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2',5'-Dihydroxyacetophenone

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Name

2',5'-Dihydroxyacetophenone

EINECS 207-716-4
CAS No. 490-78-8 Density 1.291 g/cm3
PSA 57.53000 LogP 1.30040
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 N/A 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;

Article Data 89

2',5'-Dihydroxyacetophenone 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

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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