Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
4-(n-but-3'-enyloxy)benzoic acid
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
4-carboxyphenylboronic acid
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique; | 97% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzenecarbonitrile With copper(l) iodide; 5-bromo-2-(1H-imidazol-2-yl)pyridine; water; potassium hydroxide In water; dimethyl sulfoxide; tert-butyl alcohol at 100℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere; | 87% |
1-(4-hydroxy-phenyl)-2-(toluene-4-sulfonyl)-ethanone
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 20 - 50℃; for 4h; | 90% |
1-amino-4-(tris(pyrazol-1-yl)methyl)benzene
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite In water at 100℃; for 0.75h; Concentration; Cooling with ice; | 99.3% |
Conditions | Yield |
---|---|
Stage #1: 4-bromophenyl acetate With bromobenzene; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc In acetonitrile Inert atmosphere; Stage #2: carbon dioxide With palladium diacetate; tricyclohexylphosphine In tetrahydrofuran; acetonitrile at 0℃; under 760.051 Torr; Inert atmosphere; Further stages; | 97% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxycarbonylphenyl bromide With copper(l) iodide; 5-bromo-2-(1H-imidazol-2-yl)pyridine; potassium hydroxide In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere; | 83% |
4-n-decanoyloxybenzoic acid
A
peroxylaurinoic acid
B
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 20℃; pH=10 - 11; | A 100% B n/a |
carbon dioxide
sodium phenoxide
A
salicylic acid
B
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With 2,3-dimethyl-2,3-butane diol In phenol at 120℃; under 4500.45 Torr; for 1h; Autoclave; | A 28.5% B 2.9% |
Stage #1: sodium phenoxide With acetylacetone at 120℃; under 4500.45 Torr; for 1h; Autoclave; Inert atmosphere; Stage #2: carbon dioxide With water at 60℃; for 0.5h; Reagent/catalyst; Autoclave; |
Conditions | Yield |
---|---|
With sodium hydroxide; copper In water at 80℃; for 6h; | 86.5% |
With copper; β‐cyclodextrin In potassium hydroxide at 80℃; for 15h; | 59% |
Conditions | Yield |
---|---|
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube; | 68% |
4-methoxycarbonylphenylboronic acid
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate In water at 20 - 50℃; for 5h; | 47% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetonitrile at 20℃; for 5.3h; Reagent/catalyst; | 96% |
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry; | 95% |
With surface plasmon resonance-activated silver nanocubes; air at 60℃; under 760.051 Torr; for 18h; Wavelength; Irradiation; | 95% |
Conditions | Yield |
---|---|
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h; | 70% |
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In N,N-dimethyl acetamide at 70℃; under 760.051 Torr; | 40% |
Conditions | Yield |
---|---|
With water at 140℃; for 6h; Sealed tube; | A 92% B 8% |
Conditions | Yield |
---|---|
Stage #1: 4-acetoxycinnamic acid amide With oxygen; ozone; acetic acid In water at 0 - 10℃; for 2h; Stage #2: With dihydrogen peroxide In water at 15 - 90℃; for 2h; | A 59% B 36% |
Conditions | Yield |
---|---|
Stage #1: para-coumaric acid With oxygen; ozone; acetic acid In water at 0 - 10℃; for 1.16667h; Stage #2: With dihydrogen peroxide In water at 15 - 95℃; for 3h; | 16% |
With potassium hydroxide fusion; |
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 20 - 50℃; for 4h; | A 45% B 40% |
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-hydroxycinnamic acid amide With oxygen; ozone; acetic acid In water at 0 - 10℃; for 2.5h; Stage #2: With dihydrogen peroxide In water at 15 - 95℃; for 4h; | 37% |
3-(4-acetoxyphenyl)acrylic acid
A
4-acetyloxy-benzoic acid
B
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-(4-acetoxyphenyl)acrylic acid With oxygen; ozone; acetic acid In water at 0 - 10℃; for 1.16667h; Stage #2: With dihydrogen peroxide In water at 15 - 95℃; for 3h; | A 51% B 30% |
Conditions | Yield |
---|---|
With urea-hydrogen peroxide at 141 - 144℃; for 0.0444444h; microwave irradiation; | 70% |
With potassium hydroxide durch Verschmelzen; | |
With potassium hydroxide; lead dioxide at 200 - 220℃; durch Verschmelzen; |
Conditions | Yield |
---|---|
With N-bromophthalimide; mercury(II) diacetate In chloroform at 20℃; for 2h; | 92% |
With tert.-butylhydroperoxide; rhenium(VII) oxide; acetic acid at 100℃; for 5h; | 40% |
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 50h; | 28% |
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran; toluene at 0 - 20℃; for 16h; | 100% |
With Sulfate; titanium(IV) oxide In cyclohexane at 81℃; for 0.166667h; | 98% |
With lanthanum(III) nitrate at 20℃; for 0.333333h; | 97% |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With sulfuric acid for 8h; Heating; | 100% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux; | 100% |
With sodium hydroxide In water; xylene at 85℃; for 1.25h; pH=8 - 10; | 98.05% |
With sodium hydroxide In water; xylene at 85℃; pH=8 - 10; | 98.05% |
tert-butyldimethylsilyl chloride
4-hydroxy-benzoic acid
tert-butyldimethylsilyl 4-((tert-butyldimethylsilyl)oxy)benzoate
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 20℃; for 1h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 16h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With sodium iodide; sodium perchlorate; sodium In methanol | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; | 100% |
In tetrahydrofuran |
chloromethyl methyl ether
4-hydroxy-benzoic acid
4-(methoxymethoxy)benzoic acid
Conditions | Yield |
---|---|
Stage #1: chloromethyl methyl ether; 4-hydroxy-benzoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 17h; Stage #2: With potassium hydroxide In methanol at 20℃; for 3h; Stage #3: With hydrogenchloride In water | 100% |
Stage #1: chloromethyl methyl ether; 4-hydroxy-benzoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 24h; Stage #2: With potassium hydroxide In methanol; water for 3h; Reflux; | 110 g |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 24h; | 100 g |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 24h; | 110 g |
hexamethylenetetramine
4-hydroxy-benzoic acid
3,5-diformyl-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: hexamethylenetetramine; 4-hydroxy-benzoic acid With trifluoroacetic acid for 72h; Reflux; Stage #2: With water at 20 - 80℃; for 4h; | 100% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
With trifluoroacetic acid at 110℃; for 48h; | 70% |
trifluoroacetic acid
4-hydroxy-benzoic acid
3,5-diformyl-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With hexamethylenetetraamine for 72h; Reflux; Inert atmosphere; | 100% |
With hexamethylenetetramine at 110℃; for 48h; Darkness; | 70% |
4-(chlorocarbonyloxy)butyl prop-2-enoate
4-hydroxy-benzoic acid
4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-benzoic acid With sodium hydroxide In water; N,N-dimethyl-formamide pH=10; Stage #2: 4-(chlorocarbonyloxy)butyl prop-2-enoate With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 22h; pH=10; | 100% |
methyl chloroformate
4-hydroxy-benzoic acid
4-(methoxycarbonyloxy)benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; Acylation; | 99% |
With sodium hydroxide In water | 96% |
With sodium hydroxide In water at -5 - 20℃; | 92% |
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h; | 99% |
With tetrabutylammomium bromide; iodine; potassium hydroxide In water at 20℃; for 2.5h; Irradiation; | 94% |
With tetrabutylammomium bromide; caesium carbonate In water at 20℃; for 0.5h; Electrochemical reaction; chemoselective reaction; | 93% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; | 99% |
Stage #1: 4-hydroxy-benzoic acid With sodium hydrogencarbonate In water at 20℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; | 95% |
With potassium hydroxide at 220℃; im geschlossenen Rohr; | |
With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics; |
Conditions | Yield |
---|---|
With sulfuric acid In toluene Esterification; Heating; | 99% |
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 125 - 135℃; for 3h; | 95.3% |
With benzimidazole bisulfate ionic liquid Reflux; | 95.3% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water for 20h; Reflux; | 99% |
With n-Bu4POH In tetrahydrofuran; water at 0 - 20℃; | 94% |
With potassium hydroxide In ethanol; water for 5h; Reflux; | 91% |
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Substitution; | 99% |
Conditions | Yield |
---|---|
With Na-X zeolite In water at 230℃; for 2h; Reagent/catalyst; Temperature; Time; Autoclave; | 99% |
With tetrakis(acetonitrile)palladium(II) tetrafluoroborate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 140℃; for 5h; Autoclave; | 85% |
With Cocos nucifera juice at 20℃; for 48h; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
boric acid In 1,2-dichloro-benzene for 18h; Heating / reflux; | 99% |
With samarium(III) trifluoromethanesulfonate In ethanol; water at 80℃; for 4h; | 85% |
With toluene-4-sulfonic acid In xylene for 4h; Heating; | 46% |
benzyl chloroformate
4-hydroxy-benzoic acid
4-carbobenzoxyoxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water | 99% |
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
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.
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.
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. |
Hazard Codes: Xi
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.
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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