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303-07-1

Basic Information
CAS No.: 303-07-1
Name: 2,6-Dihydroxybenzoic acid
Article Data: 36
Cas Database
Molecular Structure:
Molecular Structure of 303-07-1 (2,6-Dihydroxybenzoic acid)
Formula: C7H6O4
Molecular Weight: 154.122
Synonyms: 6-Hydroxysalicylic acid;2-Carboxyresorcinol;gamma-Resorcylic acid;Benzoic acid, 2,6-dihydroxy-;4-10-00-01456 (Beilstein Handbook Reference);2,6-Resorcylic acid;gamma-Resorcylic acid (8CI);2,6-Dihydroxy benzoic acid;2,6-dihydroxybenzoic acid ;2,6-resorcylic acid; gamma-resorcylic acid;
EINECS: 206-134-8
Density: 1.56 g/cm3
Melting Point: 154-155 °C
Boiling Point: 343.66 °C at 760 mmHg
Flash Point: 175.839 °C
Solubility: Soluble in alcohol, ether and hot water
Appearance: Off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 77.76000
LogP: 0.79600
Synthetic route
56-81-5

glycerol

108-46-3

recorcinol

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With carbon dioxide at 100℃; for 24h;89%
64700-73-8

2-(2,6-dihydroxyphenyl)acetic acid

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 120℃; for 27h; Sealed tube; Green chemistry;82%

1-(2,6-dihydroxyphenyl)butane-1,3-dione

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;75%
124-38-9

carbon dioxide

108-46-3

recorcinol

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
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;
69-72-7

salicylic acid

A

89-86-1

4-hydroxysalicylic acid

B

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 1h; UV-irradiation; Green chemistry;A 7%
B 8%
699-83-2

2,6-dihydroxylacetophenone

303-07-1

2,6-Dihydroxybenzoic acid

89-86-1

4-hydroxysalicylic acid

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
Isomerisierung ueber das Natrium- oder das Kalium-Salz;
1466-76-8

2-6-dimethoxybenzoic acid

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With aluminium trichloride
With aluminium trichloride; benzene

2,6-dihydroxy-4-(toluene-4-sulfonyloxy)-benzoic acid

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
With nickel; potassium hydrogencarbonate
109-72-8, 29786-93-4

n-butyllithium

60-29-7

diethyl ether

108-46-3

recorcinol

A

89-86-1

4-hydroxysalicylic acid

B

303-07-1

2,6-Dihydroxybenzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit festem CO2;
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Specification

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.