General Description
Odorless white or slightly pink crystals. Bitter taste, leaves a sensation of warmth on the tongue. pH (saturated aqueous solution at 82°F) about 5. Sublimation begins at the melting point.
Reactivity Profile
2-HYDROXYBENZAMIDE(65-45-2) is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical may be sensitive to prolonged exposure to light.
Air & Water Reactions
2-HYDROXYBENZAMIDE darkens on exposure to air. . Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available; however, 2-HYDROXYBENZAMIDE is probably combustible.
Description
Salicylamide is less acidic (pKa 8.2) than other salicylic acid derivatives. Although poorly soluble in water, stable
solutions can be formed at pH 9 through ionization of the phenolic group. It is absorbed from the GI tract on oral
administration and is rapidly metabolized to inactive metabolites by intestinal mucosa, but not by hydrolysis. Activity
appears to reside in the intact molecule. Salicylamide is approximately 40 to 55% plasma protein bound, and it
competes with other salicylates and acetaminophen for glucuronide conjugation, decreasing the extent of conjugation
of these other drugs.
Chemical Properties
white or light pink crystals or powder
Definition
ChEBI: The simplest member of the class of salicylamides derived from salicylic acid.
Hazard
One of the primary side effects associated with Salicylamide is gastrointestinal discomfort. Allergic reactions are another potential side effect. It can also have effects on the liver. Prolonged use or high doses may lead to liver damage, which can present as jaundice (yellowing of the skin or eyes), dark urine, or pale stools.
Clinical Use
Whereas salicylamide is reported to be as effective as aspirin as an
analgetic/antipyretic and is effective in relieving pain associated with arthritic conditions, it does not appear to
possess useful anti-inflammatory activity. Thus, indications for the treatment of arthritic disease states are
unwarranted, and its use is restricted to the relief of minor aches and pain at a dosage of 325 to 650 mg three or four
times per day. Its effects in humans are not reliable, however, and its use is not widely recommended.
Synthesis
A method for the preparation of salicylamide, in a 1000 liter stainless steel reactor, adding 150 kg of methyl salicylate, 420 kg of toluene, heating to 40 ~ 45 ℃, continuous ventilation of ammonia for ammonia reaction, the reaction temperature is control
Purification Methods
Crystallise the amide from water or repeatedly from CHCl3 [Nishiya et al. J Am Chem Soc 108 3880 1986]. [Beilstein 10 IV 169.] The anilide [87-17-2] M 213.2, m 135o crystallises from H2O. [Beilstein 12 H 500, 12 I 268, 12 II 256, 12 944.]
