Product Name

  • Name

    Protocatechualdehyde

  • EINECS 205-377-7
  • CAS No. 139-85-5
  • Article Data150
  • CAS DataBase
  • Density 1.409 g/cm3
  • Solubility Water solubility: 50 g/L (20 °C)
  • Melting Point 150-157 °C(lit.)
  • Formula C7H6O3
  • Boiling Point 295.4 °C at 760 mmHg
  • Molecular Weight 138.123
  • Flash Point 146.7 °C
  • Transport Information
  • Appearance brown powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 139-85-5 (Protocatechualdehyde)
  • Hazard Symbols IrritantXi
  • Synonyms 3,4-Dihydroxybenzenecarbonal;Rancinamycin IV;Benzaldehyde, 3,4-dihydroxy- (9CI);4-Formyl-1, 2-dihydroxybenzene;Benzaldehyde, 3,4-dihydroxy-;Protocatechualdehyde;Benzaldehyde,3,4-dihydroxy-;3,4-Dihydroxy Benzaldehyde;3,4-dihydroxyBenzaldehyde;protocatechualdehyde;
  • PSA 57.53000
  • LogP 0.91030

Synthetic route

vanillin
121-33-5

vanillin

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 4℃; for 1h;100%
With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane at 83.5℃; for 0.1h;99.3%
Stage #1: vanillin With boron tribromide-dimethyl sulfide complex In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With water In methanol; dichloromethane at 0℃; for 0.166667h; Inert atmosphere;		99%
isovanillin
621-59-0

isovanillin

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
Stage #1: isovanillin With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃;		99%
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;95%
piperonal
120-57-0

piperonal

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With boron trichloride - methyl sulfide complex In 1,2-dichloro-ethane at 83.5℃; for 29.5h; other reagent;98.5%
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 1.5h; Heating;84%
With titanium tetrachloride In dichloromethane at -20 - -10℃; for 4h; Inert atmosphere;68.4%
3,4-bis-methoxymethoxy-benzaldehyde
6515-06-6

3,4-bis-methoxymethoxy-benzaldehyde

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;98%
2-iodoisovanillin
138490-94-5

2-iodoisovanillin

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
In [(2)H6]acetone; dichloromethane96.1%
4-hydroxy-3-ethoxybenzaldehyde
121-32-4

4-hydroxy-3-ethoxybenzaldehyde

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
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;95%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h;93%
3,4-dihydroxyphenylacetate
102-32-9

3,4-dihydroxyphenylacetate

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 90℃; for 12h; Green chemistry;63%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
62.4%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

A

vanillin
121-33-5

vanillin

B

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Heating;A 58%
B 20%
3-hydroxy-4-methoxybenzyl alcohol
4383-06-6

3-hydroxy-4-methoxybenzyl alcohol

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
Stage #1: 3-hydroxy-4-methoxybenzyl alcohol With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In tetrahydrofuran at 20℃; Darkness;
Stage #2: With sodium dithionite; water In tetrahydrofuran Darkness;		56%
3,4-dihydroxy-5-iodobenzaldehyde
54246-05-8

3,4-dihydroxy-5-iodobenzaldehyde

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With silver; sodium hydrogencarbonate; sodium iodide; zinc In 1,2-dimethoxyethane; dimethyl sulfoxide at 80℃; for 6h;27%
methanol
67-56-1

methanol

caffeic acid
331-39-5

caffeic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

C

(E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime

(E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime

D

(E)-2-(3,4-dihydroxyphenyl)-2-methoxyethanaloxime

(E)-2-(3,4-dihydroxyphenyl)-2-methoxyethanaloxime

Conditions
ConditionsYield
With acetate buffer; sodium nitrite at 20℃; for 4h; pH=4; Further byproducts.;A 6%
B 9%
C 10%
D 5%
...Expand
D-erythrose
583-50-6

D-erythrose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

C

1-(3,4-dihydroxyphenyl)ethan-1-one
1197-09-7

1-(3,4-dihydroxyphenyl)ethan-1-one

D

1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one
55087-82-6

1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one

E

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

F

3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

Conditions
ConditionsYield
With acetate buffer for 45h; Product distribution; Heating;A 0.04%
B 0.03%
C 0.01%
D 0.15%
E 0.01%
F 0.03%
...Expand
methanol
67-56-1

methanol

4-benzenesulfonyloxy-3-hydroxy-benzaldehyde

4-benzenesulfonyloxy-3-hydroxy-benzaldehyde

sodium methylate
124-41-4

sodium methylate

A

vanillin
121-33-5

vanillin

B

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

...Expand
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

piperonal
120-57-0

piperonal

chloroform
67-66-3

chloroform

A

6-bromopiperonylic acid
60546-62-5

6-bromopiperonylic acid

B

6-bromo-3,4-methylenedioxybenzaldehyde
15930-53-7

6-bromo-3,4-methylenedioxybenzaldehyde

C

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
auch unter Zusatz von Dibenzoylperoxid;
...Expand
5-dichloromethyl-benzo[1,3]dioxol-2-one
866998-51-8

5-dichloromethyl-benzo[1,3]dioxol-2-one

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With water
With diluted acids
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

3-bromo-4-hydroxybenzylaldehyde
2973-78-6

3-bromo-4-hydroxybenzylaldehyde

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

D

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
at 160℃;
at 190℃;
...Expand
4-hydroxy-3-(methoxymethoxy)benzaldehyde
65298-98-8

4-hydroxy-3-(methoxymethoxy)benzaldehyde

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With sodium hydrogensulfite und anschliessendes Erhitzen mit wss.H2SO4;
With methanol; mineral acid
hexamethylenetetramine
100-97-0

hexamethylenetetramine

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

benzene-1,2-diol

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With p-dimethylaminonitrosobenzene
5-formyl-2-hydroxybenzaldehyde
3328-70-9

5-formyl-2-hydroxybenzaldehyde

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
3-bromo-4-hydroxybenzylaldehyde
2973-78-6

3-bromo-4-hydroxybenzylaldehyde

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
at 150 - 200℃; unter Druck;
benzyl chloride
100-44-7

benzyl chloride

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-dibenzyloxybenzaldehyde
5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h;100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 130℃; for 4h;96%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde
99815-16-4

3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 1h;99%
With 1H-imidazole In dichloromethane98%
1-bromo dodecane
112-29-8

1-bromo dodecane

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-didecyloxybenzaldehyde
118468-34-1

3,4-didecyloxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Williamson ether synthesis;100%
With potassium carbonate; potassium iodide In dichloromethane at 90℃; for 16h; Inert atmosphere;97%
Stage #1: 3,4-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide for 0.166667h;
Stage #2: 1-bromo dodecane In N,N-dimethyl-formamide at 100℃; for 12h;		91%
allyl bromide
106-95-6

allyl bromide

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-diallyloxybenzaldehyde
71186-67-9

3,4-diallyloxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;100%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 2h;98%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 2h;98%
3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

3,4-dihydroxybenzonitrile
17345-61-8

3,4-dihydroxybenzonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride In 1-methyl-pyrrolidin-2-one at 100℃; for 0.5h;100%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation;89%
With formic acid; hydroxylamine hydrochloride; silica gel for 0.0166667h; Irradiation;70 % Chromat.
1,3,5-tris(3-aminopropyl)adamantane
1029302-64-4

1,3,5-tris(3-aminopropyl)adamantane

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine
1448150-60-4

N,N′,N′′-tris(3,4-dihydroxybenzylidene)adamantane-1,3,5-tripropaneamine

Conditions
ConditionsYield
In ethanol for 24h; Inert atmosphere;100%
dimedone
126-81-8

dimedone

malononitrile
109-77-3

malononitrile

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

2-amino-4-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
326918-69-8

2-amino-4-(3,4-dihydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
With horsetail plant ash In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst;100%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane for 1.5h; Reflux;97%
With 1-methylimidazolium tricyanomethanide In neat (no solvent) at 20℃; for 0.333333h; Green chemistry;92%
With potassium carbonate In water at 20℃; for 1.16667h; Green chemistry;82%
With dmap at 150℃; for 0.333333h; Microwave irradiation;57%
...Expand
hydrogen cyanide
74-90-8

hydrogen cyanide

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

(R)-3,4-dihydroxymandelonitrile
190383-25-6

(R)-3,4-dihydroxymandelonitrile

Conditions
ConditionsYield
With (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica Lincz immobilized onto Eupergit CM In tert-butyl methyl ether; dimethyl sulfoxide at 5℃; for 72h; pH=4; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;100%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

malononitrile
109-77-3

malononitrile

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

6-amino-1,4-dihydro-4-(3,4-dihydroxyphenyl)-3methyl-pyran [2,3-c]pyrazole-5-carbonitrile

6-amino-1,4-dihydro-4-(3,4-dihydroxyphenyl)-3methyl-pyran [2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: ethyl acetoacetate With hydrazine hydrate; C10H21N2(1+)*C2H3O2(1-) at 60℃; for 0.0833333h;
Stage #2: malononitrile; 3,4-dihydroxybenzaldehyde In acetonitrile at 20 - 25℃; for 0.5h; Reagent/catalyst; Temperature;		100%
With hydrazine hydrate In ethanol; water for 0.666667h; Reflux; Green chemistry;82%
...Expand
3-[2-(4-hydroxyphenyl)ethyl]-2-thioxo-1,3-thiazolidin-4-one

3-[2-(4-hydroxyphenyl)ethyl]-2-thioxo-1,3-thiazolidin-4-one

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

5-(3,4-dihydroxybenzylidene)-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one

5-(3,4-dihydroxybenzylidene)-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one

Conditions
ConditionsYield
With ammonium acetate; acetic acid Reflux;100%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

5-(3,4-dihydroxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione
191167-05-2

5-(3,4-dihydroxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione

Conditions
ConditionsYield
In ethanol; water at 80℃; for 8h;99.3%
In ethanol; water at 80℃; for 8h;99.3%
With ammonium chloride In water at 20℃; for 0.5h;94%

3,4-Dihydroxybenzaldehyde Specification

3,4-Dihydroxybenzaldehyde, its cas register number is 139-85-5. It also can be called Protocatechualdehyde; Rancinamycin IV; and 4-Formyl-1,2-dihydroxybenzene. It is hazardous, so the first aid measures and others should be known. In addition, 3,4-Dihydroxybenzaldehyde could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.  3,4-Dihydroxybenzaldehyde is an important pharmaceutical intermediate, and can be used for synthesis of antibiotics and anti-inflammatory drugs.

Physical properties about 3,4-Dihydroxybenzaldehyde are: (1)ACD/LogP: 0.934; (2)ACD/LogD (pH 5.5): 0.93; (3)ACD/LogD (pH 7.4): 0.72; (4)ACD/BCF (pH 5.5): 2.99; (5)ACD/BCF (pH 7.4): 1.84; (6)ACD/KOC (pH 5.5): 76.12; (7)ACD/KOC (pH 7.4): 46.86; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)Index of Refraction: 1.674 ; (11)Molar Refractivity: 36.769 cm3; (12)Molar Volume: 97.959 cm3; (13)Polarizability: 14.576 10-24cm3; (14)Surface Tension: 69.0270004272461 dyne/cm; (15)Density: 1.41 g/cm3; (16)Flash Point: 146.695 °C; (17)Enthalpy of Vaporization: 55.655 kJ/mol; (18)Boiling Point: 295.418 °C at 760 mmHg; (19)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Wear suitable gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H;
(2)InChIKey=IBGBGRVKPALMCQ-UHFFFAOYSA-N;
(3)Smilesc1(cc(c(O)cc1)O)C=O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 205mg/kg (205mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Annales Pharmaceutiques Francaises. Vol. 15, Pg. 461, 1957.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07875,

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