1126-61-0

Basic information

• Product Name: 3,4-DIHYDROXY-ALLYLBENZENE
• Synonyms: 2-hydroxychavicol;HYDROXYCHAVICOL;4-Allylpyrocatechol;1,2-Benzenediol, 4-(2-propen-1-yl)-;HYDROXYCHAVICOL(P);1,2-Dihydroxy-4-allylbenzene;4-(2-Propenyl)-1,2-benzenediol;4-Allyl-1,2-benzenediol
• CAS NO: 1126-61-0
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Mol File: 1126-61-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 42.0 to 46.0 °C
• Boiling Point: 123°C/2mmHg(lit.)
• Flash Point: 141℃
• Appearance: /
• Density: 1.148 g/cm³
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C
• PKA: 9.83±0.10(Predicted)
• BRN: 1937030
• CAS DataBase Reference: 3,4-DIHYDROXY-ALLYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDROXY-ALLYLBENZENE(1126-61-0)
• EPA Substance Registry System: 3,4-DIHYDROXY-ALLYLBENZENE(1126-61-0)

Safety Data

• WGK Germany: 3
• RTECS: CZ9029440
• Hazardous Substances Data: 1126-61-0(Hazardous Substances Data)

Usage

Chemical Properties

White to Gray to Brown powder to crystal.

Uses

4-Allylpyrocatechol (other name: hydroxychavicol), isolated from Piper betle leaves, has been reported as an antimicrobial, antioxidant, and anti-inflammatory agent. In 2009, it was reported as a more potent xanthine oxidase (XO) inhibitor than allopurinol, which is clinically used for the treatment of hyperuricemia.4-Allylpyrocatechol is an antioxidant found in Piper Betel leaf extract. It is widely used as mouth freshener. It is a phenolic compound, considered to be effective against indomethacin-gastropathy.

Preparation

4-allylpyrocatechol is readily obtained from precursors such as eugenol or methyl eugenol – two natural products predominately extracted from the essential oils of Syzygium aromaticum flower buds (commonly known as clove buds) by hydrodistillation.8.00 g EugTES (21 mmol) was dissolved in 10 mL of THF and purged with N2 for 45 minutes. The solution was then transferred, under N2, to a reaction vessel containing HCl solution, and mixed rapidly. The reaction proceeded quickly and completion was confirmed via thin layer chromatography. The organic layer was extracted into CH2Cl2 and then washed with H2O, followed by drying and filtration. The solvent was removed via vacuum to recover the pure product as a white solid (Yield, 54%).Synthesis of 4-allylpyrocatechol (EugOH) from methyl eugenol.

InChI:InChI=1/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2

Synthetic route

C21H18O2Si → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With water	100%

4-allylguaiacol (97-53-0) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With pyridine; aluminium(III) iodide In acetonitrile at 80℃; for 18h; Reagent/catalyst; Solvent;	99%
Stage #1: 4-allylguaiacol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; Reagent/catalyst;	99%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h; Reagent/catalyst;	99%

1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;	99%
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;	96%
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;	96%

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78℃; for 1h; dealkylation;	88%
With boron trifluoride diethyl etherate In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;	55.1%
With boron tribromide In dichloromethane at -78 - 0℃; for 1h;	27%

((4-allyl-1,2-phenylene)bis(oxy))bis(triethylsilane) (1414854-49-1) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;	70%
With hydrogenchloride In tetrahydrofuran; water at 20℃; Inert atmosphere;	54%

ortoquinone (583-63-1) + allyltributylstanane (24850-33-7) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78℃;	62%

2-allyloxyphenol (1126-20-1) → 4-allylpyrocatechol (1126-61-0) + 3-(2-propenyl)-1,2-benzenediol (1125-74-2)

Conditions	Yield
at 170℃; Inert atmosphere; Neat (no solvent);	A 18% B 54%
at 170℃; for 2h; Inert atmosphere;	A 18% B 54%
In neat (no solvent) at 170℃; for 3h; Claisen Rearrangement; Inert atmosphere; Sealed tube;	A 27% B 40%

benzene-1,2-diol (120-80-9) + 3-chloroprop-1-ene (107-05-1) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With sodium carbonate; copper(l) chloride In water at 20℃; for 0.5h;	54%

4-chloro-1,2-benzenediol (2138-22-9) + allyl-trimethyl-silane (762-72-1) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With caesium carbonate In 2,2,2-trifluoroethanol for 24h; Irradiation;	47%

eugenol acetate (93-28-7) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;	27%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;	27%

methyl magnesium iodide (917-64-6) + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With diethyl ether; xylene at 175 - 180℃; Erhitzen des vom Aether befreiten Reaktionsgemisches unter Stickstoff;

2-allyloxyphenol (1126-20-1) → 4-allylpyrocatechol (1126-61-0)

tetrachloromethane (56-23-5) + diethyl ether (60-29-7) + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) + 2 mol methyl magnesium iodide → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
Erhitzen des vom Aether befreiten Reaktionsgemisches auf 160-180grad;

caffeoyl alcohol (3598-26-3) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Larrea tridentata cinnamyl alcohol acyltransferase-1 / aq. buffer / 0.5 h / 30 °C / pH 7.9 / Enzymatic reaction 2: NADH; propenylphenol synthase from Larrea tridentata / aq. buffer / 30 °C / pH 6.5 View Scheme

caffeyl 9-acetate → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With propenylphenol synthase from Larrea tridentata; NADH In aq. buffer at 30℃; pH=6.5; Kinetics;

benzene-1,2-diol (120-80-9) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 1 h / 20 °C 1.2: 5.5 h / 20 - 70 °C 2.1: 2 h / 170 °C / Inert atmosphere View Scheme

4-allylguaiacol (97-53-0) → 4-allylpyrocatechol (1126-61-0) + 4-(2-iodopropyl)catechol

Conditions	Yield
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h; Reagent/catalyst;
With aluminium(III) iodide; N,N-dimethyl-formamide In acetonitrile at 80℃; for 18h; Reagent/catalyst;

benzene-1,2-diol (120-80-9) → 4-allylpyrocatechol (1126-61-0) + 3-(2-propenyl)-1,2-benzenediol (1125-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.5 h / 20 °C 1.2: 3.5 h / Reflux 2.1: neat (no solvent) / 3 h / 170 °C / Inert atmosphere; Sealed tube View Scheme

4-allylguaiacol (97-53-0) + diphenylsilane (775-12-2) → 4-allylpyrocatechol (1126-61-0)

Conditions	Yield
With tris(pentafluorophenyl)borate

4-allylpyrocatechol (1126-61-0) → 4-propylbenzene-1,2-diol (2525-02-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 1h; Inert atmosphere;	100%
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 2h;	95%
With methanol; palladium 10% on activated carbon at 20℃; for 2h;	95%
With triphenyl phosphite; hydrogen In chloroform at 25℃; Rate constant; Mechanism;
With hydrogen; palladium on activated charcoal In ethanol; trifluoroacetic acid for 24h; Hydrogenation;

4-allylpyrocatechol (1126-61-0) + acetic anhydride (108-24-7) → 4-allyl-1,2-phenylene diacetate (13620-82-1)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 2h;	97%
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	89%
With pyridine
With triethylamine In dichloromethane

4-allylpyrocatechol (1126-61-0) + benzyl bromide (100-39-0) → 3-[3,4-bis(benzyloxy)phenyl]prop-1-ene (857579-67-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;	93%

4-allylpyrocatechol (1126-61-0) + propargyl bromide (106-96-7) → 5-allyl-2-(prop-2-yn-1-yloxy)phenol

Conditions	Yield
Stage #1: 4-allylpyrocatechol With carbonate salt In acetone Inert atmosphere; Stage #2: propargyl bromide In acetone Inert atmosphere;	92%

d(4)-methanol (811-98-3) + 4-allylpyrocatechol (1126-61-0) → 4-allyl-1,2-di(methoxy-d3)benzole

Conditions	Yield
Stage #1: d(4)-methanol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: 4-allylpyrocatechol In tetrahydrofuran at 0 - 20℃; for 0.5h; Mitsunobu Displacement; Inert atmosphere;	86%

4-allylpyrocatechol (1126-61-0) + tert-butyldimethylsilyl chloride (18162-48-6) → ((4-allyl-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane) (854737-59-0)

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;	81%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 25℃; for 16h; Inert atmosphere;	75%
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃;	63%

4-allylpyrocatechol (1126-61-0) + 6-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)-7H-chromen-7-one → santarubin B (37381-57-0)

Conditions	Yield
With air In methanol; acetonitrile at 80℃; for 10h;	74%

4-allylpyrocatechol (1126-61-0) + coniferal alcohol (458-35-5, 32811-40-8, 69056-21-9) → C19H20O5 (1309608-05-6)

Conditions	Yield
With silver(l) oxide In acetone; benzene for 24h; hetero-Diels-Alder reaction;	73%

4-allylpyrocatechol (1126-61-0) + bromoacetic acid methyl ester (96-32-2) → dimethyl 2,2'-[(4-allyl-1,2-phenylene)-bis(oxy)]diacetate (362467-76-3)

Conditions	Yield
With sodium methylate In methanol for 16h; Williamson reaction; Heating;	65%

4-allylpyrocatechol (1126-61-0) + 1,3-Dichloroacetone (534-07-6) → 7-allylbenzo[b][1,4]dioxepin-3-one

Conditions	Yield
	61.3%
With potassium carbonate; sodium iodide In acetone for 4h; Heating;

4-allylpyrocatechol (1126-61-0) + coniferol (458-35-5) → 6-allyl-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan (74741-32-5)

Conditions	Yield
In acetone; benzene for 20h; Ambient temperature;	50%

4-allylpyrocatechol (1126-61-0) + diazomethyl-trimethyl-silane (18107-18-1) → chavibetol (501-19-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile at 0 - 20℃;	46%

4-allylpyrocatechol (1126-61-0) → 3-(3',4'-dihydroxyphenyl)-1-propanol (46118-02-9)

Conditions	Yield
Stage #1: 4-allylpyrocatechol With dimethylsulfide borane complex In tetrahydrofuran at -10 - 20℃; for 1.25h; Inert atmosphere; Stage #2: With sodium perborate hexahydrate In tetrahydrofuran; water at 20℃; for 2h;	35.1%

4-allylpyrocatechol (1126-61-0) + allyl bromide (106-95-6) → 4-allyl-5-propylbenzene-1,2-diol (1234378-77-8) + 3-allyl-4-propylbenzene-1,2-diol (1234378-87-0)

Conditions	Yield
Stage #1: 4-allylpyrocatechol With potassium carbonate In acetone for 1.5h; Stage #2: allyl bromide In acetone Reflux;	A 15% B 20.58%

diiodomethane (75-11-6) + 4-allylpyrocatechol (1126-61-0) → 1-allyl-3,4-methylenedioxybenzene (94-59-7)

Conditions	Yield
With potassium carbonate; acetone

4-allylpyrocatechol (1126-61-0) → 4-allyl-1,2-bis-benzoyloxy-benzene

4-allylpyrocatechol (1126-61-0) + benzyl chloride (100-44-7) → 3-[3,4-bis(benzyloxy)phenyl]prop-1-ene (857579-67-0)

Conditions	Yield
With potassium carbonate; acetone

4-allylpyrocatechol (1126-61-0) + benzoyl chloride (98-88-4) → 4-allyl-1,2-bis-benzoyloxy-benzene

Conditions	Yield
With alkali

4-allylpyrocatechol (1126-61-0) + chloroacetic acid (79-11-8) → (5-allyl-2-hydroxy-phenoxy)-acetic acid (99865-65-3)

Conditions	Yield
With potassium hydroxide

Upstream product

• 917-64-6 methyl magnesium iodide 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 1126-20-1 2-allyloxyphenol 
• 56-23-5 tetrachloromethane 
• 60-29-7 diethyl ether 
• 3598-26-3 caffeoyl alcohol 
• 120-80-9 benzene-1,2-diol 
• 107-05-1 3-chloroprop-1-ene 
• 93-28-7 eugenol acetate 
• 97-53-0 4-allylguaiacol 
• 775-12-2 diphenylsilane 
• 1414854-49-1 ((4-allyl-1,2-phenylene)bis(oxy))bis(triethylsilane) 
• 2138-22-9 4-chloro-1,2-benzenediol 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 857579-67-0 3-[3,4-bis(benzyloxy)phenyl]prop-1-ene 
• 99865-65-3 (5-allyl-2-hydroxy-phenoxy)-acetic acid 
• 362467-76-3 dimethyl 2,2'-[(4-allyl-1,2-phenylene)-bis(oxy)]diacetate 
• 854737-59-0 ((4-allyl-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane) 
• 1028377-50-5 3,4-bis[4-hydroxy-5-oxo-6-peroxycyclohexa-1,3-dienyl]hexa-1,5-diene 
• 5707-55-1 3,4-Dihydroxyphenylacetaldehyde 
• 1309608-07-8 C₂₁H₂₄O₈ 
• 1309608-09-0 C₃₅H₄₂O₁₄ 
• 1309608-12-5 C₃₃H₃₈O₁₂ 
• 1309608-13-6 C₃₃H₃₈O₁₂ 
• 1309608-17-0 C₃₃H₃₈O₁₂ 
• 322725-66-6 C₂₅H₂₂O₉ 
• 322725-65-5 C₂₅H₂₂O₉ 

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