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490-78-8

Basic Information
CAS No.: 490-78-8
Name: 2',5'-Dihydroxyacetophenone
Article Data: 89
Molecular Structure:
Molecular Structure of 490-78-8 (2',5'-Dihydroxyacetophenone)
Formula: C8H8O3
Molecular Weight: 152.15
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;
EINECS: 207-716-4
Density: 1.291 g/cm3
Melting Point: 204-206 °C(lit.)
Boiling Point: 329.2 °C at 760 mmHg
Flash Point: 167.1 °C
Solubility: insoluble in water
Appearance: yellow to yellow-green crystals
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 57.53000
LogP: 1.30040
Synthetic route
64-19-7

acetic acid

123-31-9

hydroquinone

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%
108-24-7

acetic anhydride

123-31-9

hydroquinone

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%
127-17-3

2-oxo-propionic acid

106-51-4

p-benzoquinone

490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With ammonium persulfate; silver nitrate In water; acetonitrile at 70℃; for 2h;92%
1205-91-0

benzene-1,4-diyl diacetate

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%
40815-75-6

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

490-78-8

2,5-Dihydroxyacetophenone

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

Dipropyl ether

1205-91-0

benzene-1,4-diyl diacetate

A

490-78-8

2,5-Dihydroxyacetophenone

B

288074-68-0

2-hydroxy-5-propoxyacetophenone

Conditions
ConditionsYield
With boron trifluoride for 1h; Fries rearrangement; Heating;A 89%
B 9%
705-15-7

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

490-78-8

2,5-Dihydroxyacetophenone

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

(+)-euryfuran

1125-55-9

2-Acetyl-1,4-benzoquinone

A

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

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

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%
1125-55-9

2-Acetyl-1,4-benzoquinone

55562-82-8

trimethyl(2-methyl-2-propenyl)stannane

A

490-78-8

2,5-Dihydroxyacetophenone

B

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

Conditions
ConditionsYield
In benzeneA 6%
B 77%
1201-38-3

2',5'-dimethoxyacetophenone

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
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Chemistry

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

Uses

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

Production

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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

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.