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99-96-7

Basic Information
CAS No.: 99-96-7
Name: 4-Hydroxybenzoic acid
Article Data: 652
Cas Database
Molecular Structure:
Molecular Structure of 99-96-7 (4-Hydroxybenzoic acid)
Formula: C7H6O3
Molecular Weight: 138.123
Synonyms: p-Oxybenzoesaure [German];Benzoic acid, p-hydroxy-;Benzoic acid, p-hydroxy;4-Carboxyphenol;Benzoic acid, 4-hydroxy-, monosodium salt;4-Hydroxybenzoate;Hydroxybenzenecarboxylic acid;4-Hydroxybenzoesaeure;Benzoic acid, 4-hydroxy-;Benzoic acid, 4-hydroxy;Acido p-idrossibenzoico [Italian];Potassium 4-hydroxybenzoate;Sodium 4-hydroxybenzoate;Hydroxybenzoic acid;p-salicylic acid;Kyselina 4-hydroxybenzoova [Czech];P-Hydroxybenzoic acid (PHBA);4-Hydroxy Benzoic Acid;p-hydroxybenzoic Acid;4-hydroxybenzoic acid;4-hydroxybenzenecarboxylic acid;Para Hydroxy Benzoic Acid[99-96-7];p-Hydroxy Benzoic Acid;
EINECS: 202-804-9
Density: 1.46 g/cm3
Melting Point: 213-217 °C(lit.)
Boiling Point: 336.2 °C at 760 mmHg
Flash Point: 171.3 °C
Solubility: Water solubility: 5 g/L (20 °C)
Appearance: white to beige crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36-36/37/38
Safety: 26-37/39-36
Transport Information: N/A
PSA: 57.53000
LogP: 1.09040
Synthetic route
1486-51-7

p-(benzyloxy)benzoic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With 10% Pd/C; cyclohexa-1,4-diene In ethyl acetate at 100℃; for 0.5h; Microwave irradiation;99%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere;99%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;99%
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave;93%
With triethylammonium formate; palladium on activated charcoal for 1h; Ambient temperature;85%
150-13-0

4-amino-benzoic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
Stage #1: 4-amino-benzoic acid With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
96%
Stage #1: 4-amino-benzoic acid With sodium nitrite In water at 20℃; Milling; Green chemistry;
Stage #2: With water at 80℃; for 0.5h; Neutral conditions; Green chemistry;
71%
With mixture of gaseous nitrogen oxides; water
With sulfuric acid; sodium nitrite Erhitzen des Reaktionsgemisches;
Multi-step reaction with 2 steps
1.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 4 °C / Cooling with ice
1.2: 0.5 h / 4 °C / Cooling with ice
2.1: L-tyrosine / aq. phosphate buffer / pH 7
View Scheme
623-05-2

(4-hydroxyphenyl)methanol

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With oxygen In acetonitrile at 20℃; for 7.5h; Catalytic behavior;97%
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;94%
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 24h; chemoselective reaction;90%
121-98-2

methyl 4-methoxybenzoate

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;93%
With iodine; aluminium In acetonitrile at 80℃; for 18h;91%
With 1-butylpyridinium bromide at 100℃; Microwave irradiation; Neat (no solvent);90%
115595-27-2

4-(n-but-3'-enyloxy)benzoic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;71%
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;71%
586-76-5

4-Bromobenzoic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;99%
Stage #1: 4-Bromobenzoic acid With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide at 100℃; for 36h; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide pH=1 - 2; Inert atmosphere;
91%
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 110℃; for 48h; Inert atmosphere;87%
69-72-7

salicylic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 240℃; for 3h;61%
Multi-step reaction with 2 steps
1: SnCl4
2: sulfuric acid / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: SnCl4
2: NaOH / durch Schmelzen
View Scheme
14047-29-1

4-carboxyphenylboronic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry;100%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Irradiation; Green chemistry;99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 28h; Irradiation;99%
14047-29-1

4-carboxyphenylboronic acid

7722-84-1

dihydrogen peroxide

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;97%
619-58-9

4-iodobenzoic acid

99-96-7

4-hydroxy-benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;
99%
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;95%
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 100℃; for 6h; Reagent/catalyst;94%
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Chemistry

Molecular Formula: C7H6O3
Molecular Weight: 138.12 g/mol
EINECS: 202-804-9 
Index of Refraction: 1.615
Density: 1.375 g/cm3
Flash Point: 171.3 °C
Enthalpy of Vaporization: 61.14 kJ/mol
Boiling Point: 336.2 °C at 760 mmHg
Vapour Pressure: 4.48E-05 mmHg at 25 °C
Melting point: 213-217 °C(lit.)
Water solubility: 5 g/L (20 °C)
Appearance: White to beige crystalline powder
Structure of 4-Hydroxybenzoic acid (CAS NO.99-96-7):
                             
IUPAC Name: 4-Hydroxybenzoic acid
Product Categories: Pharmaceutical Raw Materials;Benzoic Acids (Building Blocks for Liquid Crystals);Functional Materials;Phenols;Aromatics;Impurities;Intermediates & Fine Chemicals;Carboxylic Acids;Alphabetical Listings;Flavors and Fragrances

Uses

 4-Hydroxybenzoic acid (CAS NO.99-96-7) is primarily known as the basis for the preparation of its ESTERS. As parabens, it was used as preservatives in cosmetics.

Production

 4-Hydroxybenzoic acid (CAS NO.99-96-7) is produced commercially from potassium phenoxide and carbon dioxide in the Kolbe-Schmitt reaction. It can also be produced in the laboratory by heating potassium salicylate with potassium carbonate to 240 °C, followed by treating with acid.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 210mg/kg (210mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 260, 1956.
mouse LD50 oral 2200mg/kg (2200mg/kg)   Drug Standards. Vol. 20, Pg. 89, 1952.
mouse LD50 subcutaneous 1050mg/kg (1050mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 128, Pg. 135, 1960.
rat LD50 intraperitoneal 340mg/kg (340mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(1), Pg. 85, 1986.
rat LD50 oral > 10gm/kg (10000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(7), Pg. 53, 1984.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36-36/37/38 
R36:Irritating to eyes. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39-36
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.

Specification

 4-Hydroxybenzoic acid , its cas register number is 99-96-7. It also can be called 4-Hydroxybenzenecarboxylic acid ; Benzoic acid, 4-hydroxy- ; and 4-Hydroxy-benzoesaeure . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, 4-Hydroxybenzoic acid (CAS NO.99-96-7) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases. hydrogen chloride, carbon monoxide, carbon dioxide.

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