2-Hydroxychavicol supplier | CasNO.1126-61-0

Name
3,4-DIHYDROXY-ALLYLBENZENE
EINECS
CAS No. 1126-61-0
Article Data47
CAS DataBase
Density 1.148 g/cm³
Solubility
Melting Point 42.0 to 46.0 °C
Formula C₉H₁₀O₂
Boiling Point 289.2 °C at 760 mmHg
Molecular Weight 150.177
Flash Point 141.7 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2-Benzenediol,4-(2-propenyl)- (9CI);Pyrocatechol, 4-allyl- (6CI,7CI,8CI);1,2-Dihydroxy-4-allylbenzene;1-Allyl-3,4-dihydroxybenzene;4-(2'-Propenyl)-1,2-benzenediol;4-Allyl-1,2-dihydroxybenzene;4-Allylcatechol;4-Allylpyrocatechol;Hydroxychavicol;
PSA 40.46000
LogP 1.82630

Synthetic route

: C21H18O2Si

: 1126-61-0
4-allylpyrocatechol

Conditions

Conditions	Yield
With water	100%

: 97-53-0
4-allylguaiacol

: 1126-61-0
4-allylpyrocatechol

Conditions

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%

: 93-15-2
1,2-dimethoxy-4-(2-propenyl)benzene

: 1126-61-0
4-allylpyrocatechol

Conditions

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%

: 94-59-7
1-allyl-3,4-methylenedioxybenzene

: 1126-61-0
4-allylpyrocatechol

Conditions

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%

: 1414854-49-1
((4-allyl-1,2-phenylene)bis(oxy))bis(triethylsilane)

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 583-63-1
ortoquinone

: 24850-33-7
allyltributylstanane

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 1126-20-1
2-allyloxyphenol

A: 1126-61-0
4-allylpyrocatechol

B: 1125-74-2
3-(2-propenyl)-1,2-benzenediol

Conditions

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%

: 120-80-9
benzene-1,2-diol

: 107-05-1
3-chloroprop-1-ene

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 2138-22-9
4-chloro-1,2-benzenediol

: 762-72-1
allyl-trimethyl-silane

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 93-28-7
eugenol acetate

: 1126-61-0
4-allylpyrocatechol

Conditions

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%

: 917-64-6
methyl magnesium iodide

: 93-15-2
1,2-dimethoxy-4-(2-propenyl)benzene

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 1126-20-1
2-allyloxyphenol

: 1126-61-0
4-allylpyrocatechol

: 56-23-5
tetrachloromethane

: 60-29-7
diethyl ether

: 93-15-2
1,2-dimethoxy-4-(2-propenyl)benzene

2 mol methyl magnesium iodide: 2 mol methyl magnesium iodide

: 1126-61-0
4-allylpyrocatechol

Conditions

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

...Expand

: 3598-26-3
caffeoyl alcohol

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 120-80-9
benzene-1,2-diol

: 1126-61-0
4-allylpyrocatechol

Conditions

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

: 97-53-0
4-allylguaiacol

A: 1126-61-0
4-allylpyrocatechol

B: 4-(2-iodopropyl)catechol

Conditions

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;

: 120-80-9
benzene-1,2-diol

A: 1126-61-0
4-allylpyrocatechol

B: 1125-74-2
3-(2-propenyl)-1,2-benzenediol

Conditions

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

: 97-53-0
4-allylguaiacol

: 775-12-2
diphenylsilane

: 1126-61-0
4-allylpyrocatechol

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate

: 1126-61-0
4-allylpyrocatechol

: 2525-02-2
4-propylbenzene-1,2-diol

Conditions

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;

: 1126-61-0
4-allylpyrocatechol

: 108-24-7
acetic anhydride

: 13620-82-1
4-allyl-1,2-phenylene diacetate

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 100-39-0
benzyl bromide

: 857579-67-0
3-[3,4-bis(benzyloxy)phenyl]prop-1-ene

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 106-96-7
propargyl bromide

: 5-allyl-2-(prop-2-yn-1-yloxy)phenol

Conditions

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

: 811-98-3
d(4)-methanol

: 1126-61-0
4-allylpyrocatechol

: 4-allyl-1,2-di(methoxy-d3)benzole

Conditions

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%

: 1126-61-0
4-allylpyrocatechol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 854737-59-0
((4-allyl-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane)

Conditions

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%

: 1126-61-0
4-allylpyrocatechol

: 6-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)-7H-chromen-7-one

: 37381-57-0
santarubin B

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

: 1309608-05-6
C19H20O5

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 96-32-2
bromoacetic acid methyl ester

: 362467-76-3
dimethyl 2,2'-[(4-allyl-1,2-phenylene)-bis(oxy)]diacetate

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 534-07-6
1,3-Dichloroacetone

: 7-allylbenzo[b][1,4]dioxepin-3-one

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 458-35-5
coniferol

: 74741-32-5
6-allyl-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 18107-18-1
diazomethyl-trimethyl-silane

: 501-19-9
chavibetol

Conditions

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

: 1126-61-0
4-allylpyrocatechol

: 46118-02-9
3-(3',4'-dihydroxyphenyl)-1-propanol

Conditions

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%

: 1126-61-0
4-allylpyrocatechol

: 106-95-6
allyl bromide

A: 1234378-77-8
4-allyl-5-propylbenzene-1,2-diol

B: 1234378-87-0
3-allyl-4-propylbenzene-1,2-diol

Conditions

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%

...Expand

: 75-11-6
diiodomethane

: 1126-61-0
4-allylpyrocatechol

: 94-59-7
1-allyl-3,4-methylenedioxybenzene

Conditions

Conditions	Yield
With potassium carbonate; acetone

: 1126-61-0
4-allylpyrocatechol

: 4-allyl-1,2-bis-benzoyloxy-benzene

: 1126-61-0
4-allylpyrocatechol

: 100-44-7
benzyl chloride

: 857579-67-0
3-[3,4-bis(benzyloxy)phenyl]prop-1-ene

Conditions

Conditions	Yield
With potassium carbonate; acetone

: 1126-61-0
4-allylpyrocatechol

: 98-88-4
benzoyl chloride

: 4-allyl-1,2-bis-benzoyloxy-benzene

Conditions

Conditions	Yield
With alkali

: 1126-61-0
4-allylpyrocatechol

: 79-11-8
chloroacetic acid

: 99865-65-3
(5-allyl-2-hydroxy-phenoxy)-acetic acid

Conditions

Conditions	Yield
With potassium hydroxide

2-Hydroxychavicol Specification

The 2-Hydroxychavicol, with the CAS registry number 1126-61-0, is also known as 1,2-Benzenediol, 4-(2-propenyl)-. This chemical's molecular formula is C₉H₁₀O₂ and molecular weight is 150.1745. Its systematic name is called 4-(prop-2-en-1-yl)benzene-1,2-diol.

Physical properties of 2-Hydroxychavicol: (1)ACD/LogP: 1.90; (2)ACD/LogD (pH 5.5): 1.9; (3)ACD/LogD (pH 7.4): 1.9; (4)ACD/BCF (pH 5.5): 16.3; (5)ACD/BCF (pH 7.4): 16.21; (6)ACD/KOC (pH 5.5): 256.64; (7)ACD/KOC (pH 7.4): 255.22; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.586; (12)Molar Refractivity: 43.92 cm³; (13)Molar Volume: 130.7 cm³; (14)Surface Tension: 47.2 dyne/cm; (15)Density: 1.148 g/cm³; (16)Flash Point: 141.7 °C; (17)Enthalpy of Vaporization: 54.97 kJ/mol; (18)Boiling Point: 289.2 °C at 760 mmHg; (19)Vapour Pressure: 0.00128 mmHg at 25°C.

Preparation of 2-Hydroxychavicol: this chemical can be prepared by 4-allyl-2-methoxy-phenol. This reaction will need reagents sodium iodide, silicon tetrachloride and solvents acetonitrile, toluene. The reaction time is 20 hours. The yield is about 62%.

2-Hydroxychavicol can be prepared by 4-allyl-2-methoxy-phenol. This reaction will need reagents sodium iodide, silicon tetrachloride and solvents acetonitrile, toluene

Uses of 2-Hydroxychavicol: it can be used to produce 6-allyl-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan at ambient temperature. This reaction will need solvents benzene and acetone with reaction time of 20 hours. The yield is about 50%.

2-Hydroxychavicol can be used to produce 6-allyl-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(cc1O)C\C=C
(2)InChI: InChI=1/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
(3)InChIKey: FHEHIXJLCWUPCZ-UHFFFAOYAL

Product Name

3,4-DIHYDROXY-ALLYLBENZENE

Synthetic route

2-Hydroxychavicol Specification

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