2',6'-Dihydroxyacetophenone supplier

Name
2',6'-Dihydroxyacetophenone
EINECS 211-833-6
CAS No. 699-83-2
Article Data27
CAS DataBase
Density 1.291 g/cm³
Solubility sparingly soluble in water
Melting Point 156-158 °C(lit.)
Formula C₈H₈O₃
Boiling Point 262.8 °C at 760 mmHg
Molecular Weight 152.15
Flash Point 127 °C
Transport Information
Appearance yellowish-beige powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Acetophenone,2,6-dihydroxy- (3CI);Acetophenone, 2',6'-dihydroxy- (7CI,8CI);1,3-Benzenediol, 2-acetyl-;1-(2,6-Dihydroxyphenyl)ethanone;2-Acetylbenzene-1,3-diol;2-Acetylresorcinol;Ethanone,1-(2,6-dihydroxyphenyl)-;NSC615;
PSA 57.53000
LogP 1.30040

Synthetic route

: 144152-28-3
2,6-diacetoxyacetophenone

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With water; sodium acetate In ethanol for 5h; Reflux;	92%

: 108-58-7
Resorcinol diacetate

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With hydrogen fluoride supported on silica gel In neat (no solvent) at 55℃; for 4h; Green chemistry;	60%
With Fluoro Flash In neat (no solvent) at 80℃; for 4h; Catalytic behavior; Fries Phenol Ester Rearrangement; Green chemistry;

: 30992-74-6
4,5-dihydroxy-2H-benzopyran-2-one

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With potassium hydroxide

: 2555-29-5
8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With sodium hydroxide

: 2040-04-2
2,6-dimethoxyacetophenone

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With aluminium trichloride; chlorobenzene auf Siedetemperatur;
With aluminium trichloride; toluene at 120℃;

: 62970-17-6
3-acetyl-2,4-dihydroxy-benzoic acid methyl ester

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With sodium hydroxide

: 52956-20-4
2-acetyl-2-chloro-1,3-cyclohexanedione

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide
(i) HCl, DMF, (ii) aq. HCl; Multistep reaction;
With hydrogenchloride In d7-N,N-dimethylformamide at 120 - 130℃; for 0.333333h; Yield given;

: 108-24-7
acetic anhydride

: 141-97-9
ethyl acetoacetate

: 108-46-3
recorcinol

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: 37514-00-4
2-acetyl-1,3-cyclohexanedione enol

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With mercury(II) diacetate; sodium acetate In acetic acid

: 7446-70-0
aluminium trichloride

: 2040-04-2
2,6-dimethoxyacetophenone

: 108-90-7
chlorobenzene

: 699-83-2
2,6-dihydroxylacetophenone

...Expand

: 7446-70-0
aluminium trichloride

: 2040-04-2
2,6-dimethoxyacetophenone

: 108-88-3
toluene

: 699-83-2
2,6-dihydroxylacetophenone

...Expand

: 16932-49-3
2,6-dimethoxybenzonitrile

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene; diethyl ether / Erhitzen des vom Aether befreiten Reaktionsgemisches auf Siedetemperatur,anshcliessendes Behandeln mit Eis und wss.HCl und Erwaermen der erhaltenen wss.Loesung 2: AlCl3; chlorobenzene / auf Siedetemperatur View Scheme
Multi-step reaction with 2 steps 1: toluene; diethyl ether / Erhitzen des vom Aether befreiten Reaktionsgemisches auf Siedetemperatur,anshcliessendes Behandeln mit Eis und wss.HCl und Erwaermen der erhaltenen wss.Loesung 2: AlCl3; toluene / 120 °C View Scheme

: 1795-39-7
NSC 251156

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium chloride / 215 °C 2: aqueous KOH View Scheme

: 108-46-3
recorcinol

phenoldiazonium chloride-(4): phenoldiazonium chloride-(4)

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 250 °C 2: aluminium chloride / 215 °C 3: aqueous KOH View Scheme

: 108-46-3
recorcinol

: 699-83-2
2,6-dihydroxylacetophenone

: 75-36-5
acetyl chloride

: 95-50-1
1,2-dichloro-benzene

: 108-46-3
recorcinol

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With hydrogenchloride; aluminium trichloride

...Expand

: 4056-73-9
2-acetyl-1,3-cyclohexanedione

: 7783-06-4
hydrogen sulfide

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
In toluene	0.91 g (59 mole %)

: tetraethylene glycol dimethyl ether

: 4056-73-9
2-acetyl-1,3-cyclohexanedione

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
In isopropyl alcohol

: 75-36-5
acetyl chloride

: 108-46-3
recorcinol

: 699-83-2
2,6-dihydroxylacetophenone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;

: 699-83-2
2,6-dihydroxylacetophenone

: 109-70-6
1,3-chlorobromopropane

: 105277-74-5
2-(3-chlorophenoxy)-6-hydroxyacetophenone

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	46%
With potassium carbonate In acetone

: 699-83-2
2,6-dihydroxylacetophenone

: 149071-05-6
3-methyl-4-hydroxyindazole

Conditions

Conditions	Yield
With hydrazine hydrate In ethylene glycol at 20 - 160℃; for 2.5h;	100%
With hydrazine hydrate In ethylene glycol at 160℃; for 2h; Cyclization;	68%
With hydrazine In ethylene glycol at 20 - 160℃; for 2.33333h;	68%

: 699-83-2
2,6-dihydroxylacetophenone

: 100-44-7
benzyl chloride

: 3886-19-9
1-[2',6'-bis(phenylmethoxy)phenyl]ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65 - 100℃; for 18h;	99%

: 699-83-2
2,6-dihydroxylacetophenone

: 609-65-4
o-chlorobenzoyl chloride

: 920006-37-7
2',6'-bis(2-chlorobenzoyloxy)acetophenone

Conditions

Conditions	Yield
With pyridine; dmap at 20℃; for 2h;	99%

: 75-77-4
chloro-trimethyl-silane

: 699-83-2
2,6-dihydroxylacetophenone

: 1146968-51-5
C14H24O3Si2

Conditions

Conditions	Yield
Stage #1: 2,6-dihydroxylacetophenone With lithium diisopropyl amide In tetrahydrofuran Stage #2: chloro-trimethyl-silane In tetrahydrofuran	99%

: 699-83-2
2,6-dihydroxylacetophenone

: 74-88-4
methyl iodide

: 703-23-1
2'-hydroxy-6'-methoxyacetophenone

Conditions

Conditions	Yield
With potassium carbonate In acetone for 4h; Heating;	98%
With potassium carbonate In acetone for 8h; Reflux;	97%
With potassium carbonate In acetone at 55℃; for 8h;	95%

: 699-83-2
2,6-dihydroxylacetophenone

: 122-04-3
4-nitro-benzoyl chloride

: 26505-98-6
2',6'-bis(4-nitrobenzoyloxy)acetophenone

Conditions

Conditions	Yield
With pyridine at 20℃; for 12h;	98%

: 699-83-2
2,6-dihydroxylacetophenone

: 107-30-2
chloromethyl methyl ether

: 78646-28-3
2′-hydroxy-6′-methoxymethoxyacetophenone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 4.5h;	97.8%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h;	95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	92.8%

: 699-83-2
2,6-dihydroxylacetophenone

: 77-78-1
dimethyl sulfate

: 703-23-1
2'-hydroxy-6'-methoxyacetophenone

Conditions

Conditions	Yield
Stage #1: 2,6-dihydroxylacetophenone With potassium carbonate In acetone for 0.166667h; Stage #2: dimethyl sulfate In acetone for 6h; Reflux;	96%
With potassium carbonate In acetone for 2h; Inert atmosphere; Reflux;	96%
With potassium carbonate In acetone for 0.333333h; Reflux;	95%

: 699-83-2
2,6-dihydroxylacetophenone

: 18162-48-6
tert-butyldimethylsilyl chloride

: 466635-70-1
2,6-bis(tert-butyldimethylsilyloxy)acetophenone

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 20h;	96%

: 699-83-2
2,6-dihydroxylacetophenone

: 928-68-7
6-methylheptan-2-one

: 5-hydroxy-2-methyl-2-(4-methylpentyl)chroman-4-one

Conditions

Conditions	Yield
Stage #1: 6-methylheptan-2-one With pyrrolidine; butyric acid In dimethyl sulfoxide for 0.25h; Kabe Chromanone Synthesis; Stage #2: 2,6-dihydroxylacetophenone In dimethyl sulfoxide at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Kabe Chromanone Synthesis;	95%
With pyrrolidine In toluene Dean-Stark; Reflux;

: 699-83-2
2,6-dihydroxylacetophenone

: 100-07-2
4-methoxy-benzoyl chloride

: 58124-15-5
2',6'-bis(4-methoxybenzoyloxy)acetophenone

Conditions

Conditions	Yield
With pyridine at 20℃; for 12h;	94%
With pyridine
With pyridine for 2h;

: 699-83-2
2,6-dihydroxylacetophenone

: 3282-30-2
pivaloyl chloride

: 2-acetyl-1,3-phenylene bis(2,2-dimethylpropanoate)

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 23℃; for 3h; Inert atmosphere;	94%

: 699-83-2
2,6-dihydroxylacetophenone

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 23141-00-6
2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)

Conditions

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In chloroform at 20℃; for 24h; glycosylation;	93%
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In chloroform; water at 20℃; for 27h;	9%

: 699-83-2
2,6-dihydroxylacetophenone

: 79-22-1
methyl chloroformate

: Carbonic acid 2-acetyl-3-methoxycarbonyloxy-phenyl ester methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran 0 deg C to room temp., 0.5 to 1 h;	92%

: 699-83-2
2,6-dihydroxylacetophenone

: 122-01-0
4-chloro-benzoyl chloride

: 502916-43-0
2',6'-bis(4-chlorobenzoyloxy)acetophenone

Conditions

Conditions	Yield
With pyridine at 20℃; for 12h;	92%
With pyridine for 2h;

: 699-83-2
2,6-dihydroxylacetophenone

: 1866-39-3
trans-p-methylcinnamic acid

: 2',6'-di(4-methylcinnamoyloxy)acetophenone

Conditions

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	92%

: 699-83-2
2,6-dihydroxylacetophenone

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1193107-75-3
1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 13h; Inert atmosphere;	92%

: 699-83-2
2,6-dihydroxylacetophenone

: 109-94-4
formic acid ethyl ester

: 3952-69-0
5-hydroxy-4H-1-benzopyran-4-one

Conditions

Conditions	Yield
Stage #1: 2,6-dihydroxylacetophenone; formic acid ethyl ester With sodium ethanolate at 0 - 20℃; for 18h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 0 - 20℃; for 24h;	92%

: 699-83-2
2,6-dihydroxylacetophenone

: 87953-93-3
3-chloro-2.6-dihydroxyacetophenone

Conditions

Conditions	Yield
With sulfuryl dichloride In acetic acid for 2h; Heating;	90.5%
With N-chloro-succinimide; acetic acid at 50℃; for 2h;	81.5%
With thionyl chloride In acetic acid
With thionyl chloride In acetic acid
With N-chloro-succinimide; acetic acid at 50℃; for 2h;

: 699-83-2
2,6-dihydroxylacetophenone

: 4074-50-4
2-ethylbenzene-1,3-diol

Conditions

Conditions	Yield
With hydrogenchloride; sodium cyanoborohydride In methanol	90%
With triethylsilane In trifluoroacetic acid at 20℃; for 3h; Inert atmosphere;	81%
With triethylsilane; trifluoroacetic acid for 3h;	78%

: 699-83-2
2,6-dihydroxylacetophenone

: 150942-98-6
t-butyl lithioacetate

: 2,5-Dihydroxy-2-methyl-chroman-4-one

Conditions

Conditions	Yield
In toluene at 100℃; for 2h;	90%

: 699-83-2
2,6-dihydroxylacetophenone

: 100-46-9
benzylamine

: 82488-60-6
2,6-Dihydroxyphenylethylidenebenzylamine

Conditions

Conditions	Yield
In toluene Heating; or ZnCl2, 1) 30 min, 160 deg C, 2) 5 min, 180 deg C;	90%
In toluene Heating;	90%

: 699-83-2
2,6-dihydroxylacetophenone

: 1201-99-6, 20595-45-3, 20595-46-4
trans-2,4-dichlorocinnamic acid

: 2',6'-di(2,4-dichlorocinnamoyloxy)acetophenone

Conditions

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	90%

: 699-83-2
2,6-dihydroxylacetophenone

: 105-36-2
ethyl bromoacetate

: 6769-65-9
ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 2h;	89%
With potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature;	80%
With potassium carbonate In acetone for 3h; Reflux;	61%
With potassium carbonate; acetone
With potassium carbonate In acetone at 60℃; for 15h;

: 699-83-2
2,6-dihydroxylacetophenone

: 100-39-0
benzyl bromide

: 3886-19-9
1-[2',6'-bis(phenylmethoxy)phenyl]ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2.5h;	89%
With potassium carbonate; sodium iodide In acetone for 18h; Heating;	46%
With sodium iodide; potassium carbonate In acetone
With potassium carbonate In dimethyl sulfoxide at 20℃;

: 699-83-2
2,6-dihydroxylacetophenone

: 100-44-7
benzyl chloride

: 4047-24-9
1-[2-(benzyloxy)-6-hydroxyphenyl]ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 70℃; Inert atmosphere;	89%
With potassium carbonate In N,N-dimethyl-formamide for 24h;	78%
With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;	68%
With potassium carbonate In N,N-dimethyl-formamide

: 699-83-2
2,6-dihydroxylacetophenone

: 704-96-1
trans-2-chlorocinnamic acid

: 2'-(2-chlorocinnamoyloxy)-6'-hydroxyacetophenone

Conditions

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	89%

: 699-83-2
2,6-dihydroxylacetophenone

: 143-15-7
1-dodecylbromide

: 1393845-50-5
1-(2-(dodecyloxy)-6-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile at 70 - 80℃;	88%

2',6'-Dihydroxyacetophenone Chemical Properties

Molecule structure of 2',6'-Dihydroxyacetophenone (CAS NO.699-83-2):

IUPAC Name: 1-(2,6-Dihydroxyphenyl)ethanone
Molecular Weight: 152.14732 g/mol
Molecular Formula: C₈H₈O₃
Density: 1.291 g/cm³
Melting Point: 156-158 °C(lit.)
Boiling Point: 262.8 °C at 760 mmHg
Flash Point: 127 °C
Index of Refraction: 1.595
Molar Refractivity: 40.04 cm³
Molar Volume: 117.8 cm³
Surface Tension: 56.1 dyne/cm
Enthalpy of Vaporization: 52.08 kJ/mol
Vapour Pressure: 0.00656 mmHg at 25 °C
Solubility Dioxane: 50 mg/mL, clear
Water Solubility: sparingly soluble
XLogP3-AA: 1.4
H-Bond Donor: 2
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Tautomer Count: 12
Exact Mass: 152.047344
MonoIsotopic Mass: 152.047344
Topological Polar Surface Area: 57.5
Heavy Atom Count: 11
Canonical SMILES: CC(=O)C1=C(C=CC=C1O)O
InChI: InChI=1S/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3
InChIKey: YPTJKHVBDCRKNF-UHFFFAOYSA-N
EINECS: 211-833-6
Product Categories: FINE Chemical & INTERMEDIATES; Cromoglyn Sodium; Acetophenone series

2',6'-Dihydroxyacetophenone Uses

2',6'-Dihydroxyacetophenone (CAS NO.699-83-2) is used in organic synthesis. It is also used as pharmaceutical intermediates.

2',6'-Dihydroxyacetophenone Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29145000

2',6'-Dihydroxyacetophenone Specification

2',6'-Dihydroxyacetophenone (CAS NO.699-83-2) is also named as 1,3-Benzenediol, 2-acetyl- ; 2,6-Dihydroxyacetophenone ; 2-Acetylresorcinol ; NSC 615 ; Resorcinol, 2-acetyl- ; gamma-Resacetophenone ; Acetophenone, 2',6'-dihydroxy- (8CI) ; Ethanone, 1-(2,6-dihydroxyphenyl)- (9CI) . 2',6'-Dihydroxyacetophenone (CAS NO.699-83-2) is yellowish-beige powder.

Product Name

2',6'-Dihydroxyacetophenone

Synthetic route

2',6'-Dihydroxyacetophenone Chemical Properties

2',6'-Dihydroxyacetophenone Uses

2',6'-Dihydroxyacetophenone Safety Profile

2',6'-Dihydroxyacetophenone Specification

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