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Salicylanilide

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Name

Salicylanilide

EINECS 201-727-8
CAS No. 87-17-2 Density 1.278 g/cm3
PSA 49.33000 LogP 2.71750
Solubility slightly soluble in water Melting Point 136-138 °C
Formula C13H11NO2 Boiling Point 294.3 °C at 760 mmHg
Molecular Weight 213.236 Flash Point 131.8 °C
Transport Information N/A Appearance greyish-brownish powder
Safety 26-37/39-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 87-17-2 (Salicylanilide) Hazard Symbols IrritantXi
Synonyms

Salicylanilide(8CI);2-(N-Phenylcarboxamido)phenol;2-Hydroxy-N-phenylbenzamide;Aseptolan;Hyanilid;N-Phenyl-2-hydroxybenzamide;N-Phenylsalicylamide;NSC 14881;SA 88;SA 88 (biocide);Salicylic acid anilide;Salifebrin;Salinidol;Sherstat SLN;Shirlan;Shirlan AG;Shirlan Extra;WR 10019;o-Hydroxybenzanilide;

Article Data 96

Salicylanilide Consensus Reports

Reported in EPA TSCA Inventory.

Salicylanilide Specification

The IUPAC name of Salicylanilide is 2-hydroxy-N-phenylbenzamide. With the CAS registry number 87-17-2, it is also named as 2-N-Phenylcarboxamidophenol; Anilid kyseliny salicylove. It belongs to pharmaceutical intermediates. Furthermore, it is greyish-brownish powder which is soluble in alcohol, ether, benzene and chloroform, and slightly soluble in water.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.26; (4)ACD/LogD (pH 7.4): 2.98; (5)ACD/BCF (pH 5.5): 177.83; (6)ACD/BCF (pH 7.4): 92.14; (7)ACD/KOC (pH 5.5): 1414.8; (8)ACD/KOC (pH 7.4): 733.04; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.675; (13)Molar Refractivity: 62.71 cm3; (14)Molar Volume: 166.7 cm3; (15)Polarizability: 24.86×10-24 cm3; (16)Surface Tension: 58.9 dyne/cm; (17)Enthalpy of Vaporization: 55.53 kJ/mol; (18)Vapour Pressure: 0.00093 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 7; (21)Exact Mass: 213.078979; (22)MonoIsotopic Mass: 213.078979; (23)Topological Polar Surface Area: 49.3; (24)Heavy Atom Count: 16.

Preparation of Salicylanilide: It can be obtained by 2-hydroxy-benzoic acid phenyl ester and aniline with the reagent 1.2.4-trichloro-benzene.

Uses of Salicylanilide: The product is mildew preventive which is mainly used for cotton fabrics and its sodium salt can be used for sheep-line, or inhabited by vinyl chloride and other plastics, rubber, paints, adhesives, leather and other materials of fungicide. Pharmaceutical grade product is used to treat skin diseases and ringworm medicine antisepsis. It also can be used in organic synthesis. For example: It reacts with 3-bromo-2-methyl-propene to get 2-(2-methyl-allyloxy)-N-phenyl-benzamide. This reaction needs reagent potassium carbonate and solvent acetone by heating. The reaction time is 12 hours. The yield is 72%.

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

People can use the following data to convert to the molecule structure. 
1. SMILES: O=C(c1ccccc1O)Nc2ccccc2;
2. InChI: InChI=1/C13H11NO2/c15-12-9-5-4-8-11(12)13(16)14-10-6-2-1-3-7-10/h1-9,15H,(H,14,16).

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 500mg/kg (500mg/kg)   Farmaco. Vol. 44, Pg. 465, 1989.
 
mouse LD50 oral 2400mg/kg (2400mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 663, 1986.

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