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Acetanilide

Acetanilide
Acetanilide structure
CAS No.
103-84-4
Chemical Name:
Acetanilide
Synonyms
ACETANIL;usafek-3;NSC 7636;Phenalgin;USAF ek-3;ANTIFEBRIN;Phenalgene;Acetanilid;NSC 203231;ACETANILIDE
CBNumber:
CB9444812
Molecular Formula:
C8H9NO
Formula Weight:
135.16
MOL File:
103-84-4.mol

Acetanilide 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 
5g/l
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
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
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) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a-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

Acetanilide price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.22344 Acetanilide for synthesis 103-84-4 100 g $26.73 2021-12-16 Buy
Sigma-Aldrich 8.22344 Acetanilide for synthesis 103-84-4 500 g $63.36 2021-12-16 Buy
Sigma-Aldrich 00401 Acetanilide puriss. p.a., ≥99.5% (CHN) 103-84-4 5g $75.7 2021-12-16 Buy
Sigma-Aldrich 1003042 Acetaminophen Related Compound D United States Pharmacopeia (USP) Reference Standard 103-84-4 50mg $1160 2021-12-16 Buy
TCI Chemical A3272 Acetanilide 103-84-4 500G $47 2021-12-16 Buy

Acetanilide 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.

Chemical Properties

Acetanilide orthorhombic plates or scales; or white, shining, crystalline solid or powder. Odorless

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 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.

Uses

manufacture of medicinals and dyes; stabilizer for H2O2 solution; as addition to cellulose ester varnishes.

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.

Preparation

Acetanilide is medicinally important as it is used as febrifuge (antifibrin).
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).

Definition

ChEBI: 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.

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

White to gray solid.

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.

Safety Profile

A human poison by an unspecified route. Poison by ingestion and intravenous routes. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: hallucinations and dstorted perceptions, sleepiness, constipation, cyanosis, respiratory stimulation, hdney damage, me themoglobinemiacarboxyhemoglobinemia, and decreased body temperature. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,. Combustible when exposed to heat or flame. See also ANILINE.

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

Acetanilide Preparation Products And Raw materials

Raw materials

Preparation Products


Acetanilide Suppliers

Global( 293)Suppliers
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View Lastest Price from Acetanilide manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-30 Acetanilide
103-84-4
US $10.00 / PCS 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2021-11-08 Acetanilide
103-84-4
US $10.00 / KG 100g 99% 1000MT/Month Wuhan wingroup Pharmaceutical Co., Ltd
2020-01-01 Acetanilide
103-84-4
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd

Acetanilide Spectrum


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