118-55-8

Basic information

• Product Name: Phenyl salicylate
• Synonyms: SALOL;SALICYLIC ACID PHENYL ESTER;PHENYL 2-HYDROXYBENZOATE;PHENYL SALICYLATE;PHENYL-O-HYDROXYBENZOATE;O-HYDROXYBENZOIC ACID PHENYL ESTER;2-HYDROXYBENZOIC ACID PHENYL ESTER;'LGC' (2411)
• CAS NO: 118-55-8
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.22
• EINECS: 204-259-2
• Product Categories: Aromatic Esters;Functional Materials;Liquid Crystals & Related Compounds;Phenyl Esters (Liquid Crystals);Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Liquid Crystals;Materials Science;Organic and Printed Electronics;Organic Building Blocks
• Mol File: 118-55-8.mol
• Article Data: 39

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 172-173 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Fine Crystalline Powder
• Density: 1.250g/cm3
• Vapor Pressure: 0.000421mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: room temp
• Solubility: dioxane: 0.1 g/mL, clear, colorless
• PKA: 8.71±0.10(Predicted)
• Water Solubility: Soluble in alcohol, ether, chloroform, turpentine, acetone and benzene. Sparingly soluble in chloroformbenzene. Insoluble in wat
• Stability: Light sensitive. Incompatible with strong oxidants. Flammable.
• Merck: 14,7310
• BRN: 393969
• CAS DataBase Reference: Phenyl salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl salicylate(118-55-8)
• EPA Substance Registry System: Phenyl salicylate(118-55-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• RTECS: VO6125000
• TSCA: Yes
• Hazardous Substances Data: 118-55-8(Hazardous Substances Data)

Usage

Description

Phenyl salicylate (chemical formula: C13H10O3) belongs to the family of hydroxybenzoic acid which are compound containing a hydroxybenzoic acid or its derivative. It is manufactured through the chemical reaction between phenol and salicylic acid. Phenyl salicylate has several medical properties. It can be used as analgesic to relieve pain, as an antiseptic with antibacterial effect as well as a kind of antipyretic for the treatment of fever. It is also used for the treatment of inflammation triggered by the lower urinary tract. However, it is no longer commonly applied to human medicine, but is still used in veterinary medicine.

References

https://pubchem.ncbi.nlm.nih.gov/compound/Phenyl_salicylate#section=Top http://www.wisegeek.com/what-are-the-medical-uses-of-phenyl-salicylate.htm

Chemical Properties

Phenyl salicylate is a white crystalline solid with a distinctive aromatic odor and taste. Soluble in ether, benzene and chloroform, soluble in ethanol, almost insoluble in water and glycerol.

Uses

Phenyl salicylate is used as an analgesic and antipyretic. It is also used in the manufacture of polymer plastics, lacquers, waxes, polishes, adhesives, and sunscreen products(suntan oils and cremes). As light absorber to prevent discoloration of plastics. It is also a fragrance ingredient, but has limited use. in veterinary use as an external disinfectant and intestinal antiseptic agent.

Definition

ChEBI: Phenyl salicylate is a benzoate ester that is the phenyl ester of salicylic acid. Also known as salol, it can be formed by heating salicylic acid with phenol and is used in the manufacture of some polymers, lacquers, adhesives, waxes and polishes. It has a role as an ultraviolet filter. It is a benzoate ester, a member of phenols and a member of salicylates. It derives from a salicylic acid.

Preparation

Phenyl salicylate was synthesized by esterification of salicylic acid and phenol in the presence of catalyst sulfuric acid. The esterification liquid is neutralized, washed with water and distilled to obtain the finished product. It also can preparation by the action of phosphorus oxychloride on a mixture of phenol and salicylic acid (Merck Index, 1968).

Toxicity evaluation

The acute oral LD50 value in rats was reported as 3 g/kg and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Levenstein, 1975). The probable LD in man is 50-500 mg/kg. The toxic effects of phenyl salicylate are similar to those of phenol but do not include a corrosive action on the alimentary canal (Dittmer, 1959).

General Description

White crystals. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Incompatible with bromine water, ferric salts, camphor, phenol, chloral hydrate, monobrominated camphor, thymol, or urethane in trituration. .

Fire Hazard

Flash point data for Phenyl salicylate are not available, however Phenyl salicylate is probably combustible.

Pharmacology

Phenyl salicylate was found to have slight analgesic activity against pain stimuli in mice (Kameyama, 1961), but ip administration of 500 mg/kg showed no analgesic action against an electric shock applied to the tails of mice (McKenzie & Beechey, 1962). In vitro studies on cartilage and rat-liver mitochondria have shown that phenyl salicylates are more active than salicylates in uncoupling oxidative phosphorylation (Bostrom, Berntsen & Whitehouse, 1964).

Safety Profile

Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS

Metabolism

According to Baas (1890) from 44 to 96% of a dose (5-8 g) of phenyl salicylate is hydrolysed in man and none of it is found in the faeces. An increase in the ethereal sulphates of the urine after its ingestion is due, no doubt, to the phenol liberated (Williams, 1959). Phenyl salicylate is hydrolysed in the gut primarily to phenol and salicylic acid, which are rapidly absorbed and excreted (Fassett, 1963), but it was not hydrolysed by a partially purified preparation of acetylarylesterase from human plasma (Augustinsson & Ekedahl, 1962). Intestinal absorption and excretion of orally administered phenyl salicylate were studied in rabbits and dogs by analysis of blood and urine samples; oral administration of glucosamine hydrochloride increased the blood concentration of phenyl salicylate but had little effect on urinary excretion (Tanaka, Kojima & Matsubara, 1961).

Purification Methods

Fractionally crystallise salol from its melt, then crystallise it from *benzene. [Beilstein 10 IV 154.]

InChI:InChI=1/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H

Synthetic route

2-(4-Oxo-pentanoyloxy)-benzoic acid phenyl ester (116577-48-1) → phenyl Salicylate (118-55-8)

Conditions	Yield
With sodium metabisulfite; sodium thiosulfate In tetrahydrofuran; water for 0.5h; Product distribution; Ambient temperature; deprotection;	93%

2-phenoxybenzoic acid (2243-42-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
With dipotassium hydrogenphosphate; Lumogen F Orange 240 In acetonitrile at 40℃; for 26h; Catalytic behavior; Reagent/catalyst; Solvent; Wavelength; Irradiation; Inert atmosphere;	92%
With sodium carbonate; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 16h; Quantum yield; Catalytic behavior; Solvent; Concentration; Time; Smiles Aromatic Rearrangement; Irradiation;	75%
With dipotassium peroxodisulfate; potassium trifluoroacetate; silver nitrate In acetonitrile at 130℃; for 36h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Smiles Aromatic Rearrangement; Sealed tube; Inert atmosphere;	64%

1,2-dihydro-2-phenoxycarbonylisoquinoline-1-carbonitrile (17954-26-6) + salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
at 135℃; for 2.5h;	86%

salicylic acid (69-72-7) + phenol (108-95-2) → phenyl Salicylate (118-55-8)

Conditions	Yield
With aluminium trichloride; zinc(II) chloride at 0 - 20℃; for 10h;	85%
With trichlorophosphate at 75 - 80℃; for 4h;	70%
With trichlorophosphate

phenol (108-95-2) + methyl salicylate (119-36-8) → phenyl Salicylate (118-55-8)

Conditions	Yield
With 6% Mo(VI)/ZrO2 coated on сordierite honeycomb monolith for 4h; Reflux;	85%
With sodium
With poisoned SO42-/ZrO2 at 250℃; for 1h;	36.6 %Chromat.
Reflux;

Diphenyliodonium triflate (66003-76-7) + salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Reagent/catalyst; Solvent; Temperature; Molecular sieve; Green chemistry;	85%

carbon monoxide (201230-82-2) + phenol (108-95-2) → phenyl Salicylate (118-55-8)

Conditions	Yield
With rhodium(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,2-bis-(dicyclohexylphosphino)ethane In 1,4-dioxane; toluene at 120℃; under 4500.45 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Pressure; Molecular sieve; Autoclave;	81%

benzonitrile (100-47-0) + salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
With thionyl chloride at 75 - 145℃; for 4h; Temperature;	74%

bis(phenyl) carbonate (102-09-0) → phenyl Salicylate (118-55-8)

Conditions	Yield
With carbon dioxide; n-butylstannoic acid; di(n-butyl)tin oxide at 220℃; under 3750.38 Torr; for 3h; Reagent/catalyst; Pressure; Temperature;	66.9%

phenol-d1 (1003-66-3) + carbon monoxide (201230-82-2) → phenyl Salicylate (118-55-8)

Conditions	Yield
With rhodium(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,2-bis-(dicyclohexylphosphino)ethane In 1,4-dioxane; toluene at 120℃; under 4500.45 Torr; for 24h; Molecular sieve; Autoclave;	65%

[Bis(o-phenoxyphenylcarbonyloxy)iodo]benzene → phenyl Salicylate (118-55-8)

Conditions	Yield
With iodine; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane; benzene at 60 - 70℃; for 2h; Irradiation;	54%

bis(phenyl) carbonate (102-09-0) → xanth-9-one (90-47-1) + phenyl Salicylate (118-55-8) + phenol (108-95-2)

Conditions	Yield
With n-butylstannoic acid at 220℃; under 3750.38 Torr; for 8h; Reagent/catalyst; Pressure; Temperature;	A 31% B 53% C 7%

salicylic acid (69-72-7) + phenylboronic acid (98-80-6) → phenyl Salicylate (118-55-8)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); urea In ethyl acetate at 60℃; for 12h; Chan-Lam reaction;	51%

bis(phenyl) carbonate (102-09-0) → xanth-9-one (90-47-1) + phenyl Salicylate (118-55-8)

Conditions	Yield
With Trichlorbutylstannan at 220℃; under 3750.38 Torr; for 8h;	A 24% B 45%

carbon dioxide (124-38-9) + phenol (108-95-2) → bis(phenyl) carbonate (102-09-0) + phenyl Salicylate (118-55-8)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate; zinc(II) chloride In tetrachloromethane at 120℃; under 22501.8 Torr; for 6h;	A 29.7% B 2.2%
With tetrachloromethane; potassium carbonate at 120℃; under 7500.75 Torr; for 6h;	A 74 %Chromat. B 10.7 %Chromat.
With tetrachloromethane; potassium carbonate at 120℃; under 7500.75 Torr; for 6h;	A 40.8 %Chromat. B 59.2 %Chromat.
With C72H76N2O4P2Ti(2+)*2Cl(1-); potassium carbonate In methanol at 100℃; under 45004.5 Torr; for 8h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;	A 2.88 mmol B 1.18 mmol

carbon dioxide (124-38-9) + potassium phenolate (100-67-4) → bis(phenyl) carbonate (102-09-0) + phenyl Salicylate (118-55-8)

Conditions	Yield
With tetramethylammonium bromide; zinc(II) chloride In tetrachloromethane at 120℃; under 22501.8 Torr; for 6h;	A 2.9% B 23%

2-Trifluoromethanesulfonyloxy-benzoic acid phenyl ester (205178-61-6) → 6H-benzo[c]chromen-6-one (2005-10-9) + phenyl Salicylate (118-55-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium pivalate In N,N-dimethyl acetamide at 80℃; for 10h; Heating;	A 22% B 21%

phosgene (75-44-5) + sodium phenoxide (139-02-6) + sodium salicylate (54-21-7) → phenyl Salicylate (118-55-8)

sodium phenoxide (139-02-6) + sodium salicylate (54-21-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
durch Erhitzen im Phosgenstrom;
durch Erhitzen im Phosgenstrom;

diphenyl sulfite (4773-12-0) + salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
at 230℃; Destillation des entstehenden Wassers;

salicylic acid (69-72-7) → phenyl Salicylate (118-55-8)

Conditions	Yield
at 210 - 230℃;
at 250 - 350℃;
With aluminium trichloride; thionyl chloride Behandeln des Reaktionsprodukts mit Phenol oder mit wss. Natriumphenolat-Loesung;

salicylic acid (69-72-7) → phenyl Salicylate (118-55-8) + phenol (108-95-2)

Conditions	Yield
at 200 - 220℃;

salicylic acid (69-72-7) → phenyl Salicylate (118-55-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + phenol (108-95-2)

Conditions	Yield
at 250 - 350℃;

2-hydroxy-benzoic acid ethyl ester (118-61-6) + phenol (108-95-2) → phenyl Salicylate (118-55-8)

Conditions	Yield
With PPA

phosgene (75-44-5) + sodium salicylate (54-21-7) + phenol (108-95-2) → phenyl Salicylate (118-55-8)

Conditions	Yield
Reaktion von Natriumphenolat;
Reaktion von Natriumphenolat;

phenyl 2-acetoxybenzoate (134-55-4) → phenyl Salicylate (118-55-8)

Conditions	Yield
With 10 percent human plasma In acetonitrile at 37℃; Rate constant; phosphate buffer (pH 7.4); or in undiluted plasma;
With phosphate buffer; hydroxide In 1,4-dioxane; water at 37℃; Rate constant;

tetrachloromethane (56-23-5) + phenol (108-95-2) → (trichloromethoxy)benzene (34888-05-6) + Phenyl 4-hydroxybenzoate (17696-62-7) + phenyl Salicylate (118-55-8) + salicyloyl chloride (1441-87-8)

Conditions	Yield
for 5h; Irradiation; Yield given. Yields of byproduct given;

phenol (108-95-2) + disalicylide → phenyl Salicylate (118-55-8)

Conditions	Yield
at 200℃;

phenyl Salicylate (118-55-8) + ethylenediamine (107-15-3) → N,N'-bis(2-hydroxybenzoyl)ethylenediamine (6345-72-8)

Conditions	Yield
at 180 - 190℃; for 1h;	100%
at 125℃; for 1.5h;	80%
With triethylamine In isopropyl alcohol at 80℃; for 0.5h;	67%
With 1,2,4-Trichlorobenzene

nicotinic anhydride (16837-38-0) + phenyl Salicylate (118-55-8) → 2-nicotinoyloxy-benzoic acid phenyl ester (121985-90-8)

Conditions	Yield
With pyridine	99%

phenyl Salicylate (118-55-8) + n-butyl isocyanide (111-36-4) → phenyl-N-butylcarbamate (3898-47-3) + 3-butyl-3,4-dihydro-2H-1,3-benzoxazine-2,4-dione (162936-60-9)

Conditions	Yield
With dmap; triethylamine In dimethyl sulfoxide for 12h; Ambient temperature;	A n/a B 98%

phenyl Salicylate (118-55-8) + 4-Methyl-3-nitroanilin (119-32-4) → 2-hydroxy-N-(4-methyl-3-nitrophenyl)benzamide

Conditions	Yield
at 20 - 162℃; for 0.0833333h; microwave irradiation;	98%

phenyl Salicylate (118-55-8) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 2-(2-bromobenzyloxy)benzoic acid phenyl ester (1380084-70-7)

Conditions	Yield
With potassium carbonate In acetone Inert atmosphere; Reflux;	98%

(6-bromohexyloxy)-tert-butyldimethylsilane (129368-70-3) + phenyl Salicylate (118-55-8) → 7-((tert-butyldimethylsilyl)oxy)-1-(2-hydroxyphenyl)heptan-1-one

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube;	98%

phenyl Salicylate (118-55-8) + Cyclohexyl isocyanate (3173-53-3) → 3-cyclohexyl-benzo[e][1,3]oxazine-2,4-dione (3417-55-8) + cyclohexylcarbamic acid phenyl ester (56379-88-5)

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide for 72h; Ambient temperature;	A 97% B n/a

phenyl Salicylate (118-55-8) + Isopropyl isocyanate (1795-48-8) → phenyl N-isopropylcarbamate (17614-10-7) + 3-Isopropyl-benzo[e][1,3]oxazine-2,4-dione (159977-54-5)

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide for 45h; Ambient temperature;	A n/a B 97%

N-(1,3-dimethylbutyl)-p-phenylenediamine (54208-70-7) + phenyl Salicylate (118-55-8) → 2-hydroxy-N-[4-[(1,3-dimethylbutyl)amino]phenyl]benzamide

Conditions	Yield
at 20 - 201℃; for 0.0833333h; microwave irradiation;	97%

phenyl Salicylate (118-55-8) + 4-nitro-aniline (100-01-6) → 4'-nitrosalicylanilide (1152-51-8)

Conditions	Yield
at 20 - 205℃; for 0.0666667h; microwave irradiation;	96%

phenyl Salicylate (118-55-8) + 3-nitrobenzoic acid (121-92-6) → phenyl 2-((3-nitrobenzoyl)oxy)benzoate

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h;	96%

phenyl Salicylate (118-55-8) + p-toluidine (106-49-0) → 2-hydroxy-N-(p-tolyl)benzamide (7164-80-9)

Conditions	Yield
at 20 - 157℃; for 0.133333h; microwave irradiation;	95%
With boron trifluoride diethyl etherate In toluene at 20℃;	76%
at 200℃;

phenyl Salicylate (118-55-8) + aniline (62-53-3) → salicylanilide (87-17-2)

Conditions	Yield
at 20 - 171℃; for 0.0666667h; microwave irradiation;	95%
at 180 - 200℃; for 3h;	70%

2,2-bis-{4-(4-aminophenoxy)phenyl}propane (13080-86-9) + phenyl Salicylate (118-55-8) → C41H34N2O6

Conditions	Yield
at 200℃; for 4h;	94.1%

phenyl Salicylate (118-55-8) + N-phenylphenylene-1,4-diamine (101-54-2) → 2-hydroxy-N-(4-(phenylamino)phenyl)benzamide (30313-55-4)

Conditions	Yield
at 20 - 186℃; for 0.0833333h; microwave irradiation;	93%

1,2-dimethoxybenzene (91-16-7) + phenyl Salicylate (118-55-8) → (3,4-dimethoxyphenyl)(2-hydroxyphenyl)methanone

Conditions	Yield
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclo-octa-1,5-diene at 170℃; for 20h; Kinetics; Reagent/catalyst; Temperature; Friedel-Crafts Acylation; Inert atmosphere; Sealed tube; regioselective reaction;	93%

phenyl Salicylate (118-55-8) → salicylic acid (69-72-7)

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; for 12h;	92%
With 2,2'-azobis(isobutyronitrile); bis(tri-n-butyltin)oxide In benzene at 80℃; for 2.5h;	73%
With sodium hydroxide In water; tert-butyl alcohol at 30 - 55℃; Thermodynamic data; Mechanism; reactions in var. solvents, CH3CN, Me2SO), between var. conditions; ΔG(excit), ΔH(excit, ΔS(excit);
With sodium hydroxide; polyoxyethylene 23 lauryl ether In water at 35℃; Kinetics; Further Variations:; Reaction partners;
With ethanol; cetyltrimethylammonim bromide; sodium hydroxide In water at 31.84℃; Kinetics; Mechanism; Reagent/catalyst; Temperature; Micellar solution;

phenyl Salicylate (118-55-8) + 1,4-phenylenediamine (106-50-3) → N-(4-aminophenyl)-2-hydroxybenzamide (3679-65-0) + N,N'-1,4-phenylenebis(2-hydroxybenzamide) (20073-94-3)

Conditions	Yield
at 20 - 210℃; for 0.116667h; microwave irradiation;	A 92% B 6%

methyl 6-bromohexanoate (14273-90-6) + phenyl Salicylate (118-55-8) → methyl 7-(2-hydroxyphenyl)-7-oxoheptanoate (133535-19-0)

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;	92%

phenyl Salicylate (118-55-8) + (bromomethylcyclohexane) (2550-36-9) → 2-cyclohexyl-1-(2-hydroxyphenyl)ethan-1-one (1414926-65-0)

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube;	92%

phenyl Salicylate (118-55-8) + 4,4'-diamino diphenyl methane (101-77-9) → C27H22N2O4

Conditions	Yield
at 200℃; for 4h;	90.8%

1H-benzimidazol-2-amine (934-32-7) + phenyl Salicylate (118-55-8) → N-(benzimidazol-2-yl)salicylamide (61745-68-4)

Conditions	Yield
at 190 - 210℃; for 1.5h;	90%
210 deg C, 1.5 h; ethanol, reflux, 5 min.;	66%
at 210℃; for 1.5h;

2-amino-5,6-dimethylbenzothiazole (29927-08-0) + phenyl Salicylate (118-55-8) → N-(5,6-dimethylbenzothiazol-2-yl)salicylamide (123199-79-1)

Conditions	Yield
210 deg C, 1.5 h; ethanol, reflux, 5 min.;	90%
at 210℃; for 1.5h;

phenyl Salicylate (118-55-8) + 1,4-diaminobutane (110-60-1) → N,N'-(butane-1,4-diyl)bis(2-hydroxybenzamide) (76218-89-8)

Conditions	Yield
at 180℃; for 1.5h;	90%

phenyl Salicylate (118-55-8) + o-toluidine (95-53-4) → 2-hydroxy-N-(2-methylphenyl)benzamide (7133-56-4) + phenol (108-95-2)

Conditions	Yield
With 1,2,4-Trichlorobenzene for 0.5h; Heating / reflux;	A 90% B n/a

phenyl Salicylate (118-55-8) + Methacryloyl chloride (920-46-7) → phenyl 2-(methacryloxy)benzoate (33374-44-6)

Conditions	Yield
With triethylamine In dichloromethane at -15 - 20℃; for 20h; Inert atmosphere;	90%

1-bromo-2-cyclohexylethane (1647-26-3) + phenyl Salicylate (118-55-8) → 3-cyclohexyl-1-(2-hydroxyphenyl)propan-1-one (108975-02-6)

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube;	90%

phenyl Salicylate (118-55-8) + ((6-bromohexyl)oxy)(tert-butyl)diphenylsilane (172995-33-4) → 7-((tert-butyldiphenylsilyl)oxy)-1-(2-hydroxyphenyl)heptan-1-one

Conditions	Yield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube;	90%

Upstream product

• 4773-12-0 diphenyl sulfite 
• 69-72-7 salicylic acid 
• 75-44-5 phosgene 
• 54-21-7 sodium salicylate 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 872274-23-2 2-phosphonooxy-benzoic acid phenyl ester 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 
• 100-67-4 potassium phenolate 
• 119-36-8 methyl salicylate 
• 98-80-6 phenylboronic acid 
• 201230-82-2 carbon monoxide 
• 1003-66-3 phenol-d1 

Downstream Products

• 99841-06-2 N¹-Salicyloylpiperazine 
• 121985-90-8 2-nicotinoyloxy-benzoic acid phenyl ester 
• 2839-84-1 2-[1,2,4]triazolo[4,3-a]quinolin-1-yl-phenol 
• 4447-43-2 2-<2-Hydroxy-benzolamino>-1,3,4-thiadiazol 
• 130234-72-9 N-(methyl-[1,3,4]thiadiazol-2-yl)-salicylamide 
• 123199-78-0 N-(quinolin-3-yl)salicylamide 
• 101622-73-5 N-(benzothiazol-2-yl)salicylamide 
• 94843-54-6 2-hydroxy-N-(4,6-dimethyl-2-pyridinyl)benzamide 
• 36288-93-4 2-[(2-hydroxybenzoyl)amino]ethan-1-amine 
• 87-28-5 2-hydroxyethyl salicylate 
• 14475-26-4 N-salicyloyl-benzamidine 
• 93656-74-7 2,4-Bis-(4-nitro-phenylazo)-phenol 
• 41998-16-7 phenyl 2-chlorobenzoate 
• 10268-63-0 phenyl 5-bromo-2-hydroxybenzoate 

Related news

Thermodynamic studies on the interactions of Phenyl salicylate (cas 118-55-8) in protic solvents at different temperatures09/02/2019

Phenyl salicylate (PS) is employed as a nervous system depressant as well as an intestinal antiseptic owing to its antibacterial activity upon hydrolysis in the small intestine. The study of changes in its physico-chemical properties in different solvents may be helpful in understanding the mech...detailed

Investigation of the melting behavior of the reference materials biphenyl and Phenyl salicylate (cas 118-55-8) by a new type adiabatic scanning calorimeter09/01/2019

Simultaneously measured high-resolution enthalpy and heat capacity data are obtained by means of a novel type Peltier-element-based adiabatic scanning calorimeter that can also operate as a classical adiabatic heat-step calorimeter. Specific enthalpy and specific heat capacity results with 2% un...detailed

Measurement and Correlation of Solid-Liquid Equilibria of Phenyl salicylate (cas 118-55-8) with C4 Alcohols08/30/2019

In an equilibrium vessel, the solid-liquid equilibria (SLE) for three binary mixtures of phenyl salicylate with 1-butanol, 2-butanol, and 2-methyl-1-propanol, respectively, have been measured from 283.15 K to the melting temperature of the solute using a method in which an excess amount of solut...detailed

Evidence of co-operativity in the pre-micellar region in the hydrolytic cleavage of Phenyl salicylate (cas 118-55-8) in the presence of cationic surfactants of CTAB, TTAB and CPC08/29/2019

The effects of cationic surfactants of cetyl trimethyl ammonium bromide (CTAB), tetradecyl trimethyl ammonium bromide (TTAB) and cetyl pyridinium chloride (CPC) on the kinetics of intramolecular general base catalyzed hydrolysis ([OH−] range 0.05–0.1 mol L−1) of phenyl salicylate have been stud...detailed

Photo-Fries rearrangement of Phenyl salicylate (cas 118-55-8) studied by two-dimensional infrared spectroscopy☆08/26/2019

Photo-Fries rearrangement of phenyl salicylate was examined by real-time infrared (IR) monitoring in conjunction with density functional theory (DFT) calculation. Changes in the spectral features were readily captured during the photo-induced chemical reaction of the phenyl salicylate by means o...detailed

Relevant articles and documents

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Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids to access phenolic esters

A Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids with arylboronic acids is described. It represents a facile and practical methodology to access phenolic esters in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxycarbonyl, acetoxy, free phenolic hydroxyl, vinyl, nitro, trifluoromethyl, methoxyl, bromo, chloro, iodo, and acetyl groups.

Synthesis, characterization and catalytic activity studies on cordierite honeycomb coated with ZrO2 based solid super acids

Cordierite honeycomb coated with solid acids such as ZrO2, Mo/ZrO2 and W/ZrO2 were synthesized. These solid acid catalysts were also synthesized in their powder forms. The catalytic materials were characterized for their physicochemical properties such as surface area, surface acidity, crystallinity and morphology by using techniques such as BET, NH3-TPD/n-butylamine back titration, powder XRD and SEM respectively. The catalytic activity of these catalytic materials was determined in an acid catalyzed transesterification reaction of methyl salicylate with phenol to synthesize phenyl salicylate (salol). The effect of concentration of Mo or W ions on ZrO2, nature of the catalyst (whether honeycomb coated or powder form), reaction temperature, reaction time and reusability of the catalytic material in transesterification was studied. Formation of diphenyl ether as a by-product was observed on increasing the concentration of Mo or W ions on ZrO2 and also at higher reaction temperature. The catalytic activity of catalytic materials was correlated with surface acidity and the crystalline phases of catalytic material. Transesterification reactions were also carried out with methyl salicylate and benzyl alcohol or cyclohexanol to synthesize their respective salicylate esters. A probable mechanism of transesterification of methyl salicylate with an alcohol is also proposed. The honeycomb catalysts were found to be efficient, ecofriendly, economical and reusable catalysts compared to their powder forms.

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Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids

We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.

Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize ohydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis(dicyclohexylphosphino)ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis(diphenylphosphino)propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.