2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With methanol; iodine at 20℃; for 48h; | 96% |
A
2,5-dihydroxybenzoic acid.
B
3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin
Conditions | Yield |
---|---|
In trifluoroacetic acid for 17h; Heating; | A 25% B 31% C 8.5% |
benzoic acid
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
C
3-Carboxyphenol
D
salicylic acid
E
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; pH 6.8 buffer; | A 9% B 5% C 14% D 4% E 9% |
benzoic acid
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
C
3-Carboxyphenol
D
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Further byproducts given; | A 9% B 5% C 14% D 9% |
Conditions | Yield |
---|---|
With potassium hydroxide durch Schmelzen; |
Conditions | Yield |
---|---|
With permanganate(VII) ion; magnesium sulfate at 85℃; folgende Verseifung mit Salzsaeure; |
Conditions | Yield |
---|---|
Diazotization.Kochen der erhaltenen Diazoverbindung mit Wasser; |
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With sodium hydroxide; copper | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With sodium hydroxide; water |
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With sulfuric acid |
methylammonium carbonate
hydroquinone
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With potassium carbonate at 140 - 210℃; |
Conditions | Yield |
---|---|
With potassium sulfite; water; potassium hydrogencarbonate at 130℃; | |
With potassium hydrogencarbonate; glycerol at 180℃; | |
Multi-step reaction with 2 steps 1: NaOH-solution 2: potassium hydroxide / durch Schmelzen View Scheme | |
With tetrachloromethane; sodium hydroxide; copper |
Conditions | Yield |
---|---|
With phosphate buffer; oxygen; rose bengal Rate constant; Mechanism; Irradiation; other singlet oxygen generating systems; effect of inhibitors; | |
With potassium peroxomonosulphate Kochen des Reaktionsproduktes mit verd. Salzsaeure; | |
With dipotassium peroxodisulfate |
salicylic acid
A
2,5-dihydroxybenzoic acid.
B
2,3,5-trihydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; ammonium peroxydisulfate |
carbon dioxide
p-Isopropoxyphenyl methyl ether
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
Multistep reaction; |
2,5-dihydroxybenzoic acid benzyl ester
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Yield given; |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; dihydrogen peroxide; methylene blue at 25℃; for 4h; Product distribution; Mechanism; Irradiation; other salicylic derivatives, hydroxylation; | |
With oxygen; potassium oxalate; iron(III) chloride In water at 25℃; Product distribution; Irradiation; role of hydrogen peroxide in dyoxygen induced hydroxylation of title compound; photochemicall and thermal (pH 7.1) hydroxylation; | |
With dihydrogen peroxide In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time, HClO4 or K2CO3 presence; |
Conditions | Yield |
---|---|
With Fe(III)(sal)3(3-); dihydrogen peroxide In water at 25℃; for 1h; Product distribution; Thermodynamic data; Irradiation; other times; presence of O2; |
Conditions | Yield |
---|---|
With β-glucosidase for 168h; Ambient temperature; enzymatic hydrolysis; |
salicylate
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time; |
salicylic acid
A
4-hydroxysalicylic acid
B
2,3-Dihydroxybenzoic acid
C
2,5-dihydroxybenzoic acid.
D
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate In water at 37℃; for 0.0833333h; hydroxylation; Further byproducts given. Title compound not separated from byproducts; |
2,5-dihydroxybenzoic acid 2-O-β-4C1-glucopyranoside
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 3h; Hydrolysis; |
Conditions | Yield |
---|---|
In water Oxidation; Formation of xenobiotics; simulated solar irradiation; |
hydrogenchloride
4,7-dihydroxyisoindole-1,3-dione
2,5-dihydroxybenzoic acid.
6-hydroxy-2,3-dimethyl-chromen-4-one
2,5-dihydroxybenzoic acid.
gentisin
A
3,5-dihydroxyphenol
B
2,5-dihydroxybenzoic acid.
C
acetic acid
Conditions | Yield |
---|---|
Beim Schmelzen; |
1,2,3,4-tetrahydroisoquinoline
sulfuric acid
A
2,5-dihydroxybenzoic acid.
B
oxalic acid
C
propionic acid
D
maleic acid
Conditions | Yield |
---|---|
Electrolysis; |
Conditions | Yield |
---|---|
for 0.5h; | 100% |
In tetrahydrofuran Product distribution / selectivity; |
Conditions | Yield |
---|---|
In toluene for 0.75h; | 100% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; | 99% |
Stage #1: 2,5-dihydroxybenzoic acid. With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h; Stage #2: methyl iodide In acetone at 20℃; for 4h; | 92% |
2,5-dihydroxybenzoic acid.
allyl bromide
allyl 2,5-bis(allyloxy)benzoate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; | 99% |
Stage #1: 2,5-dihydroxybenzoic acid. With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.05h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 48h; | 78% |
2,5-dihydroxybenzoic acid.
pomalidomide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Solvent; Temperature; | 99% |
2,5-dihydroxybenzoic acid.
boron trifluoride diethyl etherate
ethyl 2,5-dihydroxybenzoate
Conditions | Yield |
---|---|
at 120℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium hydrogencarbonate In N,N-dimethyl acetamide at 70℃; for 24h; Inert atmosphere; | 98.4% |
With potassium hydrogencarbonate In N,N-dimethyl acetamide at 65℃; for 24h; Inert atmosphere; | 98.4% |
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere; | 78% |
2,5-dihydroxybenzoic acid.
benzyl chloride
2,5-dihydroxybenzoic acid benzyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 70℃; for 12h; | 98% |
2,5-dihydroxybenzoic acid.
benzyl bromide
2,5-dihydroxybenzoic acid benzyl ester
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl acetamide at 65℃; for 24h; Inert atmosphere; | 98% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h; | 93% |
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; | 91% |
Conditions | Yield |
---|---|
With sulfuric acid for 48h; Reflux; | 97% |
With sulfuric acid at 25℃; for 12h; Reflux; Inert atmosphere; | 97% |
With 95percent H2SO4 Heating; | 96% |
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With Amberlite IRA-410 10 (OH(1-)form) In water | 97% |
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
In water; acetone at 20℃; for 1h; Product distribution / selectivity; | 96.5% |
In water; acetone at 20℃; Product distribution / selectivity; | 96.5% |
In acetone at 20℃; for 1h; Product distribution / selectivity; | 77.1% |
2,5-dihydroxybenzoic acid.
allyl bromide
allyl 5-allyloxy-2-hydroxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 96% |
Conditions | Yield |
---|---|
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Cooling with ice; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Cooling with ice; | 96% |
With potassium carbonate |
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 3h; Heating; | 96% |
With phosphorus trichloride In chlorobenzene at 135℃; for 0.333333h; Microwave irradiation; | 58% |
2,5-dihydroxybenzoic acid.
bosentan
N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide gentisic acid cocrystal
Conditions | Yield |
---|---|
In n-heptane; acetone at 55℃; for 2.33333h; Concentration; Solvent; Temperature; Time; Sonication; | 96% |
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With air In acetonitrile at 10 - 35℃; for 120h; Sealed tube; | 96% |
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
In ethanol at 48℃; | 95.62% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃; | 95% |
2,5-dihydroxybenzoic acid.
dimethyl sulfate
methyl 5-methoxy-2-hydroxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; for 30h; | 94% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 70℃; | 94% |
Conditions | Yield |
---|---|
With sulfuric acid for 144h; Heating; | 93% |
With thionyl chloride at 0℃; Reflux; Inert atmosphere; | 60% |
With sulfuric acid |
2,5-dihydroxybenzoic acid.
benzyl chloride
benzyl 2,5-bis(benzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h; | 93% |
With potassium carbonate In butanone for 16h; Heating; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 9.5h; Heating; | 93% |
With toluene-4-sulfonic acid In toluene at 120℃; for 8h; | 81.1% |
With sulfuric acid Fischer-Speier Esterification; |
Conditions | Yield |
---|---|
With sodium acetate In water; acetonitrile Electrochemical reaction; | 93% |
2,5-dihydroxybenzoic acid.
allyl bromide
5-allyloxy-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; | 92.9% |
Stage #1: 2,5-dihydroxybenzoic acid. With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide pH=3; | 75% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 40℃; for 0.333333h; | 92% |
2,5-dihydroxybenzoic acid.
S-amlodipine gentisate
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate With sodium hydroxide In dichloromethane; water for 0.5h; Stage #2: 2,5-dihydroxybenzoic acid. In dichloromethane; acetone at 20℃; for 2h; | 92% |
2,5-dihydroxybenzoic acid.
S-amlodipine gentisate
Conditions | Yield |
---|---|
Stage #1: (S)-(-)-amlodipine-hemi-dibenzoyl-D-tartrate With sodium hydroxide In dichloromethane; water for 0.5h; Stage #2: 2,5-dihydroxybenzoic acid. In dichloromethane; acetone at 20℃; for 2h; | 92% |
The IUPAC name of Gentisic acid is 2,5-dihydroxybenzoic acid. With the CAS registry number 490-79-9, it is also named as Acido 2,5-diidrossibenzoico. The product's categories are Organic Acids; Analytical Chemistry; Mass Spectrometry; Matrix Materials (MALDI-TOF-MS). Besides, it is white to light beige crystalline powder. In addition, its molecular formula is C7H6O4 and molecular weight is 154.12.
The other characteristics of this product can be summarized as: (1)EINECS: 207-718-5; (2)ACD/LogP: 1.56; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -1.46; (5)ACD/LogD (pH 7.4): -1.59; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 4; (11)#H bond donors: 3; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.67; (14)Molar Refractivity: 36.94 cm3; (15)Molar Volume: 98.8 cm3; (16)Surface Tension: 84.2 dyne/cm; (17)Density: 1.559 g/cm3; (18)Flash Point: 214 °C; (19)Melting point: 204-207 °C; (20)Enthalpy of Vaporization: 69.45 kJ/mol; (21)Boiling Point: 406.9 °C at 760 mmHg; (22)Vapour Pressure: 2.38E-07 mmHg at 25 °C.
Preparation of Gentisic acid: this chemical can be prepared by carboxylation of Hydroquinone:
C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2
Uses of Gentisic acid: this chemical can be used as an antioxidant excipient in some pharmaceutical preparations. In the laboratory, it is used in matrix-assisted laser MALDI mass spectrometry as a sample matrix. Furthermore, it can react with Methanol to get 2,5-Dihydroxy-benzoic acid methyl ester.
This reaction needs 95 percent H2SO4 by heating. The yield is 96 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also harmful if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O)c1cc(O)ccc1O
(2)InChI: InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
(3)InChIKey: WXTMDXOMEHJXQO-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
(5)Std. InChIKey: WXTMDXOMEHJXQO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 374mg/kg (374mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 254, 1953. |
mouse | LD50 | oral | 4500mg/kg (4500mg/kg) | British Journal of Pharmacology and Chemotherapy. Vol. 8, Pg. 30, 1953. | |
rat | LD50 | intraperitoneal | 3gm/kg (3000mg/kg) | Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973. |
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