Name: 2,4-Dihydroxybenzoic acid
SKU: 89-86-1

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Basic Information

Molecular Structure:
CAS No.:	89-86-1
Name:	2,4-Dihydroxybenzoic acid

Formula:	C₇H₆O₄
Molecular Weight:	154.122
Synonyms:	beta-Resorcylicacid (8CI);4-Carboxyresorcinol;4-Hydroxysalicylicacid;Coupler 320;NSC 13564;NSC 4740;p-Hydroxysalicylic acid;beta-Resorcylic acid;
EINECS:	201-946-9
Density:	1.56 g/cm³
Melting Point:	225-227 °C
Boiling Point:	414.833 °C at 760 mmHg
Flash Point:	218.835 °C
Solubility:	soluble in ethanol, diethyl ether and hot water
Appearance:	cream to slightly beige or pink crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36-37/39
PSA:	77.76000
LogP:	0.79600

Synthetic route

: 108-46-3
recorcinol

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With hydrogenchloride; CO2; potassium carbonate In water	96.7%
With potassium dicarbonate; water
With sodium hydrogencarbonate anschliessendes Einleiten von Kohlendioxid;

: 2517-43-3
3-methoxy butanol

: 108-46-3
recorcinol

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; CO2 In water	95.4%
With CO2; potassium carbonate In water	87.4%

: 95-01-2
2,4-Dihydroxybenzaldehyde

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With sodium chlorite; sodium methylate In dimethyl sulfoxide	95%
With tert.-butylhydroperoxide; copper(ll) bromide In water; acetonitrile at 20℃; for 9h; Inert atmosphere; chemoselective reaction;	91%
With dihydrogen peroxide; silver nitrate In acetonitrile at 50℃; for 1h; chemoselective reaction;	90%
With potassium carbonate beim Schmelzen;

: 69-72-7
salicylic acid

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 20℃; for 1h; UV-irradiation; Green chemistry; regioselective reaction;	92%

: 33617-59-3
1,3-dihydroxy-4-dihydroxymethyl benzene

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(ll) bromide In water; dimethyl sulfoxide for 22h; Inert atmosphere; Reflux; chemoselective reaction;	89%

: 89-84-9
2',4'-dihydroxy-4-acetophenone

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With N-bromophthalimide; mercury(II) diacetate In chloroform at 20℃; for 2h;	86%
Multi-step reaction with 2 steps 1: iodine 2: aq.-ethanolic NaOH-solution View Scheme
With dihydrogen peroxide In water at 22 - 25℃; for 11688h;

: 107-98-2
1-methoxy-2-propanol

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With hydrogenchloride; CO2; potassium carbonate In water	85%

: 124-38-9
carbon dioxide

: 108-46-3
recorcinol

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 30℃; under 15001.5 Torr; for 28h; Solvent; Reagent/catalyst; Kolbe-Schmidt Synthesis; Autoclave;	84%
With water; sodium hydrogencarbonate at 100℃; for 3h; Kolbe-Schmidt Synthesis;	64%
With potassium hydrogencarbonate In water for 4h; Reflux;

: 614-82-4
(2,4-dihydroxyphenyl)acetic acid

: 89-86-1
4-hydroxysalicylic acid

Conditions

Conditions	Yield
With iodine; dimethyl sulfoxide at 120℃; for 28h; Sealed tube; Green chemistry;	83%

: 108-24-7
acetic anhydride

: 89475-40-1
2,4,4'-Triacetoxy-3'-methoxy-chalkon

A: 89-86-1
4-hydroxysalicylic acid

B: 121-34-6
3-methoxy-4-hydroxybenzoic acid

Conditions

Conditions	Yield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetone, water, 20 min : decomposition reaction;	A 54% B 73%

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2,4-Dihydroxybenzoic acid, with the CAS registry number 89-86-1, is also known as beta-Resorcylic acid. It belongs to the product categories of Intermediates of Dyes and Pigments; Fine Chemical & Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid Derivative; Organic acids; Building Blocks; C7; Carbonyl Compounds; Carboxylic Acids; Chemical Synthesis; Organic Building Blocks. Its EINECS number is 201-946-9. This chemical's molecular formula is C₇H₆O₄ and molecular weight is 154.12. What's more, its systematic name is 2,4-Dihydroxybenzoic acid. Its classification code is Reproductive Effect. This chemical should be sealed and stored in a cool and dry place. It is used as an intermediate for dyestuffs and drugs. is a dihydroxybenzoic acid. As a resorcyclic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid. It is a degradation product of cyanidin glycosides from tart cherries in cell cultures. It is also a metabolite found in human plasma after cranberry juice consumption.

Physical properties of 2,4-Dihydroxybenzoic acid are: (1)ACD/LogP: 1.765; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.08; (4)ACD/LogD (pH 7.4): -1.39; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 77.76 Å²; (13)Index of Refraction: 1.671; (14)Molar Refractivity: 36.946 cm³; (15)Molar Volume: 98.823 cm³; (16)Polarizability: 14.647×10^-24cm³; (17)Surface Tension: 84.3 dyne/cm; (18)Density: 1.56 g/cm³; (19)Flash Point: 218.835 °C; (20)Enthalpy of Vaporization: 70.412 kJ/mol; (21)Boiling Point: 414.833 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,4-dihydroxy-benzaldehyde. This reaction will need reagents NaClO₂, CH₃ONa and solvent dimethylsulfoxide. The yield is about 95%.

2,4-Dihydroxybenzoic acid can be prepared by 2,4-dihydroxy-benzaldehyde

Uses of 2,4-Dihydroxybenzoic acid: it can be used to produce 2,4-dihydroxy-benzoic acid methyl ester by heating. It will need reagent H₂SO₄ with the reaction time of 72 hours. The yield is about 100%.

2,4-Dihydroxybenzoic acid can be used to produce 2,4-dihydroxy-benzoic acid methyl ester by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1O)O)C(=O)O
(2)Std. InChI: InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11)
(3)Std. InChIKey: UIAFKZKHHVMJGS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 800mg/kg (800mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 196, Pg. 478, 1976.

89-86-1

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Consensus Reports

Specification