SALICYLANILIDE

PRODUCT IDENTIFICATION
CAS NO. 87-17-2

SALICYLANILIDE

EINECS NO. 201-727-8
FORMULA C13H11NO2
MOL WT. 213.24

H.S. CODE

  
SMILES

 

TOXICITY

  
SYNONYMS 2-Hydroxy-N-phenylbenzamide
2-Hydroxybenzanilide Salicilanilida (Spanish)

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE

white to off-white crystalline powde

MELTING POINT 136 - 138 C
BOILING POINT

 

SPECIFIC GRAVITY

 

SOLUBILITY IN WATER Slightly (soluble in alcohol, ether, chloroform)
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

  

REFACTIVE INDEX

 

FLASH POINT

 

STABILITY Stable under normal conditions.

GENERAL DESCRIPTION   & APPLICATIONS
Salicylic Acid is a white crystalline powder or needle-shaped crystals with sweetish taste soluble in acetone, ether, alcohol, boiling water, benzene and turpentine, sparingly soluble in chloroformbenzene, slightly soluble in water melts at 158 C. It is prepared commercially by sodium salicylate which derived from sodium phenolate with carbon dioxide under heating and pressure. It contains both a hydroxyl and a carboxyl group, which react with either an acid or an alcohol. The carboxyl group forms esters with alcohols e.g. methyl salicylate is formed with methanol, which used in food flavorings and preservatives menthyl salicylate is formed with methanol, which is used in suntan lotions phenyl salicylate (called salol) is formed with phenol, which is used as an antiseptic and antipyretic agent. The hydroxyl group reacts with acetic acid to form acetylsalicylic acid (called aspirin). Salicylic Acid is important for the preparation of other pharmaceutical products, dyes, flavours, and preservatives. The sodium salt (Sodium salicylate), a shiny white powder, is used for antiseptics preparations and as a preservative. Salicylic Acid derivatives are used in formulating  flavors, preservatives  and  UV absorbers for food and cosmetics as well as plastics. They are used in manufacturing pharmaceuticals mainly analgestics and antipyretics for the relief of pain and fever. Anilide is an amide in which one or more hydrogens are replaced by phenyl having the C6H5NH2-group. Brominated salicylanilides are used as disinfectants with antibacterial and antifungal activities, used mainly in medicated soaps. Bromsalans are examples:
  • Dibromsalan (CAS #: 87-12-7): 4',5-Dibromosalicylanilide
  • Metabromsalan (CAS #: 2577-72-2): 3,5-Dibromosalicylanilide
  • Tribromsalan (CAS #: 87-10-5): 3,4',5-Tribromosalicylanilide

Some salicylanilide derivatives are used as aromatic amide pesticides and anthelmintics. Some examples of salicylanilide anthelmintics include:

  • Closantel (CAS #: 57808-65-8)
  • Niclosamide Base (CAS #: 50-65-7)
    • Niclosamide Monohydrate (CAS #: 7336-56-2)
    • Niclosamide Ethanolamine salt (CAS #: 1420-04-8)
    • Niclosamide Piperazine salt (CAS #: 34892-17-6)
  • Oxyclozanide (CAS #: 2277-92-1)
  • Rafoxanide  (CAS #: 22662-39-1)
SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98.5 to 101.0 %
MELTING POINT

136 - 138 C

WATER

0.5% max
TRANSPORTATION
PACKING

25kgs in Fiber Drum

HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases: 36/37/38, Safety Phrases: 26/37/39
GENERAL DESCRIPTION OF AMIDE & ANILIDE
Amide is a group of organic chemicals with the general formula RCO-NH2 in which a carbon atom is attached to oxygen in double bond and also attached to an hydroxyl group, where 'R' groups range from hydrogen to various linear and ring structures or a compound with a metal replacing hydrogen in ammonia such as sodium amide, NaNH2. Amides are divided into subclasses according to the number of substituents on nitrogen. The primary amide is formed from by replacement of the carboxylic hydroxyl group by the NH2, amino group. An example is acetamide (acetic acid + amide). Amide is obtained by reaction of an acid chloride, acid anhydride, or ester with an amine. Amides are named with adding '-ic acid' or '-oic acid' from the name of the parent carboxylic acid and replacing it with the suffix 'amide'. Amide can be formed from ammonia (NH3). The secondary and tertiary amides are the compounds which one or both hydrogens in primary amides are replaced by other groups. The names of secondary and tertiary amides are denoted by the replaced groups with the prefix capital N (meaning nitrogen) prior to the names of parent amides. Low molecular weight amides are soluble in water due to the formation of hydrogen bonds. primary amides have higher melting and boiling points than secondary and tertiary amides. Anilide is an amide derived from aniline by substitution of an acyl group for the hydrogen of NH2.  Acetanilide is from acetic acid and aniline. Acetanilide is an odourless, white flake solid or crystalline powder (pure form) soluble in hot water alcohol, ether, chloroform, acetone, glycerol, and benzene melting point 114 C and boiling point 304 C can undergo self-ignite at 545 C, but is otherwise stable under most conditions. Acetanilide which can be obtained by acetylation of aniline undergoes nitration at low temperature and yields highly the para-nitro products. Acetyl group can then be removed by acid-catalyzed hydrolysis to yield para-nitroaniline. Although the activating affection of the amino group can be reduced, the acetyl derivative remains an ortho/para-orientation and activating substituent. Examples of aromatic anilide are benzanilide, C6H5NHCOC6H5 or Carbanilide (N,N'-diphenylcarbamide). Some structural amides are
  • Acetamides
  • Acrylamides
  • Anilides
  • Benzamides
  • Naphthylamides
  • Formamides
  • Lactams
  • Salicylamides
  • Sulfonamides
  • Thioamides
  • Fatty amides

An amide is hydrolyzed to yield an amine and a carboxylic acid under strong acidic conditions. The reverse of this process resulting in the loss of water to link amino acids is wide in nature to form proteins, the principal constituents of the protoplasm of all cells. Acyl halides are the most reactive but amides the least reactive among carboxylic acid derivatives, as in order of " acyl halides > anhydrides > esters ≥ acids > amides" . In homogeneous solvent systems, amides react with water only in the presence of strong acid or base catalysts under heating. Because of the nitrogen non-bonded electron pair with the carbonyl group, amides are very polar and the basicity is weaker than amines. Electrophiles bond to oxygen atom in preference to the nitrogen in an amide. One example of this reaction is the production of nitriles by dehydration of primary amides when treated with thionyl chloride. The addition of water to nitriles (carbon-nitrogen triple bond) gives an amide. Sulfonamides are analogs of amides in which the atom attached to oxygen in double bond is sulfur rather than carbon. Sulfonamides react with alkyl halides, acid halides, sulfonyl halides, epihalohydrins, ketones and aldehydes under basic conditions. Benzamide, the simplest aromatic carboxylic amide, is used in the synthesis of various organic compounds. Polyamide is a polymer containing repeated amide groups such as various kinds of nylon and polyacrylamides.