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Acetanilid

CAS No.
103-84-4
Chemical Name:
Acetanilid
Synonyms
N-PHENYLACETAMIDE;Acetanilid;Acetoanilide;ACETANIL;ACETYLANILINE;Acetylanilide;N-Acetylaniline;N-phenylethanamide;usafek-3;NSC 7636
CBNumber:
CB00131839
Molecular Formula:
C8H9NO
Molecular Weight:
135.16
MDL Number:
MFCD00008674
MOL File:
103-84-4.mol
MSDS File:
SDS
Last updated:2024-11-02 11:02:01

Acetanilid Properties

Melting point 113-115 °C(lit.)
Boiling point 304 °C(lit.)
Density 1,121 g/cm3
vapor density 4.65 (vs air)
vapor pressure 1 mm Hg ( 114 °C)
refractive index 1.5700 (estimate)
Flash point 173 °C
storage temp. Store below +30°C.
solubility Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether.
form Powder
pka 0.5(at 25℃)
color Off-white to beige to grayish-blue
PH 5-7 (10g/l, H2O, 25℃)
Water Solubility 5 g/L (25 ºC)
Merck 14,50
BRN 606468
Dielectric constant 2.9(22.0℃)
Stability Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
LogP 1.160
CAS DataBase Reference 103-84-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII SP86R356CC
NIST Chemistry Reference Acetamide, N-phenyl-(103-84-4)
EPA Substance Registry System Acetanilide (103-84-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  22-26-36
WGK Germany  1
RTECS  AD7350000
Autoignition Temperature 540 °C
TSCA  Yes
HS Code  29242995
Toxicity LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
NFPA 704
1
1 0

Acetanilid price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.22344 Acetanilide for synthesis 103-84-4 100g $36.1 2024-03-01 Buy
Sigma-Aldrich 8.22344 Acetanilide for synthesis 103-84-4 500g $81.2 2024-03-01 Buy
Sigma-Aldrich 1003042 Acetaminophen Related Compound D United States Pharmacopeia (USP) Reference Standard 103-84-4 50mg $1380 2024-03-01 Buy
Sigma-Aldrich 00401 Acetanilide puriss. p.a., ≥99.5% (CHN) 103-84-4 5g $88.6 2024-03-01 Buy
TCI Chemical A3272 Acetanilide 103-84-4 500G $55 2024-03-01 Buy
Product number Packaging Price Buy
8.22344 100g $36.1 Buy
8.22344 500g $81.2 Buy
1003042 50mg $1380 Buy
00401 5g $88.6 Buy
A3272 500G $55 Buy

Acetanilid Chemical Properties,Uses,Production

Chemical Properties

Acetanilide, also known as Nphenylacetamide, acetanil, or acetanilide is a white to gray solid with molecular formula CH3CONHC6H5. It is an odorless colorless, glossy, crystalline powder or flakes. Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties and was quickly introduced into medical practice (Weast, 1981; Gnanasambandan et al., 2014). Later, it was established that in the human body it is mostly metabolized to paracetamol, this compound being responsible for the analgesic and antipyretic properties of acetanilide (Bertolini et al., 2006; Gnanasambandan et al., 2014). In addition, it was discovered that it has unacceptable toxic effects, so that acetanilide is no longer used as a drug.
Acetanilide flakes
Acetanilide is mainly used as an intermediates in the synthesis of pharmaceuticals and dyes, as an additive for hydrogen peroxide and cellulose ester varnishes, and as a plasticizer in polymer industry as well as accelerator in the rubber industry.

Physical properties

White glossy flake crystal or white crystalline powder. Slightly soluble in cold water, soluble in hot water, methanol, ethanol, ether, chloroform, acetone, glycerol and benzene.

History

The department of internal medicine at the University of Strassburg in the 1880s was noted for its investigations into intestinal worms. Adolf Kussmaul, the director, asked two young assistants, Arnold Cahn and Paul Hepp, to treat patients with naphthalene as it had been used elsewhere as an internal antiseptic. The young doctors were disappointed with the initial results, but Hepp persevered with the naphthalene treatment in a patient suffering from a variety of complaints besides worms. Surprisingly, the fever chart revealed a pronounced antipyretic effect from this treatment. This had not been observed before, but further investigation revealed that Hepp had wrongly been supplied by Kopp’s Pharmacy in Strassburg with acetanilide instead of naphthalene! Cahn and Hepp lost no time in publishing a report on their discovery of a new antipyretic.
For many years after its discovery in 1886, Acetanilide was used as an alternative to aspirin (i.e. acetyl salicylate) - an analgesic (painkiller) and antipyretic (fever reducing) drug to relieve e.g. headache, menstrual pain, and rheumatic pain. Under the name “Acetanilide” it formerly appeared in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that Acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately causing damage to the liver and kidneys. Thus, Acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen (i.e. paracetamol), which is a metabolite of Acetanilide and whose use Axelrod and Brodie suggested in the same study.

Uses

Acetanilide is used as an intermediate in the synthesis of rubber accelerator, dyes and camphor. It is also used in the synthesis of penicillin and other pharmaceutical products. It is involved in the preparation of 4-acetamidobenzenesulfonyl chloride, which is an intermediate during the synthesis of sulfa drugs. Further, it is employed as a experimental photographic developer. In addition to this, it is used to stabilize cellulose ester varnishes.

Definition

ChEBI: Acetanilide is a member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group. It has a role as an analgesic. It is a member of acetamides and an anilide. It is functionally related to an acetic acid.

Application

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and to stabilize cellulose ester varnishes. It is also used in the intermediation of rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs. It is also a precursor in the synthesis of penicillin and other pharmaceuticals. In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
Acetanilide is used as a EOF (electroosmotic flow) marker in the studies of affinity capillary electrophoresis for drug–protein binding.
Acetanilide undergoes palladium-catalyzed cross-coupling reaction to form ortho-acylacetanilide.

Preparation

Acetanilide is prepared from aniline by acetylating it with acetic anhydride in presence of glacial acetic acid. Aniline reacts with acetic anhydride to form Acetanilide by nucleophilic substitution reaction and the reaction is called acetylation.
Synthesis of Acetanilide from aniline
In a 100 ml round bottom flask fitted with a reflux condensor place 5ml of aniline and 10 ml of 1:1 acetic acid and acetic anhydride mixture (5ml acetic acid and 5 ml acetic anhydride). Heat the mixture gently under reflux for 15-20 minutes on oil bath and then pour the contents while still hot with stirring into a 200ml beaker containing 100ml ice cold water. Stir the mixture vigorously to hydrolyse the excess acetic anhydride. After all the acetanilide has precipitated, collct it on buchner funnel and wash with cold water. Recrystallise the crude product from boiling water. If the product is excessively coloured add a pinch of animal charcoal to hot water and filter hot through glass wool/ cotton plug. Pure colourless crystals of acetanilide melts at 114°C (5-5.5g).

World Health Organization (WHO)

Acetanilide, a para-aminophenol derivative with analgesic, antipyretic and weak antiinflammatory activity, was introduced into medicine in 1886. It subsequently proved to be excessively myelosuppressive and has been superseded by safer alternatives.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4533, 1983 DOI: 10.1016/S0040-4039(00)85947-X

General Description

Acetanilide is a white to gray solid. (NTP, 1992)

Air & Water Reactions

Acetanilide is sensitive to prolonged exposure to air . Water insoluble.

Reactivity Profile

Acetanilide is an amide. Flammable gases are formed by the reaction of organic amides 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).

Fire Hazard

Acetanilide is combustible.

Potential Exposure

This amide compound is used in rubber industry as accelerator, in plastics industry as cellulose ester stabilizer, in pharmaceutical manufacture, stabilizer for hydrogen peroxide, azo dye manufacture

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Recrystallise acetanilide from water, aqueous EtOH, *benzene or toluene. [Beilstein 12 IV 373.]

Incompatibilities

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alkyl nitrates, alkalis (liberate aniline), chloral hydrate, phenols, ferric salts

Waste Disposal

Add to flammable solvents (alcohol or benzene) and incinerate. Oxides of nitrogenmay be scrubbed from combustion gases with alkaline solution

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View Lastest Price from Acetanilid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
ACETANILID pictures 2023-11-21 ACETANILID
959-66-0
US $0.00-0.00 / kg 1kg 99% 50000kg Hebei Kingfiner Technology Development Co.Ltd
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