| CAS
NO. |
65-45-2 |
|
| EC
NO. |
200-609-3 |
| FORMULA |
C6H4(HO)CONH2 |
| MOL
WT. |
137.14 |
|
H.S.
CODE
|
2924.29 |
|
TOXICITY
|
Oral rat
LD50: 980 mg/kg |
| SYNONYMS |
2-Hydroxybenzamide;
Cetamide;
Salicylic acid amide; |
| 2-Carbamoylphenol;
Amid kyseliny salicylove; o-Hydroxybenzamide;
OHB; 2-hydroxybenzoicacidamide; Salicilamida
(Spanish); |
| SMILES |
|
|
CLASSIFICATION
|
|
|
PHYSICAL AND CHEMICAL PROPERTIES
|
| PHYSICAL
STATE |
white to pink
crystalline powder |
| MELTING POINT |
140 - 144 |
| BOILING
POINT |
181
- 182 C |
| SPECIFIC GRAVITY |
|
| SOLUBILITY
IN WATER |
Soluble in hot water
(soluble in alcohol, ether, chloroform) |
| pH |
acidic |
| VAPOR DENSITY |
|
| AUTOIGNITION |
|
|
REFRACTIVE
INDEX
|
|
| NFPA RATINGS |
Health: 2 Flammability: 1 Reactivity: 0 |
| 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. Salicylamide, amide of salicylic acid, is used as an analgesic, antipyretic, and
antirheumatic drug as well as fungicide. It is also used in manufacturing mordant dyes.
Carbamic acid is a compound of chemical formula H2NCOOH. But it exists only in
the form of carbamate (its salt or ester), carbamide (amide) and carbamoyl (acyl
radical). Carbamate structure inhibits cholinesterase and many insecticides and
parasiticides contain carbamate fuctional group. It is highly toxic to human
also. Heavy exposure to it can cause carbamate poisoning. Natural carbamide
(urea) can be found in protein metabolism in urine. Carbamoyl is the radical
NH2CO-, also called carbamyl. It is involved in the biosynthesis of the
pyrimidine ring. Carbamoyl compounds, such as salicylamides, are important for
the preparation of pharmaceutical products, pesticides, dyes, and biosynthesis researches. |
| SALES
SPECIFICATION |
|
BIBLIOGRAPHY
|
USP
23
|
|
APPEARANCE
|
white to pink
crystalline powder |
|
ASSAY
(HPLC) |
98.0
- 102.0% |
|
MELTING POINT |
139
- 142 C |
|
RESIDUE
ON IGNITION
|
0.1%
max
|
|
LOSS
ON DRYING
|
0.5%
max
|
| TRANSPORTATION |
| PACKING |
25kgs
in fiber drum |
| HAZARD CLASS |
not
regulated |
| UN
NO. |
|
| OTHER
INFORMATION |
|
Hazard
Symbols: XN, Risk Phrases: 22, Safety Phrases: |
GENERAL DESCRIPTION OF AMIDE |
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 กร 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.
|