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89-84-9

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89-84-9 Usage

Chemical Properties

2,4-Dihydroxyacetophenone is yellow-brown to reddish-brown fine cryst. powder

Uses

Different sources of media describe the Uses of 89-84-9 differently. You can refer to the following data:
1. 2,4-Dihydroxyacetophenone is used as intermediate for pharmaceuticals.
2. Reagent for iron as a 10% alcoholic solution. A red color is obtained with ferric ions in slightly acid solution: Cooper, Ind. Eng. Chem. Anal. Ed. 9, 334 (1937).
3. 2'',4''-Dihydroxyacetophenone (cas# 89-84-9) is a compound useful in organic synthesis.

Preparation

Preparation by reaction of acetic acid on resorcinol,with zinc chloride (Nencki reaction) (94%)with boron trifluoridewith Amberlite IR-120 (a cation exchange resin, sulfonic acid type) (87%)with polyphosphoric acid (63%)with 70% perchloric acid (33%).

Definition

ChEBI: A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 428, 1948 DOI: 10.1021/ja01181a521

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. A severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 89-84-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 89-84:
(4*8)+(3*9)+(2*8)+(1*4)=79
79 % 10 = 9
So 89-84-9 is a valid CAS Registry Number.

89-84-9 Well-known Company Product Price

  • Brand
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  • Alfa Aesar

  • (A12066)  2',4'-Dihydroxyacetophenone, 98%   

  • 89-84-9

  • 50g

  • 397.0CNY

  • Detail
  • Alfa Aesar

  • (A12066)  2',4'-Dihydroxyacetophenone, 98%   

  • 89-84-9

  • 250g

  • 1574.0CNY

  • Detail

89-84-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2',4'-dihydroxyacetophenone

1.2 Other means of identification

Product number -
Other names 2,4-Dihydroxyacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:89-84-9 SDS

89-84-9Synthetic route

2-hydroxy-4-(methoxymethoxy)acetophenone
65490-08-6

2-hydroxy-4-(methoxymethoxy)acetophenone

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 70℃; for 0.75h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures;100%
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;90%
acetic acid
64-19-7

acetic acid

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 0.0333333h; microwave irradiation;98%
With iron(III) chloride for 0.0221667h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction;98%
With zinc(II) chloride Reflux;98%
2,4-diacetoxy acetophenone
72712-19-7

2,4-diacetoxy acetophenone

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With water; sodium acetate In ethanol for 5h; Reflux;98%
2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With acyltransferase from bacterium Pseudomonas sp.YGJ3 In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 18h; pH=7.5; Friedel-Crafts Acylation; Enzymatic reaction; regioselective reaction;97%
acetic acid 2-acetyl-5-methoxymethoxy-phenyl ester

acetic acid 2-acetyl-5-methoxymethoxy-phenyl ester

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;95%
1-(2,4-dihydroxy-phenyl)-ethanone oxime
6134-79-8

1-(2,4-dihydroxy-phenyl)-ethanone oxime

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With periodic acid at 20℃; for 0.0833333h;92%
sodium acetate
127-09-3

sodium acetate

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; acetic acid Inert atmosphere;91%
acetic anhydride
108-24-7

acetic anhydride

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride at 60℃; for 4h; Temperature; Large scale;90.6%
With PPA Reflux;68%
With phosphorus pentoxide; silica gel at 100℃; for 24h;65%
1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone
29682-12-0

1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With formic acid; sodium formate; palladium on activated charcoal In methanol for 1h; Product distribution; Heating; other aryl benzyl ethers;90%
With formic acid; sodium formate; palladium on activated charcoal In methanol for 1h; Heating;90%
acetic anhydride
108-24-7

acetic anhydride

recorcinol
108-46-3

recorcinol

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

2,4-diacetylresorcinol
2163-12-4

2,4-diacetylresorcinol

C

1-(5-acetyl-2,4-dihydroxyphenyl)-1-ethanone
2161-85-5

1-(5-acetyl-2,4-dihydroxyphenyl)-1-ethanone

Conditions
ConditionsYield
With zinc(II) chloride at 145 - 150℃; for 0.25h;A 2%
B 7%
C 90%
2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate for 0.0333333h; microwave irradiation;80%
4-allyloxy-2-hydroxyacetophenone
40815-74-5

4-allyloxy-2-hydroxyacetophenone

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; for 0.5h;79%
acetyl chloride
75-36-5

acetyl chloride

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With zinc at 64 - 66℃; for 0.0208333h; Friedel-Crafts acylation; microwave irradiation;77%
recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride at 20℃; for 12h;73%
With sulfuric acid; acetic acid In di-isopropyl ether; water72%
With sulfuric acid; acetic anhydride; acetic acid In water68%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With 1H-imidazole; acyltransferase from bacterium Pseudomonas sp.YGJ3 In aq. phosphate buffer at 35℃; for 24h; pH=8.3; Friedel-Crafts Acylation; Enzymatic reaction; regioselective reaction;68%
With 1H-imidazole; acyltransferase from pseudomonas protegens In aq. buffer at 35℃; for 18h; pH=8.3; Catalytic behavior; Reagent/catalyst; Concentration; pH-value; Friedel-Crafts Acylation;98 %Chromat.
With 1H-imidazole; acyltransferase from Pseudomonas protegens W211A mutant In aq. phosphate buffer; acetonitrile at 35℃; for 1.5h; pH=7.5; Catalytic behavior; Reagent/catalyst; Friedel-Crafts Acylation; Enzymatic reaction;66 %Chromat.
2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

recorcinol
108-46-3

recorcinol

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

Conditions
ConditionsYield
With cell-free E. coli extract containing the recombinant acyltransferase from Pseudomonas protegens In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 0.5h; pH=7.5; Catalytic behavior; Solvent; pH-value; Temperature; Enzymatic reaction;A 65%
B n/a
N-acetyl-(4-methylbenzene)sulfonamide
1888-33-1

N-acetyl-(4-methylbenzene)sulfonamide

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With zinc(II) chloride at 110 - 120℃;60%
Phenyl acetate
122-79-2

Phenyl acetate

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;60%
With 1H-imidazole; acyltransferase from pseudomonas protegens In aq. buffer at 35℃; for 18h; pH=8.3; Friedel-Crafts Acylation;> 99 %Chromat.
2,4-diacetoxy acetophenone
72712-19-7

2,4-diacetoxy acetophenone

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

2'-acetoxy-4'-hydroxyacetophenone
52751-42-5

2'-acetoxy-4'-hydroxyacetophenone

Conditions
ConditionsYield
With Candida cylindracea lipase In di-isopropyl ether; butan-1-ol at 28 - 30℃; for 11h;A 40%
B 50%
N-Acetylimidazole
2466-76-4

N-Acetylimidazole

recorcinol
108-46-3

recorcinol

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With acyltransferase from bacterium Pseudomonas sp.YGJ3 In aq. phosphate buffer at 35℃; for 18h; pH=7.5; Friedel-Crafts Acylation; Enzymatic reaction; regioselective reaction;41%
2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

1-(2-hydroxy-4-methoxyphenyl)ethanone
552-41-0

1-(2-hydroxy-4-methoxyphenyl)ethanone

C

1-(4-hydroxy-2-methoxy-phenyl)ethanone
493-33-4

1-(4-hydroxy-2-methoxy-phenyl)ethanone

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.5h; Heating;A 22%
B 16.3%
C 38%
isoliquirtigenin
961-29-5, 13745-20-5

isoliquirtigenin

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

5-hydroxy-2-(4-hydroxphenyl)chroman-4-one
64687-96-3

5-hydroxy-2-(4-hydroxphenyl)chroman-4-one

C

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

D

chalaurenol
85359-61-1

chalaurenol

Conditions
ConditionsYield
With Tris-HCl buffer; peroxidase from Amorpha fruticosa In 2-methoxy-ethanol at 30℃; for 3h;A n/a
B n/a
C n/a
D 25%
With Tris-HCl buffer; peroxidase from Amorpha fruticosa In 2-methoxy-ethanol at 30℃; for 3h; Mechanism;A n/a
B n/a
C n/a
D 25%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

recorcinol
108-46-3

recorcinol

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

Conditions
ConditionsYield
With cell-free E. coli extract containing the recombinant acyltransferase from Pseudomonas protegens In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 0.5h; pH=7.5; Enzymatic reaction;A 13%
B n/a
7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With potassium carbonate
Resorcinol diacetate
108-58-7

Resorcinol diacetate

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With aluminium trichloride at 185℃;
With zinc(II) chloride
acetic acid 3-methoxyphenyl ester
5451-83-2

acetic acid 3-methoxyphenyl ester

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

Conditions
ConditionsYield
With aluminium trichloride at 185℃;
2-(2,4-dihydroxy-phenyl)-4-methyl-chromen-7-one

2-(2,4-dihydroxy-phenyl)-4-methyl-chromen-7-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

acetic acid
64-19-7

acetic acid

C

recorcinol
108-46-3

recorcinol

2-(2,4-diethoxy-phenyl)-4-methyl-chromen-7-one

2-(2,4-diethoxy-phenyl)-4-methyl-chromen-7-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

acetic acid
64-19-7

acetic acid

C

2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

D

recorcinol
108-46-3

recorcinol

4,7-dihydroxy-3-[3,7,11-trimethyl-2(E),6(E),10-dodecatrienyl]coumarin
643-57-2

4,7-dihydroxy-3-[3,7,11-trimethyl-2(E),6(E),10-dodecatrienyl]coumarin

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

4,7-dihydroxy-3-methyl-2H-chromen-2-one
23687-21-0

4,7-dihydroxy-3-methyl-2H-chromen-2-one

Conditions
ConditionsYield
at 230℃; under 0.3 Torr;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone
111841-07-7

2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 1.5h; Ambient temperature;100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;98.3%
With pyridinium p-toluenesulfonate In dichloromethane for 12h; Ambient temperature;90%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

benzyl bromide
100-39-0

benzyl bromide

2,4-bis(benzyloxy)acetophenone
22877-01-6

2,4-bis(benzyloxy)acetophenone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 48h; Heating / reflux;100%
Stage #1: 2',4'-dihydroxy-4-acetophenone With potassium carbonate In acetonitrile at 85℃; for 0.0833333h; Inert atmosphere;
Stage #2: benzyl bromide at 85℃; for 12h; Inert atmosphere;
99%
With potassium carbonate In acetonitrile for 18h; Heating;97%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

methyl chloroformate
79-22-1

methyl chloroformate

2,4-bismethoxycarbonyloxyacetophenone

2,4-bismethoxycarbonyloxyacetophenone

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;100%
With triethylamine In tetrahydrofuran for 3h; Ambient temperature;94%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;105 g
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

benzyl bromide
100-39-0

benzyl bromide

1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone
29682-12-0

1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone

Conditions
ConditionsYield
Stage #1: 2',4'-dihydroxy-4-acetophenone With potassium carbonate In acetonitrile for 1h; Reflux;
Stage #2: benzyl bromide In acetonitrile Reflux;
99%
Stage #1: 2',4'-dihydroxy-4-acetophenone With potassium carbonate; potassium iodide In acetone at 50℃; for 0.5h;
Stage #2: benzyl bromide In acetone for 5h; Reflux;
97%
With potassium carbonate In acetone for 24h; Reflux;93%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2-hydroxy-4-(methoxymethoxy)acetophenone
65490-08-6

2-hydroxy-4-(methoxymethoxy)acetophenone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 4.5h;99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;96.8%
With potassium carbonate In acetone for 0.5h;95.6%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1-(2,4-dihydroxyphenyl)ethylamine
1228569-46-7

1-(2,4-dihydroxyphenyl)ethylamine

Conditions
ConditionsYield
With formate dehydrogenase; Arthrobacter citreus S9 ω-transaminase; ATA-113 ω-transaminase; sodium formate; isopropylamine; NADH; yeast alcohol dehydrogenase pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;99%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(1-(2,4-bis((tert-butyldimethylsilyl)oxy)phenyl)ethanone)

(1-(2,4-bis((tert-butyldimethylsilyl)oxy)phenyl)ethanone)

Conditions
ConditionsYield
With 1H-imidazole; dmap In dichloromethane at 0℃; Inert atmosphere;99%
With 1H-imidazole In N,N-dimethyl-formamide at 40℃; for 5.5h;78%
With 1H-imidazole In N,N-dimethyl-formamide at 40℃; for 5.5h;
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

bromethyl methyl ether
13057-17-5

bromethyl methyl ether

2-hydroxy-4-(methoxymethoxy)acetophenone
65490-08-6

2-hydroxy-4-(methoxymethoxy)acetophenone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;99%
With potassium carbonate In acetone at 50℃;64%
With potassium carbonate In acetone Reflux;59%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

benzoyl chloride
98-88-4

benzoyl chloride

2,4-dibenzoyloxyacetophenone
66832-97-1

2,4-dibenzoyloxyacetophenone

Conditions
ConditionsYield
With pyridine In diethyl ether at 0℃; for 1h;98.5%
With pyridine at 20℃; for 2h; Acylation;98%
With pyridine for 1h;83%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2',4'-bis(methoxymethoxy)acetophenone
6515-05-5

2',4'-bis(methoxymethoxy)acetophenone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate98.3%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 6.5h;98%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 5h; Ambient temperature;90%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1-(2,4-dihydroxy-3-iodophenyl)ethanone
71243-12-4

1-(2,4-dihydroxy-3-iodophenyl)ethanone

Conditions
ConditionsYield
With potassium iodate; iodine In ethanol; water at 20℃; Inert atmosphere;98%
With potassium iodate; iodine In ethanol; water at 20℃; Inert atmosphere; regiospecific reaction;98%
With potassium iodate; iodine In ethanol; water at 20℃; Inert atmosphere; regioselective reaction;98%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1-(2,4-dihydroxy-phenyl)-ethanone oxime
6134-79-8

1-(2,4-dihydroxy-phenyl)-ethanone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In water at 100℃; for 6h;98%
With hydroxylamine hydrochloride; sodium acetate In water for 6h; Reflux;98%
With hydroxylamine hydrochloride; sodium acetate In water at 70℃; for 6h;79%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1-(2,4-dihydroxy-5-nitrophenyl)ethanone
3328-77-6

1-(2,4-dihydroxy-5-nitrophenyl)ethanone

Conditions
ConditionsYield
With zirconyl nitrate In acetone at 50℃; for 5h;98%
With yttrium(lll) nitrate hexahydrate In acetic acid at 20℃; for 3h;94%
With nitric acid; acetic acid at 20℃; for 7h; regioselective reaction;53.7%
2-(4-bromophenyl)acetyl chloride
37859-24-8

2-(4-bromophenyl)acetyl chloride

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

3-(p-bromophenyl)-7-(p-bromophenylacetoxy)-4-methylcoumarin
112030-39-4

3-(p-bromophenyl)-7-(p-bromophenylacetoxy)-4-methylcoumarin

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In benzene for 4h; Ambient temperature;98%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

2,4-bis<<2-(trimethylsilyl)ethoxy>methoxy>acetophenone
107913-74-6

2,4-bis<<2-(trimethylsilyl)ethoxy>methoxy>acetophenone

Conditions
ConditionsYield
With dmap; triethylamine In benzene at 110℃; for 3h;98%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

allyl bromide
106-95-6

allyl bromide

1-(2,4-bis(allyloxy)phenyl)ethanone
2079-52-9

1-(2,4-bis(allyloxy)phenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate Inert atmosphere;98%
With potassium carbonate In N,N-dimethyl-formamide98%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 5h; Inert atmosphere;98%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 5h;98%
With potassium carbonate In acetone for 12h; Heating;59.2%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

phenylacetyl chloride
103-80-0

phenylacetyl chloride

4-methyl-3-phenyl-7-phenylacetoxy coumarin
112030-33-8

4-methyl-3-phenyl-7-phenylacetoxy coumarin

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In benzene for 4h; Ambient temperature;98%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

acetone
67-64-1

acetone

7-hydroxy-2,2-dimethyl-chroman-4-one
17771-33-4

7-hydroxy-2,2-dimethyl-chroman-4-one

Conditions
ConditionsYield
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation;98%
With Amberlite IRA 400 basic resin for 0.0833333h; Microwave irradiation; Neat (no solvent);89%
With pyrrolidine In toluene for 14h; Heating;86.7%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

hydroxylamine hydrochloride
5470-11-1

hydroxylamine hydrochloride

(1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime
111364-29-5

(1Z)-1-(2,4-dihydroxyphenyl)ethanone oxime

Conditions
ConditionsYield
In pyridine at 20℃;98%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

butanone
78-93-3

butanone

2-ethyl-7-hydroxy-2-methyl-chroman-4-one
59258-08-1

2-ethyl-7-hydroxy-2-methyl-chroman-4-one

Conditions
ConditionsYield
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation;98%
With Amberlite IRA 400 basic resin for 0.133333h; Microwave irradiation; Neat (no solvent);85%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

propargyl bromide
106-96-7

propargyl bromide

1-(2,4-bis(prop-2-yn-1-yloxy)phenyl)ethan-1-one
22287-70-3

1-(2,4-bis(prop-2-yn-1-yloxy)phenyl)ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;98%
With potassium carbonate In acetone for 48h; Reflux;
With potassium carbonate In toluene for 12h; Reflux;
Stage #1: 2',4'-dihydroxy-4-acetophenone With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 17h; Inert atmosphere;
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

(E)-4-(1-hydrazonoethyl)benzene-1,3-diol
19363-41-8

(E)-4-(1-hydrazonoethyl)benzene-1,3-diol

Conditions
ConditionsYield
With hydrazine hydrate In N,N-dimethyl-formamide at 20℃; for 4h;97%
With hydrazine hydrate; acetic acid In methanol at 20℃;82%
With ethanol; hydrazine
With hydrazine hydrate In water for 0.0333333h; Microwave irradiation;
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

acetic anhydride
108-24-7

acetic anhydride

2,4-diacetoxy acetophenone
72712-19-7

2,4-diacetoxy acetophenone

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 0.5h;97%
With pyridine; aluminum oxide at 120 - 122℃; for 1h; microwave irradiation;54%
With sodium acetate bei 0.5 Minuten langem Kochen;
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

prenyl bromide
870-63-3

prenyl bromide

1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]ethanone
24672-83-1

1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone at 80℃; Williamson Ether Synthesis;97%
With potassium carbonate In acetone for 8h; Reflux;89%
With potassium carbonate In acetone at 80℃; for 6h;82%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

ethyl iodide
75-03-6

ethyl iodide

1-(4-ethoxy-2-hydroxyphenyl)ethanone
37470-42-1

1-(4-ethoxy-2-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone at 80℃; for 6h;97%
With potassium carbonate In N,N-dimethyl-formamide for 4h;63%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

isobutyryl chloride
79-30-1

isobutyryl chloride

2',4'-di-(2-methylpropanoyloxy)-acetophenone
957272-64-9

2',4'-di-(2-methylpropanoyloxy)-acetophenone

Conditions
ConditionsYield
With pyridine at 20℃;97%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

cyclohexanone
108-94-1

cyclohexanone

7-hydroxy-spiro<2H-1-benzopyran-2,1'-cyclohexane>-4(3H)-one
62756-43-8

7-hydroxy-spiro<2H-1-benzopyran-2,1'-cyclohexane>-4(3H)-one

Conditions
ConditionsYield
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation;97%
With Amberlite IRA 400 basic resin for 0.1h; Microwave irradiation; Neat (no solvent);90%
With pyrrolidine In acetonitrile at 45℃; for 8h;84%

89-84-9Relevant articles and documents

Anticancer activity of some newly synthesized pyrano[2,3-d][1,2,3]triazine derivatives using 1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone as synthon

Ouf, Nabil H.,Amr, Abd El-Galil E.,Sakran, Mohamed I.

, p. 1514 - 1526 (2015)

A series of the newly substituted pyrano[1,2,3]triazine derivatives 3-14 were synthesized using compounds 1 and 2 as starting materials. Compound 2 was methylated using methyl iodide to compound 3, which was treated with aromatic aldehydes to give acryloyl derivatives 4a-c. Compounds 4a,b were reacted with ethyl cyano-acetate to give pyran-3-carboxylates 5a,b which were reacted with ethyl glycinate hydrochloride to give 6a,b. Treatment of 6a,b with hydrazine hydrate gives acid hydrazides 7a,b, which were reacted with 5,5-dimethyl-1,3-cyclohexanedione to give acetohydrazides 8a,b. Cyclization of 8b with 2-(4-nitrobenzylidene)malononitrile afforded hexahydroquinoline 9. However, the acridindione 10 was synthesized by heating of 8b with 2-(4-nitrobenzylidene)malononitrile in acetic acid containing few drops of triethylamine. Treatment of 7a,b with phenyl isothiocyanate or 2,5-hexanedione or phthalic anhydride gave compounds 11a,b, 13a,b and 14a,b, respectively. In the present work, all the selected pyrano[1,2,3]trizine derivatives were soluble in DMSO at concentrations high enough to allow cell experiments, and the in vitro biological activity of these compounds was evaluated by their growth inhibitory potency in liver HEPG2 cancer cell lines. The cytotoxic potency of compounds 3-14 was studied in comparison to the known anticancer drugs 5-fluorouracil and doxorubicin.

Loewe

, p. 931,934 (1977)

EGFR/VEGFR-2 dual inhibitor and apoptotic inducer: Design, synthesis, anticancer activity and docking study of new 2-thioxoimidazolidin-4one derivatives

Mourad, Ahmed A.E.,Farouk,El-Sayed, El-Sherbiny H.,Mahdy, Ahmed R.E.

, (2021/04/23)

Aims: EGFR and VEGFR-2 have emerged as promising targets for cancer management as they play a crucial role in tumor growth, angiogenesis and metastasis. A novel series of 2-thioxoimidazolidin-4-one derivatives were synthesized and evaluated as apoptotic inducers and EGFR/VEGFR-2 dual inhibitors. Main methods: The cytotoxic activities of all synthesized compounds were tested against MCF-7, HepG2 and A549 cell lines. The molecular mechanism of the most promising cytotoxic compounds was investigated via a series of assays including in vitro EGFR and VEGFR-2 inhibitory activity in MCF-7 cell line. Additionally, levels of p53, Bax, Bcl-2, caspase 7, 9 as well as cell cycle analysis were assessed in MCF-7 cell line to gain better understanding of their apoptotic activity. Molecular docking study was carried out to predict binding pattern of these compounds with EGFR and VEGFR-2 active sites. Finally, in silico ADME and drug-likeness profiling were calculated. Key findings: Compounds 6 and 8a exhibited superior cytotoxic activity compared to sorafenib and erlotinib, against the three tested cell lines. In the same context, 6 and 8a showed better EGFR and VEGFR-2 inhibitory activity compared to the reference compounds. The later effect was further supported by the docking study. Furthermore, these compounds displayed potent apoptotic activity as evident by cell accumulation at pre-G1 phase and cell cycle arrest at G2/M phase together with increased p53, caspae-7 and caspase-9 levels and Bax/Bcl-2 ratio. Finally, synthesized compounds have acceptable drug likeness. Significance: Compounds 6 and 8a act as potent dual EGFR/VEGFR-2 inhibitors with evident apoptotic activity.

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey

supporting information, (2021/06/03)

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

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