Conditions | Yield |
---|---|
With carbon dioxide at 100℃; for 24h; | 89% |
2-(2,6-dihydroxyphenyl)acetic acid
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With iodine; dimethyl sulfoxide at 120℃; for 27h; Sealed tube; Green chemistry; | 82% |
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation; | 75% |
Conditions | Yield |
---|---|
With potassium hydroxide under 10501.1 - 26252.6 Torr; for 4h; Reagent/catalyst; | 54.6% |
Stage #1: carbon dioxide; recorcinol With potassium carbonate In ethanol; water at 170℃; under 17251.7 - 18751.9 Torr; for 5h; Stage #2: With sulfuric acid In ethanol; water at 98 - 100℃; for 11h; pH=5.5 - 6; Solvent; Reagent/catalyst; | |
With potassium carbonate; phenol In water at 120℃; for 16h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 20℃; for 1h; UV-irradiation; Green chemistry; | A 7% B 8% |
Conditions | Yield |
---|---|
Isomerisierung ueber das Natrium- oder das Kalium-Salz; |
Conditions | Yield |
---|---|
With aluminium trichloride | |
With aluminium trichloride; benzene |
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With nickel; potassium hydrogencarbonate |
n-butyllithium
diethyl ether
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
anschliessendes Behandeln mit festem CO2; |
sodium methylate
methylammonium carbonate
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 100℃; under 4560 Torr; |
methylammonium carbonate
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium methylate at 100℃; under 4560 Torr; |
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether anschliessend Behandeln mit Kohlendioxid; | |
With carbon dioxide; potassium hydrogencarbonate at 120℃; | |
With salicylic acid decarboxylase from Trichosporon moniliiforme; potassium hydrogencarbonate at 30℃; for 24h; pH=8.5; aq. phosphate buffer; Enzymatic reaction; |
Conditions | Yield |
---|---|
at 27℃; for 24h; Product distribution; Pseudomonas sp. TA-2 cells, phosphate buffer; metabolism, degradation pathway; |
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; |
carbon dioxide
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 120℃; |
carbon dioxide
water
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 93 - 130℃; |
methylammonium carbonate
glycerol
recorcinol
A
4-hydroxysalicylic acid
B
4,6-dihydroxyisophthalic acid
C
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 210℃; |
methylammonium carbonate
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether anschliessend Behandeln mit wss. Salzsaeure; |
aluminium trichloride
2-6-dimethoxybenzoic acid
benzene
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With ammonium carbonate; water at 120 - 130℃; | |
With sodium hydrogencarbonate; glycerol at 135℃; |
Conditions | Yield |
---|---|
With glycerol at 135℃; |
Conditions | Yield |
---|---|
beim Schmelzen; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: Raney nickel; aqueous KHCO3 View Scheme |
potassium hydrogencarbonate
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With Trichosporon moniliiforme WU-0401 salicylic acid decarboxylase at 30℃; for 1h; pH=7; enzymatic Kolbe-Schmitt reaction; aq. phosphate buffer; Enzymatic reaction; regioselective reaction; |
Conditions | Yield |
---|---|
With 2,6-dihydroxybenzoic acid decarboxylase from Rhizobium species; potassium hydrogencarbonate at 30℃; for 24h; pH=8.5; aq. phosphate buffer; Enzymatic reaction; regioselective reaction; |
Conditions | Yield |
---|---|
With 2,6-dihydroxybenzoatedecarboxylase fromRhizobium sp In aq. phosphate buffer at 30℃; for 24h; Kolbe-Schmidt Synthesis; Enzymatic reaction; regioselective reaction; |
carbon dioxide
recorcinol
A
4-hydroxysalicylic acid
B
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium carbonate at 120℃; for 5.7h; Temperature; |
2,6-Dihydroxybenzoic acid
benzyl bromide
benzyl 2,6-dibenzyloxybenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 11h; Heating; | 100% |
With 18-crown-6 ether; potassium carbonate In acetone | |
With 18-crown-6 ether; potassium carbonate In acetone Esterification; Heating; |
2,6-Dihydroxybenzoic acid
2,6-dihydroxybenzoic-3,5-d2 acid
Conditions | Yield |
---|---|
With water-d2; hydrogen chloride for 1h; Inert atmosphere; Reflux; | 99% |
diazomethane
2,6-Dihydroxybenzoic acid
methyl 2,6-dihydroxybenzoate
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 98% |
60% |
2,6-Dihydroxybenzoic acid
acetone
5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
Conditions | Yield |
---|---|
With dmap; thionyl chloride In 1,2-dimethoxyethane Cyclization; | 96% |
With dmap; thionyl chloride In 1,2-dimethoxyethane | 96% |
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 24h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: 2,6-Dihydroxybenzoic acid; benzyl bromide With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 20h; Further stages.; | 94% |
Conditions | Yield |
---|---|
With ammonium hydroxide; silver nitrate In water at 0 - 20℃; for 18.5h; | 89% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide | 77% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 96h; Methylation; | 77% |
With potassium carbonate In N,N-dimethyl-formamide for 24h; Ambient temperature; | |
With ammonia; silver nitrate In water at 0 - 5℃; for 12.5h; |
2,6-Dihydroxybenzoic acid
chloroacetyl chloride
6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid
Conditions | Yield |
---|---|
With aluminum (III) chloride In ethyl acetate; nitrobenzene at 40℃; for 12h; | 89% |
Conditions | Yield |
---|---|
In toluene for 1h; Sealed tube; Heating; | 89% |
2,6-Dihydroxybenzoic acid
di-tert-butylsilyl bis(trifluoromethanesulfonate)
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In acetonitrile at 0 - 22℃; for 16h; Inert atmosphere; | 87% |
2,6-Dihydroxybenzoic acid
2,6-dihydroxy-3,5-dichlorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 20℃; | 85% |
With sulfuryl dichloride | |
With sulfuryl dichloride |
2,6-Dihydroxybenzoic acid
4,6-dimethoxypyrimidin-2-yl methyl sulfone
bispyribac
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate In toluene Reagent/catalyst; Solvent; Reflux; | 85% |
Stage #1: 2,6-Dihydroxybenzoic acid; 4,6-dimethoxypyrimidin-2-yl methyl sulfone With sodium hydride In N,N-dimethyl acetamide; toluene; paraffin oil at 100℃; for 5h; Stage #2: With methanol at 20℃; for 1h; Solvent; Temperature; | 83% |
Conditions | Yield |
---|---|
In water addn. of 2 equiv. of ligand to K2MoO4, filtration, addn. of 2 equiv. ofPPh4Cl (pptn.); filtration, washing (H2O), drying in air; elem. anal.; | 82% |
Conditions | Yield |
---|---|
In ethanol; water | 81% |
2,6-Dihydroxybenzoic acid
6-chloro-4-nitrosoresorcinol
Conditions | Yield |
---|---|
With sulfuric acid In water | 81% |
2,6-Dihydroxybenzoic acid
ethyl bromoacetate
ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 2h; Reflux; | 81% |
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; Reflux; Inert atmosphere; | 80% |
With sulfuric acid for 168h; Heating; | 67% |
With sulfuric acid for 36h; Heating; | 65% |
2,6-Dihydroxybenzoic acid
α-bromoacetophenone
2,6-Dihydroxy-benzoic acid 2-oxo-2-phenyl-ethyl ester
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide | 80% |
2,6-Dihydroxybenzoic acid
acetonitrile
N,N′-dimethyl-N,N′-bis(2-hidroxy-3-formyl-5-bromo-benzyl)ethylenediamine
Conditions | Yield |
---|---|
With triethylamine at 80℃; for 0.5h; | 80% |
2,6-Dihydroxybenzoic acid
2,6-dihydroxy benzohydrazide
Conditions | Yield |
---|---|
Stage #1: 2,6-Dihydroxybenzoic acid With potassium carbonate; dimethyl sulfate In acetone at 55℃; for 24h; Stage #2: With hydrazine hydrate In methanol at 20℃; for 2h; | 80% |
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 24 h / 55 °C 2: hydrazine hydrate / methanol / 2 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With polyphosphoric acid at 200℃; for 4h; | 79% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In diethyl ether; water | 77% |
Conditions | Yield |
---|---|
With phosphorus trichloride In chlorobenzene at 135℃; for 0.333333h; Microwave irradiation; | 76% |
With phosphorus trichloride |
2,6-Dihydroxybenzoic acid
1,1,1,3,3,3-hexamethyl-disilazane
2,6-bis[(trimethylsilyl)oxy]benzoic acid trimethylsilyl ester
Conditions | Yield |
---|---|
With iodine In neat (no solvent) at 20℃; for 16h; Green chemistry; | 76% |
With pyridine |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 5h; Inert atmosphere; | 76% |
With potassium carbonate In acetone at 55℃; for 24h; |
Conditions | Yield |
---|---|
In water Sonication; | 75.4% |
The IUPAC name of this hcemical is 2,6-dihydroxybenzoic acid. With the CAS registry number 303-07-1, it is also named as gamma-Resorcylic acid. The product's categories are Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic Acids. It is off-white crystalline powder which is soluble in alcohol, ether and hot water. Additioanlly, this chemical should be sealed in the container and avoided direct sunshine.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.38; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.671; (11)Molar Refractivity: 36.946 cm3; (12)Molar Volume: 98.823 cm3; (13)Polarizability: 14.647×10-24 cm3; (14)Surface Tension: 84.283 dyne/cm; (15)Enthalpy of Vaporization: 62.008 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Rotatable Bond Count: 1; (18)Tautomer Count: 7; (19)Exact Mass: 154.026609; (20)MonoIsotopic Mass: 154.026609; (21)Topological Polar Surface Area: 77.8; (22)Heavy Atom Count: 11; (23)Complexity: 147.
The preparation method of 2,6-Dihydroxybenzoic acid: Firstly, dissolving resorcinol in ethanol and adding anhydrous potassium carbonate in this solution. Secondly, heating to 140 °C and access to carbon dioxide to react 4h. After reaction, we can get the mixture on of 2,6-dihydroxybenzoic acid and 2,4-dihydroxybenzoic acid mixture. Through the separation and filtration, we can get the product of 2,6-Dihydroxybenzoic acid.
Uses of 2,6-Dihydroxybenzoic acid: It is mainly used as intermediate of pesticide, pharmaceutical and herbicide. It also can react with methanol to get 2,6-dihydroxy-benzoic acid methyl ester. This reaction needs reagent hydrogen chloride.
When you are using this chemical, please be cautious about it as the following:
It is trritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:c1cc(c(c(c1)O)C(=O)O)O
2. InChI:InChI=1/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
3. InChIKey:AKEUNCKRJATALU-UHFFFAOYAG
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 600mg/kg (600mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 196, Pg. 478, 1976. | |
mouse | LD50 | intravenous | > 600mg/kg (600mg/kg) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1969. |
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