (5908-41-8) + cyclohexanone (108-94-1) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran	35%

1-tetrahydropyran-2-yloxy-cyclohexanecarbonitrile (1206-23-1) + phenylmagnesium bromide → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) + phenylmagnesium bromide → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

2-methoxy-2-phenyl-1-oxa-spiro[2.5]octane (15817-28-4) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With hydrogenchloride
Multi-step reaction with 2 steps 1: petroleum ether 2: H2O / methanol View Scheme

(1-bromocyclohexyl)(phenyl)methanone (7500-66-5) → 1-phenyl-cyclohexanecarboxylic acid (1135-67-7) + 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With sodium hydroxide; toluene
With 1,4-dioxane; silver nitrate

(1-chlorocyclohexyl)(phenyl)methanone (1135-71-3) → 1-phenyl-cyclohexanecarboxylic acid (1135-67-7) + 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With sodium hydroxide; toluene
With 1,4-dioxane; silver nitrate

α-Hydroxycyclohexyl-phenyl-N-methylimin (92499-59-7) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With hydrogenchloride

benzoyl cyanide (613-90-1) + cyclohexanone (108-94-1) → 1-hydroxycyclohexyl phenyl ketone (947-19-3) + 1-cyanobenzyl benzoate (4242-46-0)

Conditions	Yield
With titanium(III) chloride; potassium carbonate; acetic acid 1) water, 2 h, r.t., 2) t-BuOH, 35 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate (31675-43-1) + cyclohexanone (108-94-1) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Yield given. Multistep reaction;

1-[(2-chloro-ethoxy)-methoxy-phenyl-methyl]-cyclohexanol (843-51-6) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With water In methanol

phenyllithium (591-51-5) + lithium-salt of/the/ 1-hydroxy-cyclohexanecarboxylic acid → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

tetrachloromethane (56-23-5) + diethyl ether (60-29-7) + (1-chlorocyclohexyl)(phenyl)methanone (1135-71-3) → 1-hydroxycyclohexyl phenyl ketone (947-19-3) + 1-phenyl-cyclohexane-carboxylic acid-(1)

1-trimethylsilanyloxycyclohexanecarbonitrile (24731-36-0) + phenylmagnesium chloride (100-59-4) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
In tetrahydrofuran

cyclohexanone (108-94-1) + 1--pyridium iodide → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran 2: tetrahydrofuran View Scheme

cyclohexanone (108-94-1) + 1.1'-dinitro-dicyclohexyl → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94.9 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / Ambient temperature 2: 86.5 percent / diethyl ether / 3 h / Ambient temperature View Scheme

cyclohexanone (108-94-1) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1. LDA / 1. THF, cyclohexane, -78 deg C, 30 min, 2a. 30 min, 2b. RT, overnight 2: 86 percent / aq. sodium acetate / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1 h / 60 °C 1.2: 8 h / Reflux 2.1: dihydrogen peroxide; hydrogen bromide / 1,2-dichloro-ethane / 8 h / 60 °C / Irradiation; Cooling with ice 3.1: water / 1 h / 100 °C 3.2: 6 h / Cooling with ice; Irradiation View Scheme

1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; hydrogen chloride View Scheme

2-phenyl-1-oxaspiro[2,5]octane (34877-64-0, 37545-92-9) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

Conditions	Yield
With oxygen; palladium diacetate; Bathocuproine In water at 100℃; for 48h;

(1-hydroxycyclohexyl)(benzene)methanol (1135-72-4) → 1-hydroxycyclohexyl phenyl ketone (947-19-3)

4-methyleneoxetan-2-one (674-82-8) + 1-hydroxycyclohexyl phenyl ketone (947-19-3) → 3-acetyl-5,5-pentamethylen-4-phenylfuran-2(5H)-one (1373648-45-3)

Conditions	Yield
With triethylamine	98%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + acetic anhydride (108-24-7) → 1-benzoylcyclohexyl acetate (4915-84-8)

Conditions	Yield
With pyridine at 20℃; Inert atmosphere;	95%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + pivaloyl chloride (3282-30-2) → 1-benzoylcyclohexyl pivalate (1196070-17-3)

Conditions	Yield
With pyridine at 25℃; Inert atmosphere;	93%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → 1-(α-Amino-benzyl)-cyclohexanol (102729-78-2)

Conditions	Yield
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; for 24h; chemoselective reaction;	88%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + methanesulfonyl chloride (124-63-0) → 1-benzoylcyclohexyl methanesulfonate (87456-65-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → (cyclohexylidenemethyl)benzene (1608-31-7) + Cyclohexyl phenyl ketone (712-50-5)

Conditions	Yield
With acetic acid; zinc at 60℃; for 4h;	A 5.3% B 83.3%
With acetic acid; zinc at 90℃; for 2h;	A 20.3% B 73%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + benzo[d]thiazol-2-yltriphenylphosphonium trifluoromethanesulfonate (116928-25-7) → (1-(benzo[d]thiazol-2-yloxy)cyclohexyl)(phenyl)methanone

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	83%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + pyruvoyl chloride (5704-66-5) → 1-benzoylcyclohexyl methyl oxalate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	83%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + 3-Cyclohexyliden-2-(diethoxyphosphoryl)-N,N-diphenyl-2-propenamid (150080-78-7) → 2-Cyclohexyliden-4,N,N-triphenyl-1-oxaspiro<4.5>dec-3-en-3-carboxamid

Conditions	Yield
With sodium hydride In toluene at 80℃; for 0.75h;	80%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → 1-cyclohexenyl(phenyl)methanone (17040-65-2)

Conditions	Yield
trifluorormethanesulfonic acid In dichloromethane for 16h; Ambient temperature;	79%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → 1-cyclohexenyl(phenyl)methanone (17040-65-2) + (4aS,9aR)-1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-one (1203-67-4)

Conditions	Yield
With sulfuric acid; hydroquinone In chloroform for 6h; Ambient temperature;	A 71% B 3.8%
With sulfuric acid; hydroquinone In chloroform for 6h; Ambient temperature;	A 71% B 3.8%

Ethyl bromodifluoroacetate (667-27-6) + 1-hydroxycyclohexyl phenyl ketone (947-19-3) → C17H20F2O4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate; silver fluoride; triphenylphosphine In hexane at 140℃; for 20h; Inert atmosphere; Sealed tube;	63%

1-hydroxycyclohexyl phenyl ketone (947-19-3) + phenylacetonitrile (140-29-4) → 3,4-diphenyl-1-oxa-spiro[4,5]dec-3-en-2-one

Conditions	Yield
With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;	62%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → Cyclohexyl phenyl ketone (712-50-5)

Conditions	Yield
With potassium acetate; L-proline In dimethyl sulfoxide at 100℃; for 10h; Temperature;	60%
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 2: diphenylsilane; zinc; nickel dichloride; magnesium chloride; 2-(2'-pyridyl)benzimidazole / N,N-dimethyl acetamide / 40 °C / Inert atmosphere; Schlenk technique View Scheme

para-bromotoluene (106-38-7) + 1-hydroxycyclohexyl phenyl ketone (947-19-3) → ((1R,2R)-1-Hydroxy-2-p-tolyl-cyclohexyl)-phenyl-methanone

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; caesium carbonate In o-xylene for 5h; Heating;	59%

carbon monoxide (201230-82-2) + 1-hydroxycyclohexyl phenyl ketone (947-19-3) + 1-cyclopropyl-1,3,3-trimethylurea → 1-benzoylcyclohexyl 4-(1,3,3-trimethylureido)butanoate

Conditions	Yield
With di(rhodium)tetracarbonyl dichloride; tris(pentafluorophenyl)phosphine In 1,2-dichloro-benzene at 130℃; under 760.051 Torr; for 96h; Glovebox;	56%

1-hydroxycyclohexyl phenyl ketone (947-19-3) → benzoic acid (65-85-0)

Conditions	Yield
With oxygen; acetic acid In water at 60℃; under 750.075 Torr; for 12h;	50%
With C59H45BFeN6O3; oxygen In benzene at 20℃; for 0.366667h; Inert atmosphere;	50 %Spectr.

1-hydroxycyclohexyl phenyl ketone (947-19-3) + tert-butyl 2-(bromomethyl)acrylate (53913-96-5) → C21H28O4

Conditions	Yield
Stage #1: 1-hydroxycyclohexyl phenyl ketone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.75h; Williamson Ether Synthesis; Inert atmosphere; Stage #2: tert-butyl 2-(bromomethyl)acrylate In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h; Williamson Ether Synthesis;	40%

Upstream product

• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 613-90-1 benzoyl cyanide 
• 108-94-1 cyclohexanone 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 5908-41-8 benzoyltrimethylsilane 
• 17040-65-2 1-cyclohexenyl(phenyl)methanone 
• 801163-54-2 1-(α-Bromobenzyl)cyclohexan-1-ol 
• 108-90-7 chlorobenzene 
• 100-52-7 benzaldehyde 
• 766-05-2 cyclohexane carbonitrile 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 98-07-7 Benzotrichlorid 
• 110-82-7 cyclohexane 

Downstream Products

• 2143-60-4 α-hydroxycyclohexyl radical 
• 2652-65-5 benzoyl radical 
• 15015-46-0 1--1-cyclohexanol 
• 712-50-5 Cyclohexyl phenyl ketone 
• 65-85-0 benzoic acid 
• 451-40-1 phenyl benzyl ketone 
• 4065-81-0 cyclohexen-1-ol 
• 108-94-1 cyclohexanone 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-52-7 benzaldehyde 
• 108-93-0 cyclohexanol 
• 17040-65-2 1-cyclohexenyl(phenyl)methanone 
• 7500-67-6 (1-benzoyloxy-cyclohexyl)-phenyl ketone 
• 412346-08-8 8,16-diphenyl-7,15-dioxa-dispiro[5.2.5.2]hexadecane-8,16-diol 

Relevant articles and documents

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Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

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Method for preparing alpha-hydroxy ketone photoinitiator in microreactor

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Preparation method of alpha-hydroxyketone photoinitiator

The invention provides a preparation method of an alpha-hydroxyketone photoinitiator. The preparation method comprises the steps of taking a ketone compound and a trihalomethyl-substituted benzene anda derivative thereof as raw materials, enabling the raw materials to react under the action of a polar solvent and a metal catalyst to form a halogenated intermediate in one step, and hydrolyzing theobtained product under the action of an alkali metal hydroxide aqueous solution and a phase transfer catalyst to obtain the alpha-hydroxyketone photoinitiator. The operation is simple, the reaction step is short, no Lewis acid catalyst is used in the reaction, the pollution is small, the catalyst can be recycled, by-products are less, the cost is low, and a variety of products can be produced bythe same method.

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Photocatalytic synthesis method of 1-hydroxyl cyclohexyl phenyl ketone compound and application thereof

A photocatalytic synthesis method of a 1-hydroxyl cyclohexyl phenyl ketone compound comprises the following steps that (a) 4-Ryl benzaldehyde and cyclohexane produce free radical reaction under the irradiation of an ultraviolet lamp to obtain 4-Ryl cyclohexyl phenyl ketone; (b) the 4-Ryl cyclohexyl phenyl ketone uses dimethyl sulfoxide as a solvent, uses hydrobromic acid as a bromine source, hydroxyl substitution is performed to obtain 1-hydroxyl cyclohexyl-(4-R phenyl) ketone, and the dimethyl sulfoxide is removed for recycle through distillation. A 1-hydroxyl cyclohexyl-(4-R phenyl) ketone coarse product is obtained through a crystallization method, and a 1-hydroxyl cyclohexyl-(4-R phenyl) ketone photoinitiator finished product is obtained through recrystallization. The synthesis methodhas the advantages that the synthesis steps of the method are simple, the preparation cost is low and no pollution is produced. The prepared cyclohexyl phenyl ketone compound is suitable for the efficient photoinitiator of UV light curing system, the product has better non-yellowing characteristic under the irradiation of an ultraviolet source, and popularization and development of a UV light curing technology are facilitated.

Ultrasonic preparation method for alpha-hydroxyketones

The invention relates to the technical field of organic synthesis, and concretely relates to an ultrasonic preparation method for alpha-hydroxyketones. Ketones and peroxide which are used as raw materials undergo an ultrasonic reaction in the presence of an organic solvent to prepare the alpha-hydroxyketones. The preparation method provided by the invention avoids the use of halogens with high toxicity and high risks in the reaction process to avoid the risk of the product not meeting the requirements of the regulations due to the introduction of the halogens in the reaction process, and alsohas the advantages of low cost of the overall process, shortening of the cycle of batch production, simplicity in process operation and easiness in achieving of large-scale production.