699-83-2

Basic information

• Product Name: 2',6'-Dihydroxyacetophenone
• Synonyms: Acetophenone, 2',6'-dihydroxy-;Acetyl-2,6-dihydroxybenzene;Ethanone, 1-(2,6-dihydroxyphenyl)-;gamma-Resacetophenone;Resorcinol, 2-acetyl-;DIHYDROXYACETOPHENONE(2,6-);2',6'-DIHYDROXYACETOPHENONE;2,6-DIHYDROXYACETOPHENONE
• CAS NO: 699-83-2
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 211-833-6
• Product Categories: FINE Chemical & INTERMEDIATES;Cromoglyn Sodium;Acetophenone series;Aromatics;Miscellaneous Reagents;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 699-83-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 156-158 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 127 °C
• Appearance: Yellow-beige/Powder
• Density: 1.2143 (rough estimate)
• Refractive Index: 1.4447 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: dioxane: 50 mg/mL, clear
• PKA: 9.65±0.10(Predicted)
• Water Solubility: sparingly soluble
• BRN: 1366061
• CAS DataBase Reference: 2',6'-Dihydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',6'-Dihydroxyacetophenone(699-83-2)
• EPA Substance Registry System: 2',6'-Dihydroxyacetophenone(699-83-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 699-83-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 699-83-2 differently. You can refer to the following data:
1. 2'',6''-Dihydroxyacetophenone (cas# 699-83-2) is a compound useful in organic synthesis.
2. Used with diammonium hydrogen citrate for MALDI-MS of PMP-labeled acidic and neutral glycans.

Preparation

Preparation by hydrolysis of 8-acetyl-4-methyl-umbelliferone (8-acetyl-7-hydroxy-4-methylcoumarin) with aqueous sodium hydroxide solution at reflux (56–73%).

Synthetic route

2,6-diacetoxyacetophenone (144152-28-3) → 2,6-dihydroxylacetophenone (699-83-2)

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

Resorcinol diacetate (108-58-7) → 2,6-dihydroxylacetophenone (699-83-2)

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;

4,5-dihydroxy-2H-benzopyran-2-one (30992-74-6) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
With potassium hydroxide

8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
With sodium hydroxide

2,6-dimethoxyacetophenone (2040-04-2) → 2,6-dihydroxylacetophenone (699-83-2)

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

3-acetyl-2,4-dihydroxy-benzoic acid methyl ester (62970-17-6) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
With sodium hydroxide

2-acetyl-2-chloro-1,3-cyclohexanedione (52956-20-4) → 2,6-dihydroxylacetophenone (699-83-2)

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;

acetic anhydride (108-24-7) + ethyl acetoacetate (141-97-9) + recorcinol (108-46-3) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
Multistep reaction;

2-acetyl-1,3-cyclohexanedione enol (37514-00-4) → 2,6-dihydroxylacetophenone (699-83-2)

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

aluminium trichloride (7446-70-0) + 2,6-dimethoxyacetophenone (2040-04-2) + chlorobenzene (108-90-7) → 2,6-dihydroxylacetophenone (699-83-2)

aluminium trichloride (7446-70-0) + 2,6-dimethoxyacetophenone (2040-04-2) + toluene (108-88-3) → 2,6-dihydroxylacetophenone (699-83-2)

2,6-dimethoxybenzonitrile (16932-49-3) → 2,6-dihydroxylacetophenone (699-83-2)

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

NSC 251156 (1795-39-7) → 2,6-dihydroxylacetophenone (699-83-2)

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

recorcinol (108-46-3) + phenoldiazonium chloride-(4) → 2,6-dihydroxylacetophenone (699-83-2)

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

recorcinol (108-46-3) → 2,6-dihydroxylacetophenone (699-83-2)

acetyl chloride (75-36-5) + 1,2-dichloro-benzene (95-50-1) + recorcinol (108-46-3) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
With hydrogenchloride; aluminium trichloride

2-acetyl-1,3-cyclohexanedione (4056-73-9) + hydrogen sulfide (7783-06-4) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
In toluene	0.91 g (59 mole %)

tetraethylene glycol dimethyl ether + 2-acetyl-1,3-cyclohexanedione (4056-73-9) → 2,6-dihydroxylacetophenone (699-83-2)

Conditions	Yield
In isopropyl alcohol

acetyl chloride (75-36-5) + recorcinol (108-46-3) → 2,6-dihydroxylacetophenone (699-83-2)

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

2,6-dihydroxylacetophenone (699-83-2) + 1,3-chlorobromopropane (109-70-6) → 2-(3-chlorophenoxy)-6-hydroxyacetophenone (105277-74-5)

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

2,6-dihydroxylacetophenone (699-83-2) → 3-methyl-4-hydroxyindazole (149071-05-6)

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%

2,6-dihydroxylacetophenone (699-83-2) + benzyl chloride (100-44-7) → 1-[2',6'-bis(phenylmethoxy)phenyl]ethanone (3886-19-9)

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

2,6-dihydroxylacetophenone (699-83-2) + o-chlorobenzoyl chloride (609-65-4) → 2',6'-bis(2-chlorobenzoyloxy)acetophenone (920006-37-7)

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

chloro-trimethyl-silane (75-77-4) + 2,6-dihydroxylacetophenone (699-83-2) → C14H24O3Si2 (1146968-51-5)

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

2,6-dihydroxylacetophenone (699-83-2) + methyl iodide (74-88-4) → 2'-hydroxy-6'-methoxyacetophenone (703-23-1)

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%

2,6-dihydroxylacetophenone (699-83-2) + 4-nitro-benzoyl chloride (122-04-3) → 2',6'-bis(4-nitrobenzoyloxy)acetophenone (26505-98-6)

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

2,6-dihydroxylacetophenone (699-83-2) + chloromethyl methyl ether (107-30-2) → 2′-hydroxy-6′-methoxymethoxyacetophenone (78646-28-3)

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%

2,6-dihydroxylacetophenone (699-83-2) + dimethyl sulfate (77-78-1) → 2'-hydroxy-6'-methoxyacetophenone (703-23-1)

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%

2,6-dihydroxylacetophenone (699-83-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2,6-bis(tert-butyldimethylsilyloxy)acetophenone (466635-70-1)

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

2,6-dihydroxylacetophenone (699-83-2) + 6-methylheptan-2-one (928-68-7) → 5-hydroxy-2-methyl-2-(4-methylpentyl)chroman-4-one

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;

2,6-dihydroxylacetophenone (699-83-2) + 4-methoxy-benzoyl chloride (100-07-2) → 2',6'-bis(4-methoxybenzoyloxy)acetophenone (58124-15-5)

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

2,6-dihydroxylacetophenone (699-83-2) + pivaloyl chloride (3282-30-2) → 2-acetyl-1,3-phenylene bis(2,2-dimethylpropanoate)

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

2,6-dihydroxylacetophenone (699-83-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) (23141-00-6)

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%

2,6-dihydroxylacetophenone (699-83-2) + methyl chloroformate (79-22-1) → Carbonic acid 2-acetyl-3-methoxycarbonyloxy-phenyl ester methyl ester

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

2,6-dihydroxylacetophenone (699-83-2) + 4-chloro-benzoyl chloride (122-01-0) → 2',6'-bis(4-chlorobenzoyloxy)acetophenone (502916-43-0)

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

2,6-dihydroxylacetophenone (699-83-2) + trans-p-methylcinnamic acid (1866-39-3) → 2',6'-di(4-methylcinnamoyloxy)acetophenone

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

2,6-dihydroxylacetophenone (699-83-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone (1193107-75-3)

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

2,6-dihydroxylacetophenone (699-83-2) + formic acid ethyl ester (109-94-4) → 5-hydroxy-4H-1-benzopyran-4-one (3952-69-0)

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%

2,6-dihydroxylacetophenone (699-83-2) → 3-chloro-2.6-dihydroxyacetophenone (87953-93-3)

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;

2,6-dihydroxylacetophenone (699-83-2) → 2-ethylbenzene-1,3-diol (4074-50-4)

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%

2,6-dihydroxylacetophenone (699-83-2) + t-butyl lithioacetate (150942-98-6) → 2,5-Dihydroxy-2-methyl-chroman-4-one

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

2,6-dihydroxylacetophenone (699-83-2) + benzylamine (100-46-9) → 2,6-Dihydroxyphenylethylidenebenzylamine (82488-60-6)

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

2,6-dihydroxylacetophenone (699-83-2) + trans-2,4-dichlorocinnamic acid (1201-99-6, 20595-45-3, 20595-46-4) → 2',6'-di(2,4-dichlorocinnamoyloxy)acetophenone

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

2,6-dihydroxylacetophenone (699-83-2) + ethyl bromoacetate (105-36-2) → ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate (6769-65-9)

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;

2,6-dihydroxylacetophenone (699-83-2) + benzyl bromide (100-39-0) → 1-[2',6'-bis(phenylmethoxy)phenyl]ethanone (3886-19-9)

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℃;

2,6-dihydroxylacetophenone (699-83-2) + benzyl chloride (100-44-7) → 1-[2-(benzyloxy)-6-hydroxyphenyl]ethanone (4047-24-9)

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

2,6-dihydroxylacetophenone (699-83-2) + trans-2-chlorocinnamic acid (704-96-1) → 2'-(2-chlorocinnamoyloxy)-6'-hydroxyacetophenone

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

2,6-dihydroxylacetophenone (699-83-2) + 1-dodecylbromide (143-15-7) → 1-(2-(dodecyloxy)-6-hydroxyphenyl)ethanone (1393845-50-5)

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

Upstream product

• 108-24-7 acetic anhydride 
• 108-46-3 recorcinol 
• 75-36-5 acetyl chloride 
• 108-58-7 Resorcinol diacetate 
• 144152-28-3 2,6-diacetoxyacetophenone 
• 4056-73-9 2-acetyl-1,3-cyclohexanedione 
• 7783-06-4 hydrogen sulfide 
• 95-50-1 1,2-dichloro-benzene 
• 1795-39-7 NSC 251156 
• 16932-49-3 2,6-dimethoxybenzonitrile 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 57234-29-4 1,3-bis(methoxymethyl)resorcinol 
• 76434-54-3 2',6'-bis(methoxymethoxy)acetophenone 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 25205-34-9 2,6-dihydroxy-3-nitroacetophenone 
• 56358-73-7 1-(2,3-dihydroxy-6-methoxy-phenyl)-ethanone 
• 107415-78-1 3-acetyl-2,4-dihydroxybenzoic acid 
• 58124-15-5 2',6'-bis(4-methoxybenzoyloxy)acetophenone 
• 6665-76-5 5-acetoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 88856-50-2 5-hydroxy-4'-methoxy-3-(4''-methoxybenzoyl)flavone 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 4047-24-9 1-[2-(benzyloxy)-6-hydroxyphenyl]ethanone 
• 3886-19-9 1-[2',6'-bis(phenylmethoxy)phenyl]ethanone 
• 69079-91-0 1-[2-Hydroxy-6-(4-phenoxy-butoxy)-phenyl]-ethanone 
• 69079-93-2 1-[2-Hydroxy-6-(3-phenyl-propoxy)-phenyl]-ethanone 
• 16130-20-4 1-(2-Acetyl-3-hydroxyphenoxy)-5-(4-acetyl-3-hydroxyphenoxy)pentan 
• 16130-01-1 1-{2-[5-(2-Acetyl-3-hydroxy-phenoxy)-pentyloxy]-6-hydroxy-phenyl}-ethanone 

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