Product Name

  • Name

    Ethyl 3,4-dihydroxybenzoate

  • EINECS 223-529-0
  • CAS No. 3943-89-3
  • Article Data34
  • CAS DataBase
  • Density 1.294 g/cm3
  • Solubility Insoluble in water. Soluble in ethanol.
  • Melting Point 132-134 °C(lit.)
  • Formula C9H10O4
  • Boiling Point 358.1 °C at 760 mmHg
  • Molecular Weight 182.176
  • Flash Point 147 °C
  • Transport Information
  • Appearance pale yellow to beige crystalline powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3943-89-3 (Ethyl 3,4-dihydroxybenzoate)
  • Hazard Symbols IrritantXi
  • Synonyms Protocatechuicacid, ethyl ester (7CI,8CI);3,4-Dihydroxybenzoic acid ethyl ester;Ethyl protocatechuate;NSC 619681;NSC 86130;
  • PSA 66.76000
  • LogP 1.27450

Synthetic route

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

ethanol
64-17-5

ethanol

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With sulfuric acid Heating;99%
With sulfuric acid at 50℃; for 3h;98%
With sulfuric acid98%
4-Benzyloxy-3-(4-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester

4-Benzyloxy-3-(4-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;96%
ethyl vanillate
617-05-0

ethyl vanillate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; Reagent/catalyst;94%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; Reagent/catalyst;94%
With aluminium(III) iodide; ethyl acetate; diisopropyl-carbodiimide In acetonitrile at 20℃; for 2h; chemoselective reaction;93%
4-Benzyloxy-3-(3-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester

4-Benzyloxy-3-(3-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;93%
4-benzyloxy-3-(4-nitro-benzyloxy)-benzoic acid ethyl ester

4-benzyloxy-3-(4-nitro-benzyloxy)-benzoic acid ethyl ester

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal at 20℃; for 3h;92%
ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate
20986-39-4

ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With aluminum (III) chloride In benzene for 1h; Reflux;90%
ethyl 4-oxocyclohexane-1-carboxylate
17159-79-4

ethyl 4-oxocyclohexane-1-carboxylate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;84%
ethanol
64-17-5

ethanol

4-(hydroxymethyl)benzene-1,2-diol
3897-89-0

4-(hydroxymethyl)benzene-1,2-diol

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With dihydrogen peroxide for 3h; Irradiation;83%
C17H28O4Si
1344113-41-2

C17H28O4Si

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
Stage #1: C17H28O4Si With palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene In α,α,α-trifluorotoluene at 120℃; Inert atmosphere;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;
Stage #3: With water In tetrahydrofuran		76%
ethyl 3-oxocyclohexanecarboxylate
33668-25-6

ethyl 3-oxocyclohexanecarboxylate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;53%
ethanol
64-17-5

ethanol

cyanidin 3-O-glucopyranoside chloride

cyanidin 3-O-glucopyranoside chloride

A

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

glucopyranosyl 2-(3,4-dihydroxyphenyl)-4,6-dihydroxybenzofuran-3-carboxylate

glucopyranosyl 2-(3,4-dihydroxyphenyl)-4,6-dihydroxybenzofuran-3-carboxylate

C

C15H10O7
1577235-12-1

C15H10O7

Conditions
ConditionsYield
With 2,2'-azobis-(2,4-dimethylvaleronitrile) at 60℃; for 4h;A 33%
B 28.2%
C 9.6%
...Expand
hydrogenchloride
7647-01-0

hydrogenchloride

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

ethanol
64-17-5

ethanol

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

...Expand
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

concentrated H2 SO4

concentrated H2 SO4

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
In ethanol39 g (69%)
In ethanol39 g (69%)
In ethanol39 g (69%)
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1H-imidazole / tetrahydrofuran / 20 °C / Inert atmosphere
1.3: 20 °C
2.1: palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene / α,α,α-trifluorotoluene / 120 °C / Inert atmosphere
2.2: 20 °C
View Scheme
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

A

sorbic Acid
110-44-1

sorbic Acid

B

formic acid
64-18-6

formic acid

C

glyceric acid
473-81-4

glyceric acid

D

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

E

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

benzene-1,2-diol

F

hydroquinone
123-31-9

hydroquinone

G

phenol
108-95-2

phenol

H

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; titanium(IV) oxide In water at 35℃; for 0.5h; pH=7.3; Concentration; Irradiation;
...Expand
ethanol
64-17-5

ethanol

cyanidin-3-O-glucoside

cyanidin-3-O-glucoside

A

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

B

C15H10O7
1577235-12-1

C15H10O7

C

C21H20O12

C21H20O12

Conditions
ConditionsYield
With water; dihydrogen peroxide at 40℃; for 2h;
...Expand
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone at 60℃; for 19h; Inert atmosphere;100%
With potassium carbonate In acetone at 20 - 70℃; for 24h;93%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 64h; Inert atmosphere; Reflux;93%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

ethyl 8-hydroxy-2,3-dimethyl-7-oxo-1,4,4a,7-tetrahydronaphthalene-4a-carboxylate

ethyl 8-hydroxy-2,3-dimethyl-7-oxo-1,4,4a,7-tetrahydronaphthalene-4a-carboxylate

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;98%
With tetradecafluorohexane; lithium perfluorooctane sulfonate; acetic acid Diels-Alder reaction; Electrochemical reaction;95%
In acetic acid electrochemical reaction: glass carbon anode (60x20 mm) coated with modified Nafion resin, Pt cathode (10x10 mm), aq. sodium dodecyl sulfate as supporting electrolyte, undivided cell 2.2 F mol-1, 0.8 V vs SCE; Yield given;
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

ethyl 3,4-bis(methoxymethoxy)benzoate
959146-62-4

ethyl 3,4-bis(methoxymethoxy)benzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 48h;98%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

isopropyl bromide
75-26-3

isopropyl bromide

ethyl 3,4-diisopropoxybenzoate
1369403-22-4

ethyl 3,4-diisopropoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 19h; Inert atmosphere;98%
Tetrafluorophthalonitrile
1835-65-0

Tetrafluorophthalonitrile

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

C26H16N2O8

C26H16N2O8

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 3h;98%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl (E)-4-methyl-3,5-hexadienoate
76200-27-6

ethyl (E)-4-methyl-3,5-hexadienoate

4-ethoxycarbonylmethyl-8-hydroxy-3-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

4-ethoxycarbonylmethyl-8-hydroxy-3-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In nitromethane for 16h; Ambient temperature; constant potential electrolysis on PTFE-fiber coated glassy carbon anode/Pt cathode (1200 mV vs. SCE);97%
1-bromo dodecane
112-29-8

1-bromo dodecane

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl 3,4-bis(dodecyloxy)benzoate
773135-90-3

ethyl 3,4-bis(dodecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide97%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

C25H26O6
1401529-49-4

C25H26O6

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;97%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

C9H8O4(2-)*Mg(2+)

C9H8O4(2-)*Mg(2+)

Conditions
ConditionsYield
With magnesium hydroxide In water at 20℃; for 2h;97%
ethyl (E)-3,5-hexadienoate
74054-58-3

ethyl (E)-3,5-hexadienoate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

4-ethoxycarbonylmethyl-8-hydroxy-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

4-ethoxycarbonylmethyl-8-hydroxy-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In nitromethane for 16h; Ambient temperature; constant potential electrolysis on PTFE-fiber coated glassy carbon anode/Pt cathode (1200 mV vs. SCE);96%
Dichlorodiphenylmethane
2051-90-3

Dichlorodiphenylmethane

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

2,2-Diphenyl-1,3-benzodioxolane-5-carboxylic acid, ethyl ester
152361-07-4

2,2-Diphenyl-1,3-benzodioxolane-5-carboxylic acid, ethyl ester

Conditions
ConditionsYield
at 170℃; for 0.166667h;95%
2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With 4-(Methylamino)pyridine; potassium carbonate at 90 - 95℃; Temperature; Reagent/catalyst;95%
With carbon dioxide; ammonia at 50℃; for 0.5h; Temperature; Reagent/catalyst;94.6%
With potassium tert-butylate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12h;87%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 120h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 9h;95 %Chromat.
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

3,4-bis-tert-butoxycarbonyloxy-benzoic acid ethyl ester
918402-89-8

3,4-bis-tert-butoxycarbonyloxy-benzoic acid ethyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;95%
thiophosgene
463-71-8

thiophosgene

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl 2-thioxobenzo[d][1,3]dioxole-5-carboxylate
33373-19-2

ethyl 2-thioxobenzo[d][1,3]dioxole-5-carboxylate

Conditions
ConditionsYield
With sodium carbonate In water at 0 - 20℃;95%
With dmap; carbon dioxide In dichloromethane; acetone at -78 - 20℃; for 19h;51%
2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride
538371-55-0

2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl 3,4-bis-(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzoate
916817-35-1

ethyl 3,4-bis-(2-(2-(2-ethoxyethoxy)ethoxy)ethoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide95%
1-[2-(ethoxy)ethoxy]-2-chloroethane
41771-35-1

1-[2-(ethoxy)ethoxy]-2-chloroethane

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl 3,4-bis-[2-(2-ethoxyehtoxy)ethoxy]benzoate
906550-98-9

ethyl 3,4-bis-[2-(2-ethoxyehtoxy)ethoxy]benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide95%
2-methoxyethyl methanesulfonate
16427-44-4

2-methoxyethyl methanesulfonate

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In toluene for 6h; Reflux;95%
With potassium tert-butylate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 30 - 40℃; for 10h;90.5%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

hexa(ethyleneglycol) ditosylate
42749-27-9

hexa(ethyleneglycol) ditosylate

C21H32O9

C21H32O9

Conditions
ConditionsYield
With potassium hexafluorophosphate; potassium carbonate In acetonitrile for 12h; Reflux;95%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

dimethyl sulfate
77-78-1

dimethyl sulfate

ethyl veratrate
3943-77-9

ethyl veratrate

Conditions
ConditionsYield
Stage #1: Ethyl protocatechuate With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: dimethyl sulfate at 50℃; for 5h;		94.5%
1-vinylcyclohexene
2622-21-1

1-vinylcyclohexene

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

ethyl 2,4a,4b,5,6,7,8,10-octahydro-1-hydroxy-2-oxophenanthrene-4a carboxylate
1196885-37-6

ethyl 2,4a,4b,5,6,7,8,10-octahydro-1-hydroxy-2-oxophenanthrene-4a carboxylate

Conditions
ConditionsYield
With lead(II,IV) oxide; trifluoroacetic acid In tetrahydrofuran at 20℃; for 2.5h;94%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

4’-[(10-bromodecyl)oxy]-4-carbonitrile-[1,1’-biphenyl]
140713-89-9

4’-[(10-bromodecyl)oxy]-4-carbonitrile-[1,1’-biphenyl]

3,4-bis[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester
610785-23-4

3,4-bis[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In butanone Heating;93%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

rhodamine B
509-34-2

rhodamine B

C28H30O3N2*C9H10O4

C28H30O3N2*C9H10O4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2.5h;93%
1-methylbuta-1,3-diene
2004-70-8

1-methylbuta-1,3-diene

Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

(4S,4aR)-8-Hydroxy-4-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

(4S,4aR)-8-Hydroxy-4-methyl-7-oxo-1,7-dihydro-4H-naphthalene-4a-carboxylic acid ethyl ester

Conditions
ConditionsYield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;92%
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate
20986-39-4

ethyl 3,4-dihydro-2H-benzo[b]1,4-dioxepine-7-carboxylate

Conditions
ConditionsYield
With potassium carbonate In ethanol for 5h; Reflux;91%

Ethyl 3,4-dihydroxybenzoate Chemical Properties

IUPAC Name: Ethyl 3,4-dihydroxybenzoate
Molecular Formula: C9H10O4
Molecular Weight: 182.173300 g/mol
Appearance: Pale yellow to beige crystalline powder
Density: 1.294 g/cm3
Melting Point: 131-136 °C
Boiling Point: 358.1 °C at 760 mmHg
Flash Point: 147 °C
Solubility: Ethanol
Insolubility: Water
BRN: 2097435
EINECS: 223-529-0
Synonyms of Ethyl 3,4-dihydroxy benzoate (CAS NO. 3943-89-3):
 Ethyl protocatechuate ; Benzoic acid, 3,4-dihydroxy-, ethyl ester (9CI) ; Ethyl 3,4-dihydroxybenzoate
Categories of Ethyl 3,4-dihydroxy benzoate (CAS NO. 3943-89-3):
FINE Chemical & INTERMEDIATES;Aromatic Esters;Benzoic acid;Organic acids;API intermediates

Ethyl 3,4-dihydroxybenzoate Uses

  Ethyl 3,4-dihydroxy benzoate , with cas registry number of 3943-89-3, is used as a food additive, pharmaceutical intermediate, etc.

Ethyl 3,4-dihydroxybenzoate Production

 Ethyl 3,4-dihydroxy benzoate (CAS NO.3943-89-3) can be obtained with the 3,4-hydroxy benzoic acid and alcohol by esterification.

Ethyl 3,4-dihydroxybenzoate Safety Profile

Safety Information of Ethyl 3,4-dihydroxy benzoate (CAS NO. 3943-89-3):
Hazard Codes: Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
37/39:Wear suitable gloves and eye/face protection
WGK Germany: 3
Hazard Note: Irritant

Ethyl 3,4-dihydroxybenzoate Specification

 It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition,  Ethyl 3,4-dihydroxy benzoate (CAS NO.3943-89-3) is not compatible with strong oxidizing agents, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.

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