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Basic Information

Molecular Structure:
CAS No.:	118-55-8
Name:	Phenyl salicylate
Article Data:	77
Cas Database

Formula:	C₁₃H₁₀O₃
Molecular Weight:	214.221
Synonyms:	Benzoic acid,2-hydroxy-,esters,phenyl ester;Benzoic acid, 2-hydroxy-, phenyl ester;2-Hydroxybenzoic acid, phenyl ester;Phenyl-2-hydroxybenzoate;Fenylester kyseliny salicylove;Phenylsalicylate;2-Phenoxycarbonylphenol;Phenol salicylate;Musol;Salicylic acid, phenyl ester;Salphenyl;Fenylester kyseliny salicylove [Czech];
EINECS:	204-259-2
Density:	1.25 g/cm³
Melting Point:	41.5 °C
Boiling Point:	306.6 °C at 760 mmHg
Flash Point:	137.3 °C
Solubility:	Water: 1 g/6670 mL
Appearance:	White crystalline solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36-24/25
PSA:	46.53000
LogP:	2.61140

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Synthetic route

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2-(4-Oxo-pentanoyloxy)-benzoic acid phenyl ester

: 118-55-8
phenyl Salicylate

Conditions

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

: 2243-42-7
2-phenoxybenzoic acid

: 118-55-8
phenyl Salicylate

Conditions

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%

: 17954-26-6
1,2-dihydro-2-phenoxycarbonylisoquinoline-1-carbonitrile

: 69-72-7
salicylic acid

: 118-55-8
phenyl Salicylate

Conditions

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

: 69-72-7
salicylic acid

: 108-95-2
phenol

: 118-55-8
phenyl Salicylate

Conditions

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

: 108-95-2
phenol

: 119-36-8
methyl salicylate

: 118-55-8
phenyl Salicylate

Conditions

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;

: 66003-76-7
Diphenyliodonium triflate

: 69-72-7
salicylic acid

: 118-55-8
phenyl Salicylate

Conditions

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%

: 201230-82-2
carbon monoxide

: 108-95-2
phenol

: 118-55-8
phenyl Salicylate

Conditions

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%

: 100-47-0
benzonitrile

: 69-72-7
salicylic acid

: 118-55-8
phenyl Salicylate

Conditions

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

: 102-09-0
bis(phenyl) carbonate

: 118-55-8
phenyl Salicylate

Conditions

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%

: 1003-66-3
phenol-d1

: 201230-82-2
carbon monoxide

: 118-55-8
phenyl Salicylate

Conditions

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%

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Phenyl salicylate with CAS registry number of 118-55-8 is also known as 2-Phenoxycarbonylphenol. The IUPAC name is Phenyl 2-hydroxybenzoate. It belongs to product categories of Aromatic Esters; Functional Materials; Liquid Crystals & Related Compounds; Phenyl Esters (Liquid Crystals). Its EINECS registry number is 204-259-2. In addition, the formula is C₁₃H₁₀O₃ and the molecular weight is 214.22. This chemical is a white crystalline solid and should be sealed in a ventilated, cool place away from light, fire and oxides.

Physical properties about Phenyl salicylate are: (1)ACD/LogP: 3.55; (2)ACD/LogD (pH 5.5): 3.55; (3)ACD/LogD (pH 7.4): 3.53; (4)ACD/BCF (pH 5.5): 295.48; (5)ACD/BCF (pH 7.4): 281.91; (6)ACD/KOC (pH 5.5): 2041.42; (7)ACD/KOC (pH 7.4): 1947.66; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.615; (12)Molar Refractivity: 59.77 cm³; (13)Molar Volume: 171.2 cm³; (14)Surface Tension: 51.8 dyne/cm; (15)Density: 1.25 g/cm³; (16)Flash Point: 137.3 °C; (17)Enthalpy of Vaporization: 56.9 kJ/mol; (18)Boiling Point: 306.6 °C at 760 mmHg; (19)Vapour Pressure: 0.000421 mmHg at 25 °C.

Preparation of Phenyl salicylate: it is prepared by reaction of phenol with salicylic acid. Firstly, the raw material is added to reactor and heated to melt at 128-132 °C for 4 hours under stirring. Meanwhile, phosphorus trichloride is added to the reaction mixture slowly. At last, product is obtained by washing, cooling, crystallization and bleaching.

C₇H₆O₃+C₆H₆O→C₁₃H₁₀O₃+H₂O

Uses of Phenyl salicylate: it is used to produce N-methyl-salicylanilide by reaction with N-methyl-aniline. The reaction occurs at the temperature of 180-200 for 3 hours. The yield is about 69%. What's more, it is used as UV absorber, plasticizer, preservative and also used in drug synthesis, organic synthesis.

Phenyl salicylate is used to produce N-methyl-salicylanilide by reaction with N-methyl-aniline.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. Avoid contact with skin and eyes. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)OC(=O)C2=CC=CC=C2O
2. InChI: InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
3. InChIKey: ZQBAKBUEJOMQEX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intraperitoneal	> 500mg/kg (500mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 149, 1954.
rabbit	LDLo	oral	3gm/kg (3000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
rat	LD50	oral	3gm/kg (3000mg/kg)		Food and Cosmetics Toxicology. Vol. 14, Pg. 837, 1976.