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139-85-5

Basic Information
CAS No.: 139-85-5
Name: 3,4-Dihydroxybenzaldehyde
Molecular Structure:
Molecular Structure of 139-85-5 (3,4-Dihydroxybenzaldehyde)
Formula: C7H6O3
Molecular Weight: 138.12
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;
EINECS: 205-377-7
Density: 1.409 g/cm3
Melting Point: 150-157 °C(lit.)
Boiling Point: 295.4 °C at 760 mmHg
Flash Point: 146.7 °C
Solubility: Water solubility: 50 g/L (20 °C)
Appearance: brown powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 57.53000
LogP: 0.91030
Synthetic route
121-33-5

vanillin

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%
621-59-0

isovanillin

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%
120-57-0

piperonal

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%
6515-06-6

3,4-bis-methoxymethoxy-benzaldehyde

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%
138490-94-5

2-iodoisovanillin

139-85-5

3,4-dihydroxybenzaldehyde

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

4-hydroxy-3-ethoxybenzaldehyde

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%
102-32-9

3,4-dihydroxyphenylacetate

139-85-5

3,4-dihydroxybenzaldehyde

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

benzene-1,2-diol

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
62.4%
120-14-9

3,4-dimethoxy-benzaldehyde

A

121-33-5

vanillin

B

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%
4383-06-6

3-hydroxy-4-methoxybenzyl alcohol

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%
54246-05-8

3,4-dihydroxy-5-iodobenzaldehyde

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%
67-56-1

methanol

331-39-5

caffeic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

139-85-5

3,4-dihydroxybenzaldehyde

C

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

D

(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%
583-50-6

D-erythrose

A

67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

99-50-3

3,4-Dihydroxybenzoic acid

C

1197-09-7

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

D

55087-82-6

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

E

139-85-5

3,4-dihydroxybenzaldehyde

F

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%
67-56-1

methanol

4-benzenesulfonyloxy-3-hydroxy-benzaldehyde

124-41-4

sodium methylate

A

121-33-5

vanillin

B

139-85-5

3,4-dihydroxybenzaldehyde

128-08-5

N-Bromosuccinimide

120-57-0

piperonal

67-66-3

chloroform

A

60546-62-5

6-bromopiperonylic acid

B

15930-53-7

6-bromo-3,4-methylenedioxybenzaldehyde

C

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
auch unter Zusatz von Dibenzoylperoxid;
866998-51-8

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

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With water
With diluted acids
623-11-0

1-methyl-4-nitrosobenzene

2973-78-6

3-bromo-4-hydroxybenzylaldehyde

A

99-50-3

3,4-Dihydroxybenzoic acid

B

123-08-0

4-hydroxy-benzaldehyde

C

139-85-5

3,4-dihydroxybenzaldehyde

D

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
at 160℃;
at 190℃;
65298-98-8

4-hydroxy-3-(methoxymethoxy)benzaldehyde

139-85-5

3,4-dihydroxybenzaldehyde

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

hexamethylenetetramine

120-80-9

benzene-1,2-diol

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With p-dimethylaminonitrosobenzene
3328-70-9

5-formyl-2-hydroxybenzaldehyde

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
2973-78-6

3-bromo-4-hydroxybenzylaldehyde

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

139-85-5

3,4-dihydroxybenzaldehyde

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

benzyl chloride

139-85-5

3,4-dihydroxybenzaldehyde

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%
18162-48-6

tert-butyldimethylsilyl chloride

139-85-5

3,4-dihydroxybenzaldehyde

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%
112-29-8

1-bromo dodecane

139-85-5

3,4-dihydroxybenzaldehyde

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%
106-95-6

allyl bromide

139-85-5

3,4-dihydroxybenzaldehyde

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%
139-85-5

3,4-dihydroxybenzaldehyde

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.
1029302-64-4

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

139-85-5

3,4-dihydroxybenzaldehyde

1448150-60-4

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

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

dimedone

109-77-3

malononitrile

139-85-5

3,4-dihydroxybenzaldehyde

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%
74-90-8

hydrogen cyanide

139-85-5

3,4-dihydroxybenzaldehyde

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%
141-97-9

ethyl acetoacetate

109-77-3

malononitrile

139-85-5

3,4-dihydroxybenzaldehyde

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%

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

139-85-5

3,4-dihydroxybenzaldehyde

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

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

BARBITURIC ACID

139-85-5

3,4-dihydroxybenzaldehyde

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%
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    Protocatechualdehyde

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    Protocatechualdehyde CAS:139-85-5

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    Chemical Name: Protocatechualdehyde CAS No.: 139-85-5 Molecular Fomula: C7H6O3 Chemical Structure: Molecular weight: 138.12 Appearance: powder Appearance:Slightly Brown Powder Storage:Store in cool and dry place, away from sun light. Pac

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    139-85-5 Protocatechualdehyde

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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,