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Acetanilide

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Acetanilide
Acetanilide
Names
Preferred IUPAC name N-Phenylacetamide
Other names Acetanilide
N-Phenylethanamide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 606468
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.864 Edit this at Wikidata
EC Number
  • 203-150-7
Gmelin Reference 82833
KEGG
PubChem CID
RTECS number
  • AD7350000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)Key: FZERHIULMFGESH-UHFFFAOYSA-N
  • InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)Key: FZERHIULMFGESH-UHFFFAOYAA
SMILES
  • O=C(Nc1ccccc1)C
Properties
Chemical formula C8H9NO
Molar mass 135.166 g·mol
Odor Odorless
Density 1.219 g/cm
Melting point 113–115 °C (235–239 °F; 386–388 K)
Boiling point 304 °C (579 °F; 577 K)
Solubility in water <0.56 g/100 mL (25 °C)
Solubility Soluble in ethanol, diethyl ether, acetone, benzene
log P 1.16 (23 °C)
Vapor pressure 2 Pa (20 °C)
Acidity (pKa) 0.5 (25 °C, H2O) (conjugate acid)
Dipole moment 2.71
Hazards
GHS labelling:
Pictograms Acute Tox. (oral) 4
Signal word Warning
Hazard statements H302
Precautionary statements P264, P270, P301+P312, P330, P501
Flash point 174 °C (345 °F; 447 K)
Autoignition
temperature
545 °C (1,013 °F; 818 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound
Acetanilide crystals on a watch glass

Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. It is the N-acetylated derivative of aniline. It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.

Preparation and properties

Acetanilide can be produced by reacting acetic anhydride with aniline:

C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOH

The preparation used to be a traditional experiment in introductory organic chemistry lab classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen.

Acetanilide is slightly soluble in water, and stable under most conditions. Pure crystals are plate shaped and appear colorless, white, or in between.

Applications

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. It has also found uses in the intermediation in 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.

In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.

Pharmaceutical use

Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the names of Antifebrin by A. Cahn and P. Hepp in 1886. But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia and ultimately liver and kidney damage, prompted the search for supposedly less toxic aniline derivatives such as phenacetin. After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties. The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body.

See also

References

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 846. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. N-Phenyl derivatives of primary amides are called 'anilides' and may be named using the term 'anilide' in place of 'amide' in systematic or retained names of amides. (…) However, names expressing N-substitution by a phenyl group on an amide are preferred IUPAC names.
  2. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
  3. Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-67. ISBN 0-8493-0462-8..
  4. Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003.
  5. ^ "Safety data for acetanilide". Physical Chemistry Laboratory, University of Oxford. Archived from the original on 2002-06-23..
  6. "HSNO Chemical Classification Information Database". New Zealand: Environmental Risk Management Authority. Archived from the original on October 13, 2022. Retrieved August 26, 2009.
  7. ^ P. F. Vogt; J. J. Gerulis (2005). "Amines, Aromatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_037. ISBN 9783527303854.
  8. See, e.g., The preparation of acetanilide from aniline, Department of Chemistry, University of the West Indies at Mona, Jamaica, retrieved 2009-08-26; Reeve, Wilkins; Lowe, Valerie C. (1979), "Preparation of Acetanilide from Nitrobenzene", J. Chem. Educ., 56 (7): 488, Bibcode:1979JChEd..56..488R, doi:10.1021/ed056p488: the latter preparation includes the reduction of nitrobenzene to aniline.
  9. PubChem. "Acetanilide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-10.
  10. Ashford's Dictionary of Industrial Chemicals (Third ed.). 2011. p. 33.
  11. Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med., 7: 561–64.
  12. ^ Brodie, B. B.; Axelrod, J. (1948), "The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and total conjugated) in biological fluids and tissues", J. Pharmacol. Exp. Ther., 94 (1): 22–28, PMID 18885610.
  13. Bertolini, A.; Ferrari, A.; Ottani, A.; Guerzoni, S.; Tacchi, R.; Leone, S. (2006), "Paracetamol: new vistas of an old drug", CNS Drug Reviews, 12 (3–4): 250–75, doi:10.1111/j.1527-3458.2006.00250.x, PMC 6506194, PMID 17227290.
  14. Multiple sources:
    • Lester, D.; Greenberg, L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther., 90 (1): 68–75, PMID 20241897.
    • Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (PDF), J. Pharmacol. Exp. Ther., 94 (1): 29–38, PMID 18885611
    • Flinn, Frederick B.; Brodie, Bernard B. (1948), "The effect on the pain threshold of N-acetyl p-aminophenol, a product derived in the body from acetanilide", J. Pharmacol. Exp. Ther., 94 (1): 76–77, PMID 18885618.

External links

NileRed (May 21, 2017). "Making an old pain and fever medication" by NileRed. YouTube.

Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
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See also
Receptor/signaling modulators
Leukotriene signaling modulators
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