Acetanilide 1

Acetanilide
Acetanilide
[[Image:Acetanilide.png Acetanilide]]

[[Image:Acetanilide-3D-balls.png ]]

Identifiers

CAS number [1]

103-84-4  

ChemSpider [2]
880  

UNII [3]
SP86R356CC  

EC-number [4]
203-150-7

KEGG [5]
C07565  

ChEMBL [6]
CHEMBL269644  

Jmol-3D images [7]

Image 1

[8] [9]
Properties

Molecular formula C6H5NH(COCH3)

Molar mass 135.17 g/mol

Density 1.219 g/cm

3

Melting point 114.3 ºC (236.7 ºF)

Boiling point 304 °C (579 ºF)

Solubility in water <0.1 g/100 mL at 22 °C

Solubility Soluble in ethanol, diethyl ether, acetone, benzene

log P 1.16 (23 ºC)

Vapor pressure 2 Pa (20 ºC)

[10] [11]
Hazards

MSDS [12]
External MSDS

EU Index Not listed

GHS pictograms

GHS signal word WARNING

GHS hazard statements H302

GHS precautionary statements P264, P270, P301+312, P330, P501

Autoignition 545 ºC (1013 ºF)

temperature
[13]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references
Acetanilide 2

Acetanilide[14] 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,[15] 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.[11] Pure crystals are plate shaped and
colorless to white.

Applications
Acetanilide is used as an inhibitor in hydrogen peroxide 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[16] . It is also a precursor in the synthesis of penicillin and other pharmaceuticals.[9]
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 serendipitously found to possess analgesic as well as antipyretic
properties, and was quickly introduced into medical practice under the name of Antifebrin by A. Cahn and P. Hepp
in 1886.[17] But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to
methemoglobinemia, prompted the search for supposedly less toxic aniline derivatives such as phenacetin.[18] After
several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly
metabolized to paracetamol (USAN: acetaminophen) in the human body, and that it was the paracetamol that was
responsible for the analgesic and antipyretic properties.[19] [20] [21] [22] The observed methemoglobinemia after
acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the
body.[23] Acetanilide is no longer used as a drug in its own right, although the success of its metabolite –
paracetamol (acetaminophen) – is well known.

Notes
[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=103-84-4
[2] http:/ / www. chemspider. com/ 880
[3] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=SP86R356CC
[4] http:/ / ecb. jrc. ec. europa. eu/ esis/ index. php?GENRE=ECNO& ENTREE=203-150-7
[5] http:/ / www. kegg. jp/ entry/ C07565
[6] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL269644
[7] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28Nc1ccccc1%29C
[8] 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.
[9] Acetanilide (http:/ / www. inchem. org/ documents/ sids/ sids/ Acetanilide. pdf), SIDS Initial Assessment Report, Geneva: United Nations
Environment Programme, September 2003, .
[10] HSNO Chemical Classification Information Database (http:/ / www. ermanz. govt. nz/ Chemicals/ ChemicalDisplay.
aspx?SubstanceID=12901), New Zealand Environmental Risk Management Authority, , retrieved 2009-08-26.
Acetanilide 3

[11] Safety data for acetanilide (http:/ / ptcl. chem. ox. ac. uk/ MSDS/ AC/ acetanilide. html), Physical Chemistry Laboratory, University of
Oxford, .
[12] http:/ / physchem. ox. ac. uk/ MSDS/ AC/ acetanilide. html
[13] http:/ / en. wikipedia. org/ wiki/ %3Aacetanilide?diff=cur& oldid=410979569
[14] Acetanilide (http:/ / chemicalland21. com/ lifescience/ phar/ ACETANILIDE. htm), .
[15] See, e.g., The preparation of acetanilide from aniline (http:/ / wwwchem. uwimona. edu. jm/ lab_manuals/ c10expt23. html), 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, doi:10.1021/ed056p488: the latter preparation includes the reduction of
nitrobenzene to aniline.
[16] (http:/ / www. industrialchemistry. info/ 100pagesAddict3. pdf), Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 33
[17] Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med. 7: 561–64.
[18] 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, PMID 17227290.
[19] 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, PMID 20241897.
[20] 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.
[21] Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (http:/ / profiles. nlm. nih. gov/ HH/ A/ A/ A/ D/ _/ hhaaad. pdf), J.
Pharmacol. Exp. Ther. 94 (1): 29–38, PMID 18885611,
[22] 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.
[23] The presence of aniline as an impurity in 19th century batches of acetanilide drugs cannot be ruled out. In this sense as well, paracetamol
(acetaminophen) is safer than acetanilide, as (1) the corresponding impurity would be 4-aminophenol, which is less toxic than aniline; and (2)
in vivo hydrolysis of the amide group in paracetamol appears to be negligible.

References
Article Sources and Contributors 4

Article Sources and Contributors

Acetanilide  Source: http://en.wikipedia.org/w/index.php?oldid=421486115  Contributors: AnakngAraw, Backtable, Beetstra, Benjah-bmm27, Blbq, CaptainVindaloo, Chem-awb, DIUZOMA,
Damian Yerrick, DutchDevil, Edgar181, Fuzzform, Gentgeen, Gogo Dodo, GoldenGoose100, Gracenotes, GregorB, Grrexports, Guitarmankev1, Ihcoyc, Jdolno7brand, Jerome Kelly, MiPe,
Mitchdarcy, Nuno Tavares, Pdcook, Physchim62, Raffinate2, Rallette, Rifleman 82, Rune.welsh, Sayeth, Shaddack, Slobod, Starbane, Studbeefpants, Su-no-G, Tim30, Tjmoel, Velella,
Xasodfuih, 59 anonymous edits

Image Sources, Licenses and Contributors

File:Yes check.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg  License: Public Domain  Contributors: User:Gmaxwell, User:WarX
Image:GHS-pictogram-exclam.svg  Source: http://en.wikipedia.org/w/index.php?title=File:GHS-pictogram-exclam.svg  License: Public Domain  Contributors: User:DrTorstenHenning

License
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