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2-Hydroxychavicol
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Name

2-Hydroxychavicol

 EINECS N/A
CAS No. 1126-61-0 Density 1.148 g/cm3
PSA 40.46000 LogP 1.82630
Solubility N/A 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 N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 1126-61-0 (3,4-DIHYDROXY-ALLYLBENZENE) Hazard Symbols N/A
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;

Article Data 47

2-Hydroxychavicol Synthetic route

C21H18O2Si

1126-61-0

4-allylpyrocatechol

Conditions
ConditionsYield
With water100%
97-53-0

4-allylguaiacol

1126-61-0

4-allylpyrocatechol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With caesium carbonate In 2,2,2-trifluoroethanol for 24h; Irradiation;47%
93-28-7

eugenol acetate

1126-61-0

4-allylpyrocatechol

Conditions
ConditionsYield
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%

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

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