Product Name

  • Name

    2',5'-Dihydroxyacetophenone

  • EINECS 207-716-4
  • CAS No. 490-78-8
  • Article Data89
  • CAS DataBase
  • Density 1.291 g/cm3
  • Solubility insoluble in water
  • Melting Point 204-206 °C(lit.)
  • Formula C8H8O3
  • Boiling Point 329.2 °C at 760 mmHg
  • Molecular Weight 152.15
  • Flash Point 167.1 °C
  • Transport Information
  • Appearance yellow to yellow-green crystals
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 490-78-8 (2',5'-Dihydroxyacetophenone)
  • Hazard Symbols IrritantXi
  • Synonyms 3,5-Dihydroxy acetophenone;2,5-dihydroxyacetophenone;Acetophenone,2',5'-dihydroxy- (7CI,8CI);1-(2,5-Dihydroxyphenyl)ethanone;1-Acetyl-2,5-dihydroxybenzene;2,5-Dihydroxy-1-acetylbenzene;2-Acetyl-1,4-benzenediol;2-Acetylhydroquinone;NSC 3759;Quinacetophenone;
  • PSA 57.53000
  • LogP 1.30040

Synthetic route

acetic acid
64-19-7

acetic acid

hydroquinone
123-31-9

hydroquinone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 0.0333333h; microwave irradiation;98%
With iron(III) chloride for 0.0166667h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction;98%
With aluminum oxide; methanesulfonic acid at 120℃; for 0.333333h;85%
acetic anhydride
108-24-7

acetic anhydride

hydroquinone
123-31-9

hydroquinone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
Stage #1: acetic anhydride; hydroquinone In 1,2-dichloro-ethane at 100℃; for 4h; Friedel-Crafts Acylation;
Stage #2: With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 120℃; for 3h;
92%
zinc(II) chloride at 145 - 150℃; for 0.25h;76%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

p-benzoquinone
106-51-4

p-benzoquinone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With ammonium persulfate; silver nitrate In water; acetonitrile at 70℃; for 2h;92%
benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
for 0.116667h; Rearrangement; microwave irradiation;90%
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h;
Stage #2: With hydrogenchloride; water for 0.5h; Reflux;
85%
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 180℃; for 3h; Fries rearrangement;
Stage #2: With hydrogenchloride In methanol Reflux;
76.6%
1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone
40815-75-6

1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating;89%
Dipropyl ether
111-43-3

Dipropyl ether

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

B

2-hydroxy-5-propoxyacetophenone
288074-68-0

2-hydroxy-5-propoxyacetophenone

Conditions
ConditionsYield
With boron trifluoride for 1h; Fries rearrangement; Heating;A 89%
B 9%
1-(2-hydroxy-5-methoxyphenyl)ethan-1-one
705-15-7

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate for 0.025h; microwave irradiation;85%
(+)-euryfuran
67919-45-3

(+)-euryfuran

2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

A

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

B

2-acetyl-3-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-1,4-benzoquinone

2-acetyl-3-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-1,4-benzoquinone

C

3,6-dihydroxy-2-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-acetophenone

3,6-dihydroxy-2-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-acetophenone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5h; Michael reaction;A n/a
B 80%
C 17%
In dichloromethane at 20℃; for 5h; Arylation;A n/a
B 51%
C 17%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

trimethyl(2-methyl-2-propenyl)stannane
55562-82-8

trimethyl(2-methyl-2-propenyl)stannane

A

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

B

2-acetyl-3-(2-methylallyl)-1,4-benzenediol

2-acetyl-3-(2-methylallyl)-1,4-benzenediol

Conditions
ConditionsYield
In benzeneA 6%
B 77%
2',5'-dimethoxyacetophenone
1201-38-3

2',5'-dimethoxyacetophenone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron dimethyl-trifluoro sulphide In dichloromethane at 20℃; for 1.5h;74%
With carbon disulfide; aluminum tri-bromide
With pyridine hydrochloride
4-methoxyphenyl acetate
1200-06-2

4-methoxyphenyl acetate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride at 140℃; for 2h; Fries rearrangement;71%
Fries rearrangement;
acetyl chloride
75-36-5

acetyl chloride

hydroquinone
123-31-9

hydroquinone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With zinc at 47 - 48℃; for 0.0166667h; Friedel-Crafts acylation; microwave irradiation;70%
With aluminium trichloride; nitrobenzene
hydroquinone
123-31-9

hydroquinone

Phenyl acetate
122-79-2

Phenyl acetate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;65%
5'-cinnamyloxy-2'-hydroxyacetophenone
79950-56-4

5'-cinnamyloxy-2'-hydroxyacetophenone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
at 220℃; for 20h;64%
2',5'-dimethoxyacetophenone
1201-38-3

2',5'-dimethoxyacetophenone

A

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one
705-15-7

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron dimethyl-trifluoro sulphide In dichloromethane at 0℃; for 0.166667h;A 64%
B 27%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

A

2-Acetyl-3-(3-acetyl-4-hydroxyphenoxy)-1,4-benzoquinone
68157-88-0

2-Acetyl-3-(3-acetyl-4-hydroxyphenoxy)-1,4-benzoquinone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With rose bengal In acetonitrile for 8h; Irradiation; Yields of byproduct given;A 60%
B n/a
benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

phenol
108-95-2

phenol

A

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 25%
B 60%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

A

5-hydroxy-2,3-dihydrobenzofuran-3-one
19278-82-1

5-hydroxy-2,3-dihydrobenzofuran-3-one

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
In benzene for 72h; Irradiation;A 50%
B 45%
In benzene for 72h; Mechanism; Irradiation;A 50%
B 45%
α-naphthol
90-15-3

α-naphthol

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

1-hydroxy-2-acetonaphthone
711-79-5

1-hydroxy-2-acetonaphthone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 20%
B 50%
benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

β-naphthol
135-19-3

β-naphthol

A

1-(2-hydroxy-1-naphthyl)ethan-1-one
574-19-6

1-(2-hydroxy-1-naphthyl)ethan-1-one

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 35%
B 45%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 35%
B 40%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

trimethyl(allyl)stannane
762-73-2

trimethyl(allyl)stannane

A

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
40815-79-0

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C

3a-acetyl-2-trimethylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

3a-acetyl-2-trimethylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

Conditions
ConditionsYield
In benzene for 5h;A 27%
B 36%
C 23%
In benzene dissolved acylquinone and allylstannane stood for 5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;A 27%
B 36%
C 23%
benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

1,4-diacetyl-2,5-dihydroxybenzene
20129-52-6

1,4-diacetyl-2,5-dihydroxybenzene

B

5'-Acetoxy-2'-hydroxyacetophenone
21222-04-8

5'-Acetoxy-2'-hydroxyacetophenone

C

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
In methanol for 12h; Irradiation;A 10%
B 15%
C 35%
acetophenone
98-86-2

acetophenone

A

3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

B

2,3,6-trihydroxyacetophenone
85918-30-5

2,3,6-trihydroxyacetophenone

C

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h; Mechanism; Product distribution;A 31%
B 4%
C 18%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h;A 31%
B 4%
C 18%
4a,8a-cis-4a-acetyl-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone
75925-74-5, 94842-18-9

4a,8a-cis-4a-acetyl-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With pyridine In xylene Heating;29%
(1R,4S)-4a-Acetyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione

(1R,4S)-4a-Acetyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
In pyridine; xylene at 120℃; for 3h;29%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

allyltributylstanane
24850-33-7

allyltributylstanane

A

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
40815-79-0

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C

3a-acetyl-2-tributylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

3a-acetyl-2-tributylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

Conditions
ConditionsYield
In benzene for 1.5h;A 29%
B 10%
C 10%
In benzene dissolved acylquinone and allylstannane stood for 1.5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;A 29%
B 10%
C 10%
2-acetylcyclohexanone
874-23-7

2-acetylcyclohexanone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide; dimethyl sulfoxide for 3h; Reflux;19%
2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

trimethyl(allyl)stannane
762-73-2

trimethyl(allyl)stannane

A

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
40815-79-0

2-acetyl-3-prop-2'-enyl-1,4-hydroquinone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
In acetonitrile dissolved acylquinone and allylstannane stood for 10 min under Ar; concentrated; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;A 18%
B 18%
benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

5'-Acetoxy-2'-hydroxyacetophenone
21222-04-8

5'-Acetoxy-2'-hydroxyacetophenone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride at 190 - 200℃;
Stage #1: benzene-1,4-diyl diacetate With aluminium trichloride; sodium chloride at 195℃; for 0.15h; Fries rearrangement;
Stage #2: With hydrogenchloride In water for 12h; Further stages. Title compound not separated from byproducts.;
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h;
Stage #2: With hydrogenchloride; water
ethyl (E)-4-methyl-3,5-hexadienoate
76200-27-6

ethyl (E)-4-methyl-3,5-hexadienoate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

(4aR,5R,8aS)-4a-Acetyl-5-(2-benzyloxy-ethyl)-6-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
72826-95-0, 80866-98-4

(4aR,5R,8aS)-4a-Acetyl-5-(2-benzyloxy-ethyl)-6-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

Conditions
ConditionsYield
With silver(l) oxide Ambient temperature; Absence of light;100%
C13H18O4
134637-25-5

C13H18O4

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C21H24O7
134637-35-7

C21H24O7

Conditions
ConditionsYield
With silver(l) oxide Ambient temperature;100%
C14H20O4
134637-27-7

C14H20O4

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C22H26O7
134637-38-0

C22H26O7

Conditions
ConditionsYield
With silver(l) oxide Ambient temperature;100%
C15H20O5
134685-78-2

C15H20O5

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C23H26O8
134637-30-2

C23H26O8

Conditions
ConditionsYield
With silver(l) oxide for 72h; Ambient temperature;100%
C16H22O5
134637-20-0

C16H22O5

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

C24H28O8
134637-32-4

C24H28O8

Conditions
ConditionsYield
With silver(l) oxide for 168h; Ambient temperature;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one
3557-22-0

1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;99%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;91%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 5h;87%
benzyl bromide
100-39-0

benzyl bromide

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

1-[2',5'-bis(phenylmethoxy)phenyl]ethanone
21766-81-4

1-[2',5'-bis(phenylmethoxy)phenyl]ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone for 18h; Etherification; Heating;99%
With potassium carbonate In acetone for 24h; Reflux;94%
Stage #1: 2,5-Dihydroxyacetophenone In 1,2-dimethoxyethane at 80℃; Inert atmosphere;
Stage #2: benzyl bromide In 1,2-dimethoxyethane; N,N-dimethyl-formamide for 12h;
93%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

6-hydroxy-4-methyl-2-oxo-2H-chromene-3-carboxylic acid

6-hydroxy-4-methyl-2-oxo-2H-chromene-3-carboxylic acid

Conditions
ConditionsYield
With kiwi juice In water at 20℃; for 0.0833333h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry;99%
With lithium perchlorate for 0.0194444h; Irradiation;83%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

(2-(1-(trimethylsilyloxy)vinyl)-1,4-phenylene)bis(oxy)bis(trimethylsilane)

(2-(1-(trimethylsilyloxy)vinyl)-1,4-phenylene)bis(oxy)bis(trimethylsilane)

Conditions
ConditionsYield
With triethylamine In dichloromethane at -30 - -10℃; for 0.666667h; Inert atmosphere; Sealed tube;99%
methyl chloroformate
79-22-1

methyl chloroformate

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Carbonic acid 3-acetyl-4-methoxycarbonyloxy-phenyl ester methyl ester

Carbonic acid 3-acetyl-4-methoxycarbonyloxy-phenyl ester methyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran 0 deg C to room temp., 0.5 to 1 h;98%
2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

isoprene
78-79-5

isoprene

(4aR,8aS)-4a-Acetyl-7-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

(4aR,8aS)-4a-Acetyl-7-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;97%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

5'-t-butyldimethylsilyloxy-2'-hydroxyacetophenone
843644-58-6

5'-t-butyldimethylsilyloxy-2'-hydroxyacetophenone

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;97%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

tert-butyl 4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate
849928-22-9

tert-butyl 4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate

Conditions
ConditionsYield
With pyrrolidine In methanol for 24h;97%
allyl bromide
106-95-6

allyl bromide

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone
40815-75-6

1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone

Conditions
ConditionsYield
With potassium carbonate In acetone for 18h; Heating;96%
With potassium carbonate; sodium iodide In acetone for 15h; Heating;86%
With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux;86%
2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

2-Acetyl-1,4-benzoquinone
1125-55-9

2-Acetyl-1,4-benzoquinone

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane for 0.25h; Ambient temperature;95%
With oxygen In chloroform; water at 20℃; under 760.051 Torr; for 6h;88%
With cerium(IV) ammonium nitrate; silica gel In dichloromethane for 0.25h;84%
benzyl bromide
100-39-0

benzyl bromide

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

5-benzyloxy-2-hydroxyacetophenone
30992-63-3

5-benzyloxy-2-hydroxyacetophenone

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate; potassium iodide In toluene at 115℃; for 14h;95%
With potassium carbonate In acetone for 48h; Reflux;92%
With sodium hydrogencarbonate In ethanol at 0 - 10℃; for 3.33333h;88.3%
ethylene glycol
107-21-1

ethylene glycol

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

acetylhydroquinone ethylene acetal

acetylhydroquinone ethylene acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 24h; Heating;95%
6,10,14-trimethyl-5,9,13-pentadecatriene-2-on
1117-52-8

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

6-Hydroxy-2-methyl-2-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-chroman-4-one
150035-61-3

6-Hydroxy-2-methyl-2-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-chroman-4-one

Conditions
ConditionsYield
With pyrrolidine; 3 A molecular sieve In ethanol Heating;95%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

2,2-dimethylpropanoic acid 2-acetyl-1,4-phenylene ester
309721-51-5

2,2-dimethylpropanoic acid 2-acetyl-1,4-phenylene ester

Conditions
ConditionsYield
With pyridine at 20℃;95%
With pyridine at 20℃; for 18h;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

6-hydroxy-4-oxo-4H-1-benzopyran
38445-24-8

6-hydroxy-4-oxo-4H-1-benzopyran

Conditions
ConditionsYield
With perchloric acid In water at 20 - 100℃; for 1.08333h;95%
With perchloric acid at 20℃; for 1.5h;78%
1-adamanthanol
768-95-6

1-adamanthanol

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

2',5'-dihydroxy-3'-(1-adamantyl)acetophenone

2',5'-dihydroxy-3'-(1-adamantyl)acetophenone

Conditions
ConditionsYield
With sulfuric acid In dichloromethane at 0℃; Inert atmosphere; Reflux;94.9%
2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

2-bromo-1-(2,5-dihydroxyphenyl)ethanone
25015-91-2

2-bromo-1-(2,5-dihydroxyphenyl)ethanone

Conditions
ConditionsYield
With aluminium trichloride; Montmorillonite K10; bromine In ethyl acetate at 20℃; for 2h;94%
With urea-hydrogen peroxide; acetic acid; sodium bromide; silica gel at 120 - 122℃; for 0.00611111h; microwave irradiation;71%
With copper(I) bromide In chloroform; ethyl acetate for 6h; Reflux;6%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

1-(2,5-bis(tert-butyldimethylsilyloxy)phenyl)ethanone
1431642-68-0

1-(2,5-bis(tert-butyldimethylsilyloxy)phenyl)ethanone

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;93.2%
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

tert-butyl 6-hydroxy-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate
911227-48-0

tert-butyl 6-hydroxy-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate

Conditions
ConditionsYield
With pyrrolidine In methanol at 60℃; for 48h;93%
With pyrrolidine In methanol for 18h; Reflux;87%
With pyrrolidine In methanol for 23h; Reflux;82%
6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

6-Hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-4-chromanon
69367-11-9

6-Hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-4-chromanon

Conditions
ConditionsYield
With pyrrolidine; 3 A molecular sieve In ethanol Heating;92%
2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

benzylamine
100-46-9

benzylamine

2,5-Dihydroxyphenylethylidenebenzylamine
82488-61-7

2,5-Dihydroxyphenylethylidenebenzylamine

Conditions
ConditionsYield
In toluene Heating; or ZnCl2, 1) 30 min, 160 deg C, 2) 5 min, 180 deg C;92%
In toluene Heating;90%
cyclohexanone
108-94-1

cyclohexanone

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

6-hydroxy-spiro-4-one
135110-68-8

6-hydroxy-spiro-4-one

Conditions
ConditionsYield
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation;92%
With pyrrolidine In ethanol Reflux;92%
With Amberlite IRA 400 basic resin for 0.133333h; Microwave irradiation; Neat (no solvent);86%
With pyrrolidine In isopropyl alcohol for 2h; Mechanism; Heating; other acetophenones;72%
With pyrrolidine In isopropyl alcohol for 2h; Heating;72%

2',5'-Dihydroxyacetophenone Chemical Properties

Molecular Formula:C8H8O3 
Molar mass:152.14732 g/mol
Structure :
                
Synonyms of 2',5'-Dihydroxyacetophenone(490-78-8):2-Acetylhydroquinone;Quinacetophenone;2,5-Dihydroxyacetophenone;Acetylquinol;Acetylhydroquinone;Acetophenone, 2',5'-dihydroxy-;Ethanone, 1-(2,5-dihydroxyphenyl)-
Density:1.291 g/cm3             
Flash Point:167.1 °C   
Boiling Point:329.2 °C at 760 mmHg       
Index of Refraction:1.595
Vapour Pressure:9.41E-05 mmHg at 25°C  
Melting point:204-206 °C
Water solubility:insoluble
Solubility:dioxane: 50 mg/mL, clear

2',5'-Dihydroxyacetophenone Uses

2',5'-Dihydroxyacetophenone(490-78-8) can be used in organic synthesis.

2',5'-Dihydroxyacetophenone Production

Derived by the reaction of Hydroquinone diacetate at the presence of aluminum chloride.

2',5'-Dihydroxyacetophenone Toxicity Data With Reference

1.   

ipr-mus LDLo:500 mg/kg

   CBCCT*    “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 5 (1953),140.
Carcinogenicity:2',5'-Dihydroxyacetophenone(490-78-8)- Not listed as a carcinogen by IARC, NTP,ACGIH,  or CA Prop 65.
Other: See actual entry in RTECS for complete information.

2',5'-Dihydroxyacetophenone Consensus Reports

Reported in EPA TSCA Inventory.

2',5'-Dihydroxyacetophenone Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:Xi
Risk Statements:
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

2',5'-Dihydroxyacetophenone Specification

Stability and Reactivity of 2',5'-Dihydroxyacetophenone(490-78-8):
Conditions to Avoid:strong oxidants,incompatible materials.
Chemical Stability:Stable under normal temperatures and pressures.
Incompatibilities with Other Materials:strong bases,strong oxidizing agents.
Hazardous Decomposition Products:Irritating and toxic fumes and gases,Carbon monoxide.
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