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Acetanilide information


Acetanilide
Acetanilide
Names
Preferred IUPAC name
N-Phenylacetamide[1]
Other names
Acetanilide[1]
N-Phenylethanamide
Identifiers
CAS Number
  • 103-84-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
606468
ChEBI
  • CHEBI:28884 checkY
ChEMBL
  • ChEMBL269644 checkY
ChemSpider
  • 880 checkY
ECHA InfoCard 100.002.864 Edit this at Wikidata
EC Number
  • 203-150-7
Gmelin Reference
82833
KEGG
  • C07565 checkY
PubChem CID
  • 904
RTECS number
  • AD7350000
UNII
  • SP86R356CC checkY
CompTox Dashboard (EPA)
  • DTXSID2022543 Edit this at Wikidata
InChI
  • InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) checkY
    Key: FZERHIULMFGESH-UHFFFAOYSA-N checkY
  • 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[3][4]
Chemical formula
C8H9NO
Molar mass 135.166 g·mol−1
Odor Odorless
Density 1.219 g/cm3
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)[2]
Dipole moment
2.71
Hazards[5][6]
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Acetanilide crystals on a watch glass

Acetanilide[7] 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.

  1. ^ a b "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, FL: 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. ^ Acetanilide, archived from the original on 2007-11-25, retrieved 2007-12-29.

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L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther...

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of acetanilide and phenacetin. In 1947, David Lester and Leon Greenberg found strong evidence that paracetamol was a major metabolite of acetanilide in...

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organic compounds as possible new medicines, following the success of acetanilide ten years earlier. Two years later, Bayer created acetylsalicylic acid...

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Butachlor is a herbicide of the acetanilide class. It is used as a selective pre-emergent herbicide. It is extensively used in India in the form of granules...

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Lidocaine

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prefix instead refers to the fact that the drug is chemically related to acetanilide. As of 2021,[update] lidocaine is not listed by the World Anti-Doping...

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Selenium

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Nitration

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a more controlled nitration of aniline starts with the formation of acetanilide by reaction with acetic anhydride followed by the actual nitration. Because...

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Mehta, S. (25 August 2012). "Metabolism of Paracetamol (Acetaminophen), Acetanilide and Phenacetin | Medicinal Chemistry | PharmaXChange.info". pharmaxchange...

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condition known as methemoglobinemia. Axelrod and Brodie discovered that acetanilide, the main ingredient of these pain-killers, was to blame. They found...

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Coal tar

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derivatives have analgesic (pain-killer) properties. These included acetanilide, phenacetin, and paracetamol aka acetaminophen. Paracetamol may be the...

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Heroin

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