1,2-Benzenediol,4-ethenyl- supplier

Name
3,4-dihydroxystyrene
EINECS
CAS No. 6053-02-7
Article Data27
CAS DataBase
Density 1.213 g/cm³
Solubility
Melting Point 50-53 °C
Formula C₈H₈O₂
Boiling Point 275.5 °C at 760 mmHg
Molecular Weight 136.15
Flash Point 136.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyrocatechol,4-vinyl- (7CI,8CI);3,4-Dihydroxystyrene;3,4-Styrenediol;4-Vinylcatechol;4-Vinylpyrocatechol;Vinylcatechol;
PSA 40.46000
LogP 1.74080

Synthetic route

: 331-39-5
caffeic acid

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
With cucumber juice at 30 - 35℃; for 24h; Inert atmosphere; Green chemistry;	98%
With Cocos nucifera juice at 20℃; for 48h; Inert atmosphere;	93%
With aluminum oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinone In methanol for 0.25h; microwave irradiation;	35%

: 141-82-2
malonic acid

: 139-85-5
3,4-dihydroxybenzaldehyde

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
With 10H-phenothiazine; diethylamine In N,N-dimethyl-formamide at 60℃; for 6h;	91.3%
With pyridine; acetic acid at 130℃; for 0.133333h; microwave irradiation;	55%
With piperidine; ethanol
With piperidine In ethanol for 8h; Heating;

: 139-85-5
3,4-dihydroxybenzaldehyde

: 105-53-3
diethyl malonate

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
With 10H-phenothiazine; diisopropylamine In N,N-dimethyl-formamide; toluene at 70℃; for 15h;	89.3%

: 2065-66-9
methyl-triphenylphosphonium iodide

: 139-85-5
3,4-dihydroxybenzaldehyde

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran for 1h; Inert atmosphere; Stage #2: 3,4-dihydroxybenzaldehyde In tetrahydrofuran at 25℃; for 24h; Wittig reaction; Inert atmosphere;	59.9%
With potassium tert-butylate In tetrahydrofuran Wittig Olefination;
With potassium tert-butylate In tetrahydrofuran Wittig Olefination;

: 331-39-5
caffeic acid

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride at 240℃; for 0.5h;	10%
Stage #1: caffeic acid In N,N-dimethyl-formamide at 80℃; for 18h; Stage #2: With 10H-phenothiazine In N,N-dimethyl-formamide at 60℃; Temperature;

: 124889-68-5
5-vinyl-benzo[1,3]dioxol-2-one

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
With pyridine

: 124889-68-5
5-vinyl-benzo[1,3]dioxol-2-one

aqueous pyridine solution: aqueous pyridine solution

: 6053-02-7
3,4-dihydroxystyrene

: 331-39-5
caffeic acid

A: 99-50-3
3,4-Dihydroxybenzoic acid

B: 305-01-1
aesculetin

C: 6053-02-7
3,4-dihydroxystyrene

D: 331-39-5
cis-caffeic acid

Conditions

Conditions	Yield
In water for 3.26667h; pH=6.5; Kinetics; Mechanism; pH-value; UV-irradiation;

...Expand

: 139-85-5
3,4-dihydroxybenzaldehyde

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: morpholine / N,N-dimethyl-formamide / 0.33 h / 18 - 25 °C 1.2: 22 h / 70 °C 2.1: N,N-dimethyl-formamide / 18 h / 80 °C 2.2: 60 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine; glycine / 2 h / 80 °C / 760.05 Torr 2: triethylamine / 8 h / 140 °C View Scheme

: 1779-49-3
Methyltriphenylphosphonium bromide

: 139-85-5
3,4-dihydroxybenzaldehyde

: 6053-02-7
3,4-dihydroxystyrene

Conditions

Conditions	Yield
Wittig Olefination;

: 6053-02-7
3,4-dihydroxystyrene

: AG 1233

Conditions

Conditions	Yield
Grubbs catalyst first generation In tetrahydrofuran for 1h; Heating;	92%
With Hoveyda-Grubbs catalyst second generation In tert-butyl methyl ether at 65℃; for 4h; Inert atmosphere; Schlenk technique;	37%

: 6053-02-7
3,4-dihydroxystyrene

: 75-36-5
acetyl chloride

: 57142-64-0
3,4-diacetoxystyrene

Conditions

Conditions	Yield
With 10H-phenothiazine; triethylamine In tert-butyl methyl ether at -5 - 20℃; for 1h; Green chemistry;	87.3%

: 23030-43-5
2,5-dihydroxy-1-iodobenzene

: 6053-02-7
3,4-dihydroxystyrene

: 1093198-97-0
(E)-2',3,4,5'-tetrahydroxystilbene

Conditions

Conditions	Yield
With triethanolamine; palladium diacetate at 100℃; for 24h; Inert atmosphere;	62.4%
With triethanolamine; palladium diacetate at 100℃; for 24h; Mizoroki-Heck reaction; Inert atmosphere;	39.5%
With triethanolamine; palladium diacetate at 100℃; for 24h; Heck Reaction; Inert atmosphere;

: 75-09-2
dichloromethane

: 6053-02-7
3,4-dihydroxystyrene

: 7315-32-4
5-vinyl-1,3-benzodioxole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;	55%

: 6053-02-7
3,4-dihydroxystyrene

: 108-24-7
acetic anhydride

: 57142-64-0
3,4-diacetoxystyrene

Conditions

Conditions	Yield
With triethylamine In tert-butyl methyl ether; N,N-dimethyl-formamide at 10 - 20℃; for 4h;	37%
at 80℃; under 760.051 Torr; for 2h;	73.02 g

: 15155-41-6
4,7-dibromobenzo[c][1,2,5]thiadiazole

: 6053-02-7
3,4-dihydroxystyrene

: 620-18-8
3-hydroxystyrene

A: 4-((E)-2-(7-((E)-3-hydroxystyryl)benzo[c][1,2,5]thiadiazol-4-yl)vinyl)benzene-1,2-diol

B: 3,3'-((1E,1'E)-benzo[c][1,2,5]thiadiazole-4,7-diylbis(ethene-2,1-diyl))diphenol

Conditions

Conditions	Yield
With triethanolamine; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 24h; Heck Reaction; Inert atmosphere;	A 37% B 9%

...Expand

: 6053-02-7
3,4-dihydroxystyrene

: malvidin 3-glucoside hydrochloride

A: 7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-10-(3,4-dihydroxyphenyl)-pyrano[4,3,2-de]chromen-1-ylium-3-O-glucoside

B: 5-(3,4-Dihydroxy-phenyl)-8-hydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4,5-dihydro-pyrano[4,3,2-de]chromen-1-ylium

C: 4-[2-(3,4-Dihydroxy-phenyl)-ethyl]-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium

D: 4-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 20℃; for 168h; pH=1.5;	A 35% B n/a C n/a D n/a

...Expand

: 15155-41-6
4,7-dibromobenzo[c][1,2,5]thiadiazole

: 6053-02-7
3,4-dihydroxystyrene

: 2628-17-3
4-Vinylphenol

A: 4,4'-((1E,1'E)-benzo[c][1,2,5]thiadiazole-4,7-diylbis(ethene-2,1-diyl))bis(benzene-1,2-diol)

B: 4-((E)-2-(7-((E)-4-hydroxystyryl)benzo[c][1,2,5]thiadiazol-4- yl)vinyl)benzene-1,2-diol

Conditions

Conditions	Yield
With triethanolamine; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 24h; Heck Reaction; Inert atmosphere;	A 15% B 29%

...Expand

: 6053-02-7
3,4-dihydroxystyrene

: methyl 2-(7-bromo-2-oxobenzo[d]oxazol-3(2H)-yl)acetate

: methyl (E)-2-(7-(3,4-dihydroxystyryl)-2-oxobenzo[d]oxazol-3(2H)-yl)acetate

Conditions

Conditions	Yield
Stage #1: methyl 2-(7-bromo-2-oxobenzo[d]oxazol-3(2H)-yl)acetate With palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 20℃; for 0.5h; Heck Reaction; Inert atmosphere; Stage #2: 3,4-dihydroxystyrene With triethylamine In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;	17%

: 6053-02-7
3,4-dihydroxystyrene

: tris(4-vinyl-o-phenylenedioxy)cyclotriphosphazene

Conditions

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium carbonate In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;	9%

: 6053-02-7
3,4-dihydroxystyrene

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

Conditions

Conditions	Yield
under 12 Torr; beim Destillieren;

: 6053-02-7
3,4-dihydroxystyrene

: malvidin 3-O-glucopyranoside

: 7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-10-(3,4-dihydroxyphenyl)-pyrano[4,3,2-de]chromen-1-ylium-3-O-glucoside

Conditions

Conditions	Yield
In ethanol

: 1623-05-8
perfluoro(propyl vinyl ether)

: 6053-02-7
3,4-dihydroxystyrene

: 3,4-bis[2-(heptafluoropropoxy)-1,1,2-trifluoroethoxy]styrene

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide at 20 - 60℃; for 8h; Product distribution / selectivity; Hastelloy pressure vessel;
With potassium hydroxide In N,N-dimethyl acetamide at 20 - 44℃; Product distribution / selectivity;

: 6053-02-7
3,4-dihydroxystyrene

: 7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-10-(3,4-dihydroxyphenyl)-pyrano[4,3,2-de]chromen-1-ylium-3-O-glucoside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / acetonitrile; H2O / 168 h / 20 °C / pH 1.5 2: aq. HCl / 16 h / 45 °C / pH 1.5 View Scheme
Multi-step reaction with 2 steps 1: HCl / acetonitrile; H2O / 168 h / 20 °C / pH 1.5 2: aq. HCl / 16 h / 45 °C / pH 1.5 View Scheme
Multi-step reaction with 2 steps 1: HCl / acetonitrile; H2O / 168 h / 20 °C / pH 1.5 2: aq. HCl / 16 h / 45 °C / pH 1.5 View Scheme

: C8H8O3S

: 6053-02-7
3,4-dihydroxystyrene

: 865541-38-4
4-(5,7-dimethoxy-2,3-dihydro-benzo[1,4]oxathiin-2-yl)-benzene-1,2-diol

Conditions

Conditions	Yield
Diels-Alder reaction;

: C6H4O3S

: 6053-02-7
3,4-dihydroxystyrene

: 2-(3,4-dihydroxy-phenyl)-2,3-dihydro-benzo[1,4]oxathiine-5,7-diol

Conditions

Conditions	Yield
Diels-Alder reaction;

: 18470-06-9
malvidin 3-O-glucoside

: 6053-02-7
3,4-dihydroxystyrene

: malvidin-3-O-glucoside-4-vinylcatechol

Conditions

Conditions	Yield
In ethanol; water at 30℃; pH=3.5;

: 6053-02-7
3,4-dihydroxystyrene

: malvidin 3-(6''-O-p-coumaroyl)glucoside

: 703403-97-8, 1210935-94-6
C40H35O16(1+)

Conditions

Conditions	Yield
In ethanol; water at 30℃; pH=3.5;

: 6053-02-7
3,4-dihydroxystyrene

: 144017-65-2
(+)-Stiripentol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Heating; Enzymatic reaction View Scheme

: 994-30-9
triethylsilyl chloride

: 6053-02-7
3,4-dihydroxystyrene

: C20H36O2Si2

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Alkaline conditions;

1,2-Benzenediol,4-ethenyl- Specification

The 1,2-Benzenediol,4-ethenyl- is an organic compound with the formula C₈H₈O₂. The IUPAC name of this chemical is 4-ethenylbenzene-1,2-diol. With the CAS registry number 6053-02-7, it is also named as 4-Vinylbenzene-1,2-diol.

Physical properties about 1,2-Benzenediol,4-ethenyl- are: (1)ACD/LogP: 1.71; (2)ACD/LogD (pH 5.5): 1.71; (3)ACD/LogD (pH 7.4): 1.71; (4)ACD/BCF (pH 5.5): 11.77; (5)ACD/BCF (pH 7.4): 11.65; (6)ACD/KOC (pH 5.5): 203.21; (7)ACD/KOC (pH 7.4): 201.29; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 18.46 Å²; (12)Index of Refraction: 1.65; (13)Molar Refractivity: 40.94 cm³; (14)Molar Volume: 112.2 cm³; (15)Polarizability: 16.22×10^-24cm³; (16)Surface Tension: 52.5 dyne/cm; (17)Density: 1.213 g/cm³; (18)Flash Point: 136.5 °C; (19)Enthalpy of Vaporization: 53.46 kJ/mol; (20)Boiling Point: 275.5 °C at 760 mmHg; (21)Vapour Pressure: 0.00302 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(\C=C)cc1O
(2)InChI: InChI=1/C8H8O2/c1-2-6-3-4-7(9)8(10)5-6/h2-5,9-10H,1H2
(3)InChIKey: FBTSUTGMWBDAAC-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C8H8O2/c1-2-6-3-4-7(9)8(10)5-6/h2-5,9-10H,1H2
(5)Std. InChIKey: FBTSUTGMWBDAAC-UHFFFAOYSA-N

Product Name

3,4-dihydroxystyrene

Synthetic route

1,2-Benzenediol,4-ethenyl- Specification

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