[ CAS No. 13031-43-1 ] {[proInfo.proName]}

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2D 3D

Structure of 13031-43-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 13031-43-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13031-43-1 ]

SDS Specification

Alternatived Products of [ 13031-43-1 ]

Product Details of [ 13031-43-1 ]

CAS No. :	13031-43-1	MDL No. :	MFCD00017229
Formula :	C₁₀H₁₀O₃	Boiling Point :	No data available
Linear Structure Formula :	CH₃COOC₆H₄COCH₃	InChI Key :	SMIOEQSLJNNKQF-UHFFFAOYSA-N
M.W :	178.18	Pubchem ID :	83063
Synonyms :		Chemical Name :	4-Acetoxyacetophenone

Calculated chemistry of [ 13031-43-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.14
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	1.81
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	1.74

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.9
Solubility :	2.24 mg/ml ; 0.0126 mol/l
Class :	Very soluble
Log S (Ali) :	-1.8
Solubility :	2.82 mg/ml ; 0.0158 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.81
Solubility :	0.278 mg/ml ; 0.00156 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 13031-43-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13031-43-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 13031-43-1 ]
Downstream synthetic route of [ 13031-43-1 ]

[ 13031-43-1 ] Synthesis Path-Upstream 1~1

1
[ 13031-43-1 ]
[ 32136-81-5 ]

Reference： [1] Helvetica Chimica Acta, 1994, vol. 77, p. 1595 - 1610

Yield	Reaction Conditions	Operation in experiment
72%	With tert.-butylnitrite; N-hydroxyphthalimide; In acetonitrile; at 80℃; for 24h;Schlenk technique;	into a 25mL Schlenk reaction tube added NHPI 1.0equivalent, dried in vacuum for 15 minutes, put on an oxygen sphere, under the oxygen atmosphere followed by adding acetonitrile 1mL, tert-butyl nitrite 2.0 equiv., P-acetoxyethyl benzene 0.5mmol, on the reaction tube add Poly tetra-fluoroethylene plug into the oil bath after the pot, and carry on reaction at 80 C for 24 h. After completion of the reaction, the solvent acetonitrile has been removed by concentration under reduced pressure, column chromatography, the eluent is petroleum ether / ethyl acetate (nu: nu = 10: 1), and then obtained 4-acetoxyacetophenone. Yield 72%, white solid;
69%	With pyridine; dipotassium peroxodisulfate; oxygen; In acetonitrile; at 80℃; under 760.051 Torr; for 16h;Green chemistry;	General procedure: Ethylbenzene (3a) (0.0531 g, 0.5 mmol), K2S2O8 (0.2703 g, 1.0 mmol), pyridine (0.0158 g, 0.2 mmol) and CH3CN (1.0 mL) were added to an oven-dried pressure vessel with a magnetic stir bar. Then the pressure vessel was filled with dioxygen and the reaction mixture was stirred at 80 C for 16 hours (oil bath). After the completion of the reaction, the solvent was evaporated and the reaction mixture was purified with column chromatography (eluenet: ethyl acetate/PE = 1/10) to give acetophenone (4a) (0.0535 g yield 89%).
10%	With (2,2?-bipyridine)Zn(CF3)2; zinc diacetate; copper(l) cyanide; zinc trifluoromethanesulfonate; N-fluorobis(benzenesulfon)imide; at 20℃; for 24h;Sealed tube; Glovebox; Inert atmosphere;	To a dried sealed tube (10 mL) equipped with a Teflon septum and a magneticstirring bar in a glove box were added successively CuCN (1.8 mg, 0.02 mmol), NFSI(189 mg, 0.60 mmol), (bpy)Zn(CF3)2 (144 mg, 0.40 mmol), Zn(OTf)2 (36 mg, 0.1 mmol)and Zn(OAc)2 (18 mg, 0.1 mmol). The solution of 4-ethylphenyl acetate (3a, 33mg,0.20 mmol) in PhCF3 (4.0 mL) was added into the tube. The reaction mixture wasstirred at room temperature for 24 h under air. The resulting mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residuewas purified by column chromatography on silica gel with a gradient eluent ofpetroleum ether and ethyl acetate to give 4a-O (3.6 mg, 10%).

Yield	Reaction Conditions	Operation in experiment
	With bromine; triethyl phosphite; In chloroform; nitrogen; acetic acid; isopropyl alcohol;	(a) alpha-Brom-4-acetoxyacetophenone There was added to a solution of 17.8 kg of p-acetoxy acetophenone in 90 liters of dry chloroform a solution of 9.2 kg of bromine in 20 liters of chloroform with stirring in a nitrogen stream within 3 hours. After the HBr formed was completely driven out by nitrogen, there were added 0.37 kg of glacial acetic acid and 1 kg of triethyl phosphite and stirring continued for 1 hour at 20 C. and for another 1/2 hour at reflux temperature. Then it was evaporated in a vacuum and the residue dissolved in isopropanol. After 8 hours the mixture was filtered with suction and dried at 40 C. in a vacuum. Yield: 20.8 kg=81% of Theory; M.P. 68 C.; DC (solvent:chloroform): 1 HF, no side spots.
	With bromine; In dichloromethane; at 0 - 20℃;	Preparation of Compound I To a solution of 4-acetoxyacetophenone (1.0 eq) in dichloromethane on an ice bath was added bromine (1.05 eq). The bromine was added slowly at 0 C. The ice bath was removed and stirring continued at the ambient temperature until the reaction was complete (monitored by HPLC). The reaction mixture was concentrated in vacuum to provide 4-acetoxy-alpha-bromoacetophenone that was used without further purification.
	With pyridinium hydrobromide perbromide; In 1,4-dioxane; for 5h;	Pyridinium bromide perbromide (33.6g, 0.105 mole) was added to a solution of 4- acetylphenyl acetate (17.8 g, 0.1 mole) in dioxane (100 mL). The heterogeneous mixture was stirred for 5 hours. During the course of the reaction the intensity of the red color decreased and a white solid was formed. The reaction mixture was diluted with ether (200 mL) and washed with water (3X100 mL), brine (75 mL), dried (MgS04) and removed in vacuo to give the desired product as an oil, which solidified upon standing at room temperature (26.0 g). This product was used in the next transformation without further purification.

Yield	Reaction Conditions	Operation in experiment
> 99%Chromat.	With borane-ammonia complex; In methanol; water; at 20℃; for 0.0833333h;	General procedure: mpg-C3N4/Pd (4 mg) and the ketone or aldehyde (0.35 mmol)were suspended in methanol/water mixture (2 mL, 1:1) in apressure tube. Subsequently, AB (0.75 mmol) was addedand the solution was magnetically stirred for 2 (for aldehydes)or 5 min (for ketones) at room temperature. Aftercompletion of the reaction, the catalyst was filtered andwashed with methanol for further use. The solvent wasremoved under the reduced pressure. The yield of each alcoholwas determined by gas chromatography-mass spectrometry(GC-MS).
1440 g	With 5%-palladium/activated carbon; hydrogen; In toluene; at 15 - 20℃; under 6000.6 Torr;Large scale;	Put 2880g of toluene, 1440g of p-acetoxyacetophenone (obtained in Example 1), and 72g of Pd / C (50% water content, 5% Pd on dry basis) into a 5L pressure reactor, followed by nitrogen, hydrogen After the replacement, the internal temperature was controlled at 15 to 20 C, and the reaction was stirred under a hydrogen pressure of 8 bar.After the reaction, Pd / C was recovered by filtration, the solvent was recovered by distillation of the filtrate, and the concentrate was further distilled under reduced pressure to obtain 1440 g of 1- (4-acetoxyphenyl) ethanol. The HPLC purity was 99.0%.

Yield	Reaction Conditions	Operation in experiment
95%	With graphite oxide; In dichloromethane; at 30℃; for 1h;Green chemistry;	General procedure: To a solution of alcohols or phenols (3 mmol) and Ac2O (4.5 mmol; 9 mmol for dihydroxybenzenes) in CH3CN or CH2Cl2(2 mL) in a round-bottom flask was added GO (5 wt% of alcohols orphenols). The mixture was stirred at 20 C and the progress of the reaction was monitored by thin layer chromatography (TLC) analysis. After the completion of the reaction, the catalyst was filtered and washed with ethyl acetate (20 mL x 2). The filtrate was combined and washed with 15 mL of saturated sodium carbonate. The organic phase was dried over Na2SO4 and evaporated in vacuo to obtain the desired products. To determine the catalytic activity of Mn and K, we added MnO2, MnSO4 or KCl in the reaction between2-phenylethanol with Ac2O instead of GO and the yields of the corresponding ester (determined by 1H NMR) were listed in Table S1.
	With sulfuric acid; for 3h;Reflux;	General procedure: The suitable hydroxyacetophenone and acetic anhydride were refluxed with 2 drops concentrated sulfuric acid for 3 h.The reaction was checked using TLC. The reaction mixturewas poured into ice-water. The crystalline raw product was filtered and recrystallized from ethanol.
	With potassium carbonate; In dichloromethane; at 20℃; for 24h;	General procedure: Ac2O (0.6 mL, 6 mmol) was added to a mixture of phenol (0.47 g, 5mmol), and K2CO3 (1.35 g, 10 mmol) in CH2Cl2 (25 mL). The mixture was stirred for 24 h at r.t. The resulting mixture was washed several times with H2O. The organic phase was dried (anhyd Na2SO4) and then evaporated under reduced pressure. Pure phenyl acetate was obtained in 95% yield (120 mg) after column chromatography.

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Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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	With bromine; In ethyl acetate; at 50℃; for 0.0216667h;Sealed tube;	1, the preparation of raw materials:100 mL of a 4-acetoxyacetophenone ethyl acetate solution having a mass concentration of 16.6%Into the container, stirring to mix evenly sealed.Then, 200 mL of a bromine ethyl acetate solution having a mass concentration of 11.6%Placed in another container, sealed.2. With the apparatus of the present invention, Fig. 2,Follow the steps below:(1) The ethyl acetate solution containing 4-acetoxyacetophenone in the raw material tank 1 was passed through a metering pump 3Corning Microchannel Reactor 7,The ethyl acetate solution of the bromine in the raw material tank 2 is passed through the metering pump 4 into the Corning microchannel reactor 7;(2) Setting the flow rates of the ethyl acetate solution of the metering pump 3 and the metering pump 4 controlling the 4-acetoxyacetophenone:15 mL / min,The flow rate of the bromine-controlled ethyl acetate solution was 28.8 mL / min,The molar ratio of 4-acetoxyacetophenone to bromine was 1: 1.5,Set the heat exchanger temperature of 50 ;(3) the reaction channelThrough the stop valves 5 and 6 to prevent the back flow of materials;(4) After the mixing reaction in the Corning microchannel reactor 7, the reaction time is 1.3 min,The brominated product is continuously withdrawn and collected in a collection tank 8, The product was analyzed by LC.3. The purity of organic bromide in the reaction product was 80.5%Yield 72%.
	With bromine; In chloroform; for 3h;	General procedure: The suitable aceticacid acetylphenylester derivative and bromine were separately dissolved in chloroform and the reaction was carried out by dropping bromine for 3 h. When the reaction conclude, solvent was evaporated and viscous liquid substance was obtained.

Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H226	Flammable liquid and vapour
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H228	Flammable solid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 13031-43-1 ] {[proInfo.proName]}

Quality Control of [ 13031-43-1 ]

Related Doc. of [ 13031-43-1 ]

Product Details of [ 13031-43-1 ]

Calculated chemistry of [ 13031-43-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13031-43-1 ]

Application In Synthesis of [ 13031-43-1 ]

[ 13031-43-1 ] Synthesis Path-Upstream 1~1

[ 13031-43-1 ] Synthesis Path-Downstream 1~10

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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