[ CAS No. 490-78-8 ] {[proInfo.proName]}

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Quality Control of [ 490-78-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 490-78-8 ]

SDS Specification

Alternatived Products of [ 490-78-8 ]

Product Details of [ 490-78-8 ]

CAS No. :	490-78-8	MDL No. :	MFCD00002343
Formula :	C₈H₈O₃	Boiling Point :	-
Linear Structure Formula :	C₆H₃(OH)₂(COCH₃)	InChI Key :	WLDWSGZHNBANIO-UHFFFAOYSA-N
M.W :	152.15	Pubchem ID :	10279
Synonyms :		Chemical Name :	1-(2,5-Dihydroxyphenyl)ethanone

Calculated chemistry of [ 490-78-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.68
TPSA :	57.53 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	1.65
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.19
Consensus Log Po/w :	1.21

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.05 mg/ml ; 0.00691 mol/l
Class :	Soluble
Log S (Ali) :	-2.47
Solubility :	0.514 mg/ml ; 0.00338 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.57
Solubility :	4.13 mg/ml ; 0.0272 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.04

Safety of [ 490-78-8 ]

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

Application In Synthesis of [ 490-78-8 ]

* 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 [ 490-78-8 ]
Downstream synthetic route of [ 490-78-8 ]

[ 490-78-8 ] Synthesis Path-Upstream 1~2

1
[ 490-78-8 ]
[ 26964-24-9 ]

Reference： [1] Journal of the Chinese Chemical Society, 2004, vol. 51, # 6, p. 1389 - 1394

2
[ 490-78-8 ]
[ 869478-09-1 ]

Reference： [1] Patent: CN107188865, 2017, A,

[ 490-78-8 ] Synthesis Path-Downstream 1~6

1
[ 100-44-7 ]
[ 490-78-8 ]
[ 30992-63-3 ]

Yield	Reaction Conditions	Operation in experiment
81.3%	With potassium iodide; In acetone; for 6h;Reflux;	2 ', 5'-hydroxyacetophenone (7.60g, 0.05mol),Anhydrous potassium carbonate (8.00g, 0.06 mol),Potassium iodide (1.00g, 0.006mol),100mL of acetone is placed in a 250mL eggplant-shaped bottle.Stir at room temperature.Benzyl chloride (7.87 g, 0.06 mol) was diluted with 10 mL of acetone and dropped into the reaction solution at a constant rate. The addition was completed in about 10 minutes. The reaction was heated at reflux for 6 h and the reaction was monitored by TLC. After the reaction was completed, it was cooled to room temperature and the organic solvent was distilled off under reduced pressure to give yellow crystals.Recrystallization from 50 mL of ethanol gave 9.84 g of yellow crystals with a yield of 81.3%.
81.3%	With potassium carbonate; potassium iodide; In acetone; for 6h;Reflux;	The 2',5'-dihydroxyacetophenone(7.60g, 0.05mol),Anhydrous potassium carbonate (8.00g, 0.06mol), potassium iodide (1.00g, 0.006mol),100 mL of acetone was placed in a 250 mL eggplant-shaped flask and stirred at room temperature.Benzyl chloride (7.87g, 0.06mol) was diluted with 10mL of acetone and dropped into the reaction solution at a constant rate.About 10 minutes after the completion of the drop. The reaction was heated at reflux for 6 h and the reaction was monitored by TLC.After the reaction was completed, it was cooled to room temperature and the organic solvent was distilled off under reduced pressure to give yellow crystals.Recrystallization from 50 mL of ethanol gave 9.84 g of yellow crystals with a yield of 81.3%
80.7%	With potassium carbonate; In acetone; at 56 - 60℃; for 5h;	General procedure: In a 250 ml round-bottomed flask were placed 2?,4?-dihydroxyacetophenone or 2?,5?-dihydroxyacetophenone (0.10 mol), benzylchloride(0.105 mol), potassium iodide (0.01 mol), anhydrous potassium carbonate (1 mol) and 100 ml dry acetone. The mixture was refluxed for 5 h at 56-60 C in oil bath. After reaction was finished, the reaction liquid was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to obtain the crude. The solid was recrystallized from 100 ml ethanol to obtain 1.

Reference： [1]Journal of Chemical Research, Miniprint,1981,p. 2564 - 2572
[2]Patent: CN107857748,2018,A .Location in patent: Paragraph 0036; 0044; 0045
[3]Patent: CN107935972,2018,A .Location in patent: Paragraph 0036; 0037; 0038
[4]Bioorganic Chemistry,2020,vol. 95
[5]Journal of the Chemical Society,1935,p. 868

2
[ 100-39-0 ]
[ 490-78-8 ]
[ 30992-63-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 18-crown-6 ether; potassium carbonate; potassium iodide; In toluene; at 115℃; for 14h;	The second alternate way consists in making at first the protection of the OH function with a benzylic group by involving the same conditions as for the previous O-alkylation reaction to furnish the acetophenone derivative (1-6) in a very good yield (95%). To form the product (1- 7), beforehand synthesized by the other methodology, acetophenone derivative (1-6) was submitted to VilsmeierHaack reaction using standard conditions (70%). Knoevenagel condensation of the resulting product (1-7) with diethyl malonate provided in an ultimate stage the expected diester (1-8) in high yield (94%). In view of these results (Scheme 2), we can notice that in priori both ways can be used to synthesize the intermediate (1-7) in an overall yield of 42% and 66%, respectively, from the dihydroxy-acetophenone (1-4) as the raw material; with however the second way more effective in term of yield.
88.3%	With sodium hydrogencarbonate; In ethanol; at 0 - 10℃; for 3.33333h;	[0168] 152 g (1.0 mol) of 2,5-dihydroxy acetophenone was added to a 1L three-necked flask. 400 mL of absolute ethanol was added, stirred for dissolution. 92.4 g (1.1 mol) of sodium bicarbonate was added at room temperature and stirred for 5 minutes. The temperature of the reaction mixture was kept at 0-10 C. 180 g (1.05 mol) of benzyl bromide was added dropwise, and the addition was completed within 20 minutes. At this temperature, the reaction was continued with stirring for 3 hours, and thin layer detection showed that the raw material 2,5-dihydroxyacetophenone was reacted completely. The solvent was removed under reduced pressure. The residue was dissolved with 400 mL of dichloromethane, and washed with saturated citric acid aqueous solution 3 times (3150 mL). The the dichloromethane solution was dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration. Dichloromethane was removed from the solution under reduced pressure. The residue was dissolved in 300 mL of absolute ethanol which is cooled and crystallized to obtain 213.7 g of 2-hydroxy-5-benzyloxy acetophenone as a white solid with a yield of 88.3%. The chemical purity was 99.0% (HPLC).
75.6%	With potassium carbonate; In 4-methyl-2-pentanone; at 60℃; for 20h;	1-[2-hydroxy-5-(phenylmethoxy)-phenyl]-ethanone: 20 kg (131.4 mol) 2-acetyl-hydroquinone 6a are dissolved in 150 l methylisobutylketone and combined with 19.98 kg (144.6 mol) potassium carbonate. At 60 C., 22.48 kg (131.5 mol) benzyl bromide are added. The reaction mixture is stirred for 20 hours at 60 C. The reaction mixture is cooled to 25 C. and the solid is filtered off. The filtrate is washed twice with a solution of 0.96 kg (11.8 mol) sodium hydroxide solution (50%) and 60 l water at 25 C. The methylisobutylketone is largely distilled off in vacuo, and the residue is dissolved in 80 l methanol at 60 C. The solution is cooled to 0 C. and stirred for 1 hour at this temperature to complete the crystallisation. Yield (5a): 24.07 kg (75.6%), chemical purity according to HPLC: 99.2%.

75.6%	With potassium carbonate; In 4-methyl-2-pentanone; at 60℃; for 20h;Industry scale;	1-[2-hydroxy-5-(phenylmethoxy)-phenyl]-ethanone: 20 kg (131.4 mol) 2-acetyl-hydroquinone 6a are dissolved in 150 L methylisobutylketone and combined with 19.98 kg (144.6 mol) potassium carbonate. At 60 C., 22.48 kg (131.5 mol) benzyl bromide are added. The reaction mixture is stirred for 20 hours at 60 C. The reaction mixture is cooled to 25 C. and the solid is filtered off. The filtrate is washed twice with a solution of 0.96 kg (11.8 mol) sodium hydroxide solution (50%) and 60 L water at 25 C. The methylisobutylketone is substantially distilled off in vacuo, and the residue is dissolved in 80 L methanol at 60 C. The solution is cooled to 0 C. and stirred for 1 hour at this temperature to complete the crystallisation.Yield (5a): 24.07 kg (75.6%), chemical purity according to HPLC: 99.2%.
8 g (82%)	With potassium carbonate; In acetone;	EXAMPLE 9 Stage A: 5-Benzyloxy-2-hydroxyacetophenone A mixture of 2,5-dihydroxyacetophenone (6.10 g = 40 mM), benzyl bromide (5 ml = 42 mM) and anhydrous potassium carbonate (5,6 g = 40 mM in anhydrous acetone (120 ml)) is heated under reflux for 5 hours. Then, the mixture is concentrated under reduced pressure, the residue is taken up with 1N HCl (120 ml) and extracted with ethyl ether. The combined extracts are washed with water and with a saturated ammonium sulfate solution, anhydrated (Na2SO4) and concentrated to give a crude solid compound that is then purified by flash-chromatography (4:1, n-hexane: ethyl acetate as the eluent) to give 8 g (82%) of a yellow solid, m.p. 63-65C.
49 g	With potassium carbonate; In acetone; for 16h;Reflux;	1000 ml three-neck bottle , the compound 1 - 4 (44 g, 290 mmol), potassium carbonate (44 g, 319 mmol) dissolved in acetone (750 ml), heated to 60 C, continue adding benzyl bromide (57.7 g, 304.5 mmol), reflux reaction 16 h. Cooling the reaction liquid to room temperature, the solid in filtering system, concentrated, continue adding ethyl acetate (400 ml), sequentially for cold aqueous solution of sodium hydroxide (1 M, 50 ml), water (200 ml) and saturated salt water (200 ml).The organic phase drying, filtering, concentrated and methanol recrystallization to obtain a yellow solid product 49 g.

Reference： [1]Patent: WO2018/156459,2018,A1 .Location in patent: Page/Page column 22; 23
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 249 - 266
[3]Patent: EP3556435,2019,A1 .Location in patent: Paragraph 0168
[4]Patent: US2007/88160,2007,A1 .Location in patent: Page/Page column 10-11
[5]Patent: US2010/22770,2010,A1 .Location in patent: Page/Page column 5-6
[6]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1410 - 1414
[7]Journal of Medicinal Chemistry,2008,vol. 51,p. 3326 - 3329
[8]Arzneimittel-Forschung/Drug Research,1984,vol. 34,p. 843 - 849
[9]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 115 - 120
[10]Patent: EP401517,1990,A1
[11]Patent: CN107188865,2017,A .Location in patent: Paragraph 0051; 0056; 0057

3
[ 490-78-8 ]
PhCH₂X [ No CAS ]
[ 30992-63-3 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 2041 - 2055

4
[ 490-78-8 ]
[ 30992-63-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 3039 - 3048

5
[ 100-39-0 ]
[ 584-08-7 ]
[ 490-78-8 ]
[ 30992-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide; hexane; ethyl acetate; acetone;	PREPARATION 1 5-Benzyloxy-2-hydroxyacetophenone To 2,5-dihydroxyacetophenone (30 g, 0.197 mol) dissolved in 600 ml acetone was added benzyl bromide (24.64 ml, 1.05 equiv) and K2 CO3 (68.0 g, 0.492 mol). The mixture was heated at reflux under N2 for 2 days, then cooled to room temperature, filtered and stripped of solvent in vacuo. The residue was taken up in 500 ml ethyl acetate, washed 3* with ice cold IN NaOH, 2* with H2 O and 2* with brine, dried (Na2 SO4), stripped to solids, and chromatographed on silica gel using 9:1 hexane:ethyl acetate as eluant to yield 35 g of purified title product. A portion was recrystallized as needles from hexane; mp 68-70 C.; Anal. C 74.37, H 5.69, calcd. C 74.36, H 5.82, 1 H-NMR (300 MHz, CDCl3) delta (ppm) 2.6 (s, 3H), 5.05 (s, 2 H), 6.9 (d, 1H), 7.1-7.45 (m, 7H), 11.85 (s, 1H).

Reference： [1]Patent: US5248685,1993,A

6
[ 1668-54-8 ]
[ 490-78-8 ]
[ 1465740-20-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5968 - 5970

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Isomers

Technical Information

? Acidity of Phenols ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? 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 ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? 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 ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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. 490-78-8 ] {[proInfo.proName]}

Quality Control of [ 490-78-8 ]

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Medicinal Chemistry

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[ 490-78-8 ] Synthesis Path-Upstream 1~2

[ 490-78-8 ] Synthesis Path-Downstream 1~6

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Aryls

Ketones

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[ 490-78-8 ]