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3,4-Dihydroxybenzoic acid

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Name

3,4-Dihydroxybenzoic acid

EINECS 202-760-0
CAS No. 99-50-3 Density 1.559 g/cm3
PSA 77.76000 LogP 0.79600
Solubility Soluble in hot alcohol and ether. Slightly soluble in water. Melting Point 197-200 °C (dec.)(lit.)
Formula C7H6O4 Boiling Point 410.7 °C at 760 mmHg
Molecular Weight 154.12 . Flash Point 216.3 °C
Transport Information Appearance white to light yellow crystal powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 99-50-3 (3,4-Dihydroxybenzoic acid) Hazard Symbols IrritantXi
Synonyms

4-Carboxy-1,2-dihydroxybenzene;Protocatehuic acid;1/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11;4-10-00-01459 (Beilstein Handbook Reference);Benzoic acid, 3,4-dihydroxy- (9CI);Benzoic acid,3,4-dihydroxy-;3.4-Dihydroxy Benzoic Acid;Protocatechuate;3,4-Dihydroxy Benzoic Acid;Benzoic acid, 3,4-dihydroxy-;3,4-dihydroxybenzoic acid;protocatechuic acid;3,4-Dihydroxybenzoic Acid 98%;

 

3,4-Dihydroxybenzoic acid Synthetic route

121-34-6

3-methoxy-4-hydroxybenzoic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;100%
With 1,4-dithio-D,L-threitol; phosphite dehydrogenase; phosphite ion; iron(II) sulfate; NADH In dimethyl sulfoxide at 30℃; for 7h; pH=7.5; Catalytic behavior; Reagent/catalyst; Solvent; Enzymatic reaction;77%
121-33-5

vanillin

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 260℃; for 0.75h;94%
With potassium carbonate durch Schmelzen;
With potassium hydroxide durch Schmelzen;
With potassium hydroxide at 250℃;
6702-50-7

3-hydroxy-4-methoxybenzoate

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;89%
874-61-3

4-oxocyclohexanecarboxylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;84%
3943-74-6

4-hydroxy-3-methoxybenzoic acid methyl ester

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; ethyl acetate; diisopropyl-carbodiimide In acetonitrile at 80℃; for 5h; Temperature;A 14%
B 72%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h; Temperature; Overall yield = 89 %; Overall yield = 0.684 g;A 64%
B 31%
619-12-5

4-formyl-3-hydroxybenzoic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 35℃; for 12h; Dakin Phenol Oxidation;71%
108-24-7

acetic anhydride

89475-36-5

3',4'-dihydroxy-7-dimethoxyflavylium chloride

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2237-36-7

4-methoxysalicylic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;A 70%
B 67%
6702-50-7

3-hydroxy-4-methoxybenzoate

A

99-50-3

3,4-Dihydroxybenzoic acid

B

2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 40℃; for 18h;A 64%
B 31%
16205-98-4

3-oxo-cyclohexanecarboxylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h; regioselective reaction;63%
2922-42-1

(-)-3-dehydroshikimic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With copper diacetate In water; acetic acid at 40℃; for 36h; Oxidation; aromatization;A 0.7%
B 62%
With copper diacetate; oxygen; zinc(II) oxide In acetic acid at 50℃; under 760.051 Torr; for 14h; Kinetics; Product distribution; Further Variations:; Reagents; Oxidation; aromatization;
139-85-5

3,4-dihydroxybenzaldehyde

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium bromate; hydrogenchloride; potassium bromide In water for 12h; Time;55%
With potassium carbonate durch Schmelzen;
With potassium hydroxide at 150 - 190℃; Ausschluss von Sauerstoff;
67-56-1

methanol

10534-44-8

3-dehydroquinic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

84806-48-4

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate

C

57764-14-4

methyl 3-dehydroquinate

Conditions
ConditionsYield
With Amberlite IR 120 for 1.5h; Heating;A 30%
B 20%
C 50%

cyanidin 3-O-glucopyranoside chloride

A

99-50-3

3,4-Dihydroxybenzoic acid

glucopyranosyl 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetate

C14H16O10

Conditions
ConditionsYield
With 2,2'-azobis-(2,4-dimethylvaleronitrile) In water; acetonitrile at 60℃; for 6h;A 34%
B 13.6%
C 15%
117-39-5

quercetol

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 18h;17%
With potassium carbonate beim Schmelzen;
With potassium carbonate
With potassium hydroxide
With potassium hydroxide Heating;
2922-42-1

(-)-3-dehydroshikimic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

99-14-9

tricarallylic acid

C

149-91-7

3,4,5-trihydroxybenzoic acid

D

184105-29-1

dihydrogallic acid

E

87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With air; Na1.5H1.5PO4 at 40℃; for 50h; Rate constant; Mechanism; other oxidant, var. time;A 12 % Spectr.
B 14 % Spectr.
C 13%
D n/a
E 3 % Spectr.
99-96-7

4-hydroxy-benzoic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With peroxygenase; dihydrogen peroxide In acetonitrile at 20℃; for 0.5h; pH=5; pH-value; Enzymatic reaction;12.4%
With Aspergillus carbonarius peroxygenase gene; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetonitrile at 20℃; for 0.25h; pH=6; Catalytic behavior; Enzymatic reaction;1%
With potassium peroxomonosulphate Kochen des Reaktionsproduktes mit verd. Salzsaeure;
Multi-step reaction with 2 steps
1: bromine
2: concentrated KOH-solution
View Scheme
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%

cyanidin-3-O-glucoside

A

99-50-3

3,4-Dihydroxybenzoic acid

B

C21H22O13

C

jaboticabin acid (2-O-(3,4-dihydroxybenzoyl)-2,4,6-dihydroxyphenyl)acetic acid

Conditions
ConditionsYield
With water; dihydrogen peroxide In acetonitrile at 40℃; for 8h; Mechanism; Reagent/catalyst; Solvent; Time;A 9%
B n/a
C n/a
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%
120-57-0

piperonal

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With tetrachloromethane; chlorine Einwirkung im Sonnenlicht und Verseifen des entstandenen Chlorids mit Wasser;
79-37-8

oxalyl dichloride

91-16-7

1,2-dimethoxybenzene

99-50-3

3,4-Dihydroxybenzoic acid

97-53-0

4-allylguaiacol

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
Multi-step reaction with 3 steps
1: KOH; water
2: K2cr2O7; glacial acetic acid / 100 °C
3: hydriodic acid / 120 - 130 °C / im geschlossenen Rohr
View Scheme
1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
94-53-1

Piperonylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride at 170℃; im geschlossenen Rohr;
With water at 210℃; im geschlossenen Rohr;
With aluminium trichloride; chlorobenzene
861605-32-5

2-oxo-benzo[1,3]dioxole-5-carboxylic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With water
With salt solution
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℃;
10425-09-9

(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone

A

108-73-6

3,5-dihydroxyphenol

B

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With sulfuric acid at 120℃;
With potassium hydroxide
10425-09-9

(2,4‐dihydroxyphenyl)(3,4,5‐trihydroxyphenyl)methanone

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide
With sulfuric acid at 120℃;
With hydrogenchloride at 120℃;
6331-61-9

2-methoxy-4-(2-propenyl)phenoxyacetic acid

99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
bei der Kalischmelze;
2539-53-9

4-ethoxy-3-hydroxybenzaldehyde

3535-30-6

4-ethoxy-3-methoxybenzoic acid

A

99-50-3

3,4-Dihydroxybenzoic acid

B

90536-50-8

4-ethoxy-3-hydroxy-benzoic acid

Conditions
ConditionsYield
With hydrogen bromide Reaktion ueber mehrere Stufen;
67-56-1

methanol

99-50-3

3,4-Dihydroxybenzoic acid

2150-43-8

3,4-dihydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride Heating;100%
With sulfuric acid for 8h; Reflux;100%
With sulfuric acid under 760.051 Torr; Reflux;100%
99-50-3

3,4-Dihydroxybenzoic acid

931-53-3

Cyclohexyl isocyanide

2393-23-9

4-methoxy-benzylamine

87188-50-9

para-tert-butoxycarbonyloxybenzaldehyde

C34H40N2O8

Conditions
ConditionsYield
Stage #1: 4-methoxy-benzylamine; para-tert-butoxycarbonyloxybenzaldehyde In ethanol; 2,2,2-trifluoroethanol for 4h; Inert atmosphere;
Stage #2: 3,4-Dihydroxybenzoic acid; Cyclohexyl isocyanide In ethanol; 2,2,2-trifluoroethanol for 48h; Inert atmosphere;
100%
99-50-3

3,4-Dihydroxybenzoic acid

64-17-5

ethanol

3943-89-3

Ethyl protocatechuate

Conditions
ConditionsYield
With sulfuric acid Heating;99%
With sulfuric acid at 50℃; for 3h;98%
With sulfuric acid98%
99-50-3

3,4-Dihydroxybenzoic acid

5,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

7,10-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;99%
99-50-3

3,4-Dihydroxybenzoic acid

100-44-7

benzyl chloride

882427-72-7

3,4-(bisbenzyloxy)benzoic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;98%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;98%
With sodium carbonate In N,N-dimethyl-formamide for 48h; Reflux;85%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 85℃; for 12h; Inert atmosphere;
99-50-3

3,4-Dihydroxybenzoic acid

18162-48-6

tert-butyldimethylsilyl chloride

154083-18-8

3,4‐bis(tert‐butyldimethylsilyloxy)benzoic acid

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;98%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;76.7%
With 1H-imidazole In N,N-dimethyl-formamide for 66h; Inert atmosphere;75%
99-50-3

3,4-Dihydroxybenzoic acid

6,8-difluoro-2,3,4,9-tetrahydro-1H-carbazole

7,9-difluoro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
2805-84-7

6-(trifluoromethyl)-2,3,4,9,-tetrahydro-1H-carbazole

99-50-3

3,4-Dihydroxybenzoic acid

C20H16F3NO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
99-50-3

3,4-Dihydroxybenzoic acid

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

9-methyl-13-tosyl-6H-5a,10b-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;96%
99-50-3

3,4-Dihydroxybenzoic acid

140-28-3

N,N'-Dibenzylethylenediamine

1418195-30-8

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction;95.5%
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;
99-50-3

3,4-Dihydroxybenzoic acid

35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

91000-69-0

Fmoc-L-Arg-OH

protocatechuic-RA-NH2

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one for 3h;
Stage #2: With piperidine In 1-methyl-pyrrolidin-2-one
Stage #3: 3,4-Dihydroxybenzoic acid; Fmoc-L-Arg-OH Further stages;
95.215%
99-50-3

3,4-Dihydroxybenzoic acid

108-24-7

acetic anhydride

58534-64-8

3,4-Diacetoxy-benzoesaeure

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;95%
With sulfuric acid at 70℃;86.5%
for 2h; Heating;84%
99-50-3

3,4-Dihydroxybenzoic acid

112-72-1

1-Tetradecanol

tetradecanyl 3,4-dihydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;95%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;36%
With dicyclohexyl-carbodiimide In tetrahydrofuran
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;
99-50-3

3,4-Dihydroxybenzoic acid

75-65-0

tert-butyl alcohol

760947-24-8

3,4-dihydroxy-benzoic acid tert-butyl ester

Conditions
ConditionsYield
With dmap at 20℃; for 72h;95%
99-50-3

3,4-Dihydroxybenzoic acid

101349-10-4

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

C19H15Cl2NO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
99-50-3

3,4-Dihydroxybenzoic acid

53475-34-6

8-chloro-2,3,4,9-tetrahydro-1H-carbazole

C19H16ClNO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
99-50-3

3,4-Dihydroxybenzoic acid

8‐methyl‐2‐tosyl‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

C26H24N2O6S

Conditions
ConditionsYield
With methanesulfonic acid; di-tert-butyl peroxide; iron phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
99-50-3

3,4-Dihydroxybenzoic acid

89424-03-3

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate

C21H20N2O6

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.0833333h; Cooling with ice;95%
99-50-3

3,4-Dihydroxybenzoic acid

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

C24H20N2O6S

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In acetonitrile for 0.25h; Cooling with ice;95%
99-50-3

3,4-Dihydroxybenzoic acid

101349-10-4

6,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole

7,9-dichloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
99-50-3

3,4-Dihydroxybenzoic acid

53475-34-6

8-chloro-2,3,4,9-tetrahydro-1H-carbazole

7-chloro-6H-5a,10b-butanobenzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
99-50-3

3,4-Dihydroxybenzoic acid

2‐(phenylsulfonyl)‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

14-(phenylsulfonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.25h;95%
99-50-3

3,4-Dihydroxybenzoic acid

89424-03-3

ethyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate

14-(ethoxycarbonyl)-6H-10b,5a-(ethanoiminomethano)benzo[5,6][1,4]dioxino[2,3-b]indole-2-carboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h;95%
99-50-3

3,4-Dihydroxybenzoic acid

112-53-8

1-dodecyl alcohol

3,4-dihydroxybenzoic acid dodecyl ester

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;94%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 20h;81%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;33%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;
With sulfuric acid Fischer-Speier Esterification;
99-50-3

3,4-Dihydroxybenzoic acid

100-39-0

benzyl bromide

882427-72-7

3,4-(bisbenzyloxy)benzoic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere;94%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Inert atmosphere;92%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;91%
99-50-3

3,4-Dihydroxybenzoic acid

359-13-7

difluoroethanol

C9H8F2O4

Conditions
ConditionsYield
With thionyl chloride Inert atmosphere; Reflux;94%
99-50-3

3,4-Dihydroxybenzoic acid

2373-51-5

chloro-methylsulfanyl-methane

C9H10O4S

Conditions
ConditionsYield
With triethylamine In acetonitrile Reflux;93.4%
99-50-3

3,4-Dihydroxybenzoic acid

71-36-3

butan-1-ol

37622-53-0

protocatechuic acid n-butyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;93%
With sulfuric acid In tetrahydrofuran at 45 - 65℃; for 120 - 240h; Darkness; Molecular sieve;82%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;64%

3,4-Dihydroxybenzoic acid Chemical Properties

Molecular Formula: C7H6O4
Molecular Weight: 154.12 g/mol 
EINECS: 202-760-0 
Index of Refraction: 1.67
Density: 1.559 g/cm3
Flash Point: 216.3 °C
Enthalpy of Vaporization: 69.92 kJ/mol
Boiling Point: 410.7 °C at 760 mmHg
Vapour Pressure: 1.75E-07 mmHg at 25 °C
Melting point: 197-200 °C (dec.)(lit.)
Sensitive: Air Sensitive
Appearance: White to light yellow crystal powder
Structure of 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3):
                       
IUPAC Name: 3,4-Dihydroxybenzoic acid
Product Category of 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3): Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic Acid Derivative;Organic acids;API

3,4-Dihydroxybenzoic acid Toxicity Data With Reference

1.    

dni-hmn:lyms 1 mmol/L

    BCPCA6    Biochemical Pharmacology. 29 (1980),1275.
2.    

msc-mus:lyms 300 mg/L

    EMMUEG    Environmental and Molecular Mutagenesis. 11 (1988),523.
3.    

cyt-ham:ovr 3 g/L

    CALEDQ    Cancer Letters (Shannon, Ireland). 14 (1981),251.
4.    

ipr-mus LD50:>800 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 196 (1976),478.

3,4-Dihydroxybenzoic acid Safety Profile

Moderately toxic by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.

3,4-Dihydroxybenzoic acid Specification

 3,4-Dihydroxybenzoic acid , its cas register number is 99-50-3. It also can be called Protocatechuic acid . 3,4-Dihydroxybenzoic acid (CAS NO.99-50-3) has mixed effects on normal and cancer cells in in vitro and in vivo studies. It has been reported to induce apoptosis of human leukemia cells, as well as malignant HSG1 cells taken from human oral cavities,but it was found to have mixed effects on TPA-induced mouse skin tumours.
 

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