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{{chembox | {{chembox | ||
| Watchedfields = changed | | Watchedfields = changed | ||
| verifiedrevid = |
| verifiedrevid = 477238648 | ||
| Name = Acetanilide | | Name = Acetanilide | ||
| ImageFile = |
| ImageFile = Acetanilid.svg | ||
| |
| ImageSize = 170 | ||
| |
| ImageFileL1 = Acetanilide Ball and Stick.png | ||
| |
| ImageSizeL1 = 130 | ||
| |
| ImageFileR1 = Acetanilide Space Fill.png | ||
| ImageSizeR1 = 130 | |||
| IUPACName = ''N''-phenylacetamide<br />''N''-phenylethanamide | |||
⚫ | | ImageName = Acetanilide | ||
⚫ | | |
||
| PIN = ''N''-Phenylacetamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 846 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = ''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.| chapter = Front Matter }}</ref> | |||
⚫ | | |
||
| OtherNames = Acetanilide<ref name=iupac2013/><br />''N''-Phenylethanamide | |||
⚫ | |Section1={{Chembox Identifiers | ||
⚫ | | UNII_Ref = {{fdacite|correct|FDA}} | ||
| UNII = SP86R356CC | | UNII = SP86R356CC | ||
| KEGG_Ref = {{keggcite|correct|kegg}} | | KEGG_Ref = {{keggcite|correct|kegg}} | ||
| KEGG = C07565 | | KEGG = C07565 | ||
| Beilstein = 606468 | |||
| Gmelin = 82833 | |||
| InChI = 1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) | | InChI = 1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) | ||
| |
| InChIKey = FZERHIULMFGESH-UHFFFAOYAA | ||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| ChEMBL = 269644 | | ChEMBL = 269644 | ||
Line 23: | Line 28: | ||
| StdInChIKey = FZERHIULMFGESH-UHFFFAOYSA-N | | StdInChIKey = FZERHIULMFGESH-UHFFFAOYSA-N | ||
| CASNo = 103-84-4 | | CASNo = 103-84-4 | ||
| |
| CASNo_Ref = {{cascite|correct|CAS}} | ||
| |
| EC_number = 203-150-7 | ||
| |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| ChemSpiderID = 880 | | ChemSpiderID = 880 | ||
| |
| ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| ChEBI = 28884 | | ChEBI = 28884 | ||
| PubChem = 904 | |||
| RTECS = AD7350000 | |||
| SMILES = O=C(Nc1ccccc1)C | | SMILES = O=C(Nc1ccccc1)C | ||
}} | }} | ||
| |
|Section2={{Chembox Properties | ||
| |
| Properties_ref = <ref>{{RubberBible62nd|page=C-67}}.</ref><ref name="SIDS">{{SIDS-ref | title = Acetanilide | id = Acetanilide | date = September 2003}}.</ref> | ||
| C=8 | H=9 | N=1 | O=1 | |||
| Formula = C<sub>6</sub>H<sub>5</sub>NH(COCH<sub>3</sub>) | |||
| Odor = Odorless | |||
| MolarMass = 135.17 g/mol | |||
| |
| Density = 1.219 g/cm<sup>3</sup> | ||
| MeltingPtC = 113-115 | |||
| MeltingPt = 114.3 ºC (236.7 ºF) | |||
| |
| BoilingPtC = 304 | ||
| Solubility = <0. |
| Dipole = 2.71 | ||
| Solubility = <0.56 g/100 mL (25 °C) | |||
| |
| SolubleOther = Soluble in ], ], ], ] | ||
| |
| LogP = 1.16 (23 °C) | ||
| |
| VaporPressure = 2 Pa (20 °C) | ||
| pKa = 0.5 (25 °C, H<sub>2</sub>O) (conjugate acid)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = ] | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref>}} | |||
}} | |||
| |
|Section7={{Chembox Hazards | ||
| Hazards_ref = <ref name="MSDS">{{cite web| url = http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | archive-url = https://web.archive.org/web/20020623073536/http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | url-status = dead | archive-date = 2002-06-23 | title = Safety data for acetanilide | publisher = Physical Chemistry Laboratory, University of Oxford }}.</ref><ref>{{cite web|title=HSNO Chemical Classification Information Database|url-status=live|url=https://www.epa.govt.nz/database-search/chemical-classification-and-information-database-ccid/view/753A1DBD-C677-44DA-AF65-00F745A42660#:~:text=classification%20acute%20tox.|archive-url=https://web.archive.org/web/20221013183051/https://www.epa.govt.nz/database-search/chemical-classification-and-information-database-ccid/view/753A1DBD-C677-44DA-AF65-00F745A42660#:~:text=classification%20acute%20tox.|archive-date=October 13, 2022|location=New Zealand|publisher=]|access-date=August 26, 2009}}</ref> | |||
| Reference = <ref>{{citation | title = HSNO Chemical Classification Information Database | url = http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=12901 | publisher = New Zealand Environmental Risk Management Authority | accessdate = 2009-08-26 }}.</ref><ref name="MSDS">{{citation | url = http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | title = Safety data for acetanilide | publisher = Physical Chemistry Laboratory, University of Oxford}}.</ref> | |||
| |
| ExternalSDS = | ||
⚫ | | GHSPictograms = {{GHS exclamation mark|Acute Tox. (oral) 4}} | ||
| EUIndex = Not listed | |||
⚫ | | GHSSignalWord = WARNING | ||
⚫ | | |
||
| HPhrases = {{H-phrases|302}} | |||
⚫ | | |
||
| |
| PPhrases = {{P-phrases|264|270|301+312|330|501}} | ||
| FlashPtC = 174 | |||
| PPhrases = {{P-phrases|264|270|301+312|330|501}} | |||
| |
| AutoignitionPtC = 545 | ||
}} | }} | ||
}} | }} | ||
]]] | |||
'''Acetanilide'''<ref>{{citation | url = http://chemicalland21.com/lifescience/phar/ACETANILIDE.htm | title = Acetanilide}}.</ref> is an odourless ] chemical of leaf or flake-like appearance. It is also known as '''N-phenylacetamide''', '''acetanil''', or '''acetanilid''', and was formerly known by the ] '''Antifebrin'''. | |||
'''Acetanilide''' is the ] with the formula {{chem2|C6H5NHC(O)CH3}}. It is the N-acetylated derivative of ].<ref name=Ullmann>{{cite encyclopedia|author1=P. F. Vogt |author2=J. J. Gerulis|title=Amines, Aromatic|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_037|isbn=9783527303854 }}</ref> It is an odourless ] chemical of leaf or flake-like appearance. It is also known as '''''N''-phenylacetamide''', '''acetanil''', or '''acetanilid''', and was formerly known by the ] '''Antifebrin'''. | |||
==Preparation and properties== | ==Preparation and properties== | ||
Acetanilide can be produced by reacting ] with ]: | Acetanilide can be produced by reacting ] with ]:<ref name=Ullmann/> | ||
:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + (CH<sub>3</sub>CO)<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>NHCOCH<sub>3</sub> + CH<sub>3</sub>COOH | :C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + (CH<sub>3</sub>CO)<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>NHCOCH<sub>3</sub> + CH<sub>3</sub>COOH | ||
⚫ | The preparation used to be a traditional experiment in introductory organic chemistry lab classes,<ref>See, e.g., {{citation | title = The preparation of acetanilide from aniline | url = http://wwwchem.uwimona.edu.jm/lab_manuals/c10expt23.html | publisher = Department of Chemistry, University of the West Indies at Mona, Jamaica | |
||
⚫ | The preparation used to be a traditional experiment in introductory organic chemistry lab classes,<ref>See, e.g., {{citation | title = The preparation of acetanilide from aniline | url = http://wwwchem.uwimona.edu.jm/lab_manuals/c10expt23.html | publisher = Department of Chemistry, University of the West Indies at Mona, Jamaica | access-date = 2009-08-26}}; {{citation | first1 = Wilkins | last2 = Lowe | first2 = Valerie C. | title = Preparation of Acetanilide from Nitrobenzene | journal = J. Chem. Educ. | volume = 56 | issue = 7 | pages = 488 | year = 1979 | doi = 10.1021/ed056p488 | last1 = Reeve| bibcode = 1979JChEd..56..488R }}: the latter preparation includes the reduction of nitrobenzene to aniline.</ref> but it has now been widely replaced by the preparation of either ] or ], both of which teach the same practical techniques (especially ] of the product) but which avoid the use of ], a suspected ]. | ||
⚫ | Acetanilide is slightly soluble in water, and stable under most conditions.<ref name="MSDS"/> Pure crystals are plate shaped and colorless |
||
⚫ | Acetanilide is slightly ] in water, and stable under most conditions.<ref name="MSDS"/> Pure crystals are plate shaped and appear colorless, white, or in between. | ||
==Applications== | ==Applications== | ||
Acetanilide is used as an ] |
Acetanilide is used as an ] of ] decomposition and is used to stabilize ] ] ]es.<ref name=Ullmann/> It has also found uses in the intermediation in ] accelerator synthesis, dyes and ] intermediate synthesis, and ] synthesis.<ref>{{Cite web |last=PubChem |title=Acetanilide |url=https://pubchem.ncbi.nlm.nih.gov/compound/904 |access-date=2022-12-10 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the ].<ref>{{cite book | title = Ashford's Dictionary of Industrial Chemicals | edition = Third | year = 2011 | page = 33}}</ref> | ||
In the 19th century acetanilide was one of a large number of compounds used as experimental ]s. | In the 19th century acetanilide was one of a large number of compounds used as experimental ]s. | ||
===Pharmaceutical use=== | ===Pharmaceutical use=== | ||
Acetanilide was the first ] derivative |
Acetanilide was the first ] derivative found to possess ] as well as ] properties, and was quickly introduced into medical practice under the names of Antifebrin by A. Cahn and P. Hepp in 1886.<ref>{{citation | last1 = Cahn | first1 = A. | last2 = Hepp | first2 = P. | title = Das Antifebrin, ein neues Fiebermittel | journal = Centralbl. Klin. Med. | year = 1886 | volume = 7 | pages = 561–64}}.</ref> But its (apparent) unacceptable toxic effects, the most alarming being ] due to ] and ultimately liver and kidney damage,<ref name="Ax&Brodie">{{citation | last1 = Brodie | first1 = B. B. | last2 = Axelrod | first2 = J. | author-link2 = Julius Axelrod | title = 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 | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 22–28 | pmid = 18885610}}.</ref> prompted the search for supposedly less toxic aniline derivatives such as ].<ref name=pmid17227290>{{citation | last1 = Bertolini | first1 = A. | last2 = Ferrari | first2 = A. | last3 = Ottani | first3 = A. | last4 = Guerzoni | first4 = S. | last5 = Tacchi | first5 = R. | last6 = Leone | first6 = S. | title = Paracetamol: new vistas of an old drug | journal = CNS Drug Reviews | year = 2006 | volume = 12 | issue = 3–4 | pages = 250–75 | pmid = 17227290 | doi = 10.1111/j.1527-3458.2006.00250.x| pmc = 6506194 }}.</ref> After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly ] to ] (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties.<ref name="Ax&Brodie"/><ref>Multiple sources: | ||
*{{citation | first1 = D. | last1 = Lester | first2 = L. A. | last2 = Greenberg | title = Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood | journal = J. Pharmacol. Exp. Ther. | year = 1947 | volume = 90 | pages = 68–75 | pmid = 20241897 | issue = 1}}. | |||
*{{citation | last1 = Brodie | first1 = B. B. | last2 = Axelrod | first2 = J. | author-link2 = Julius Axelrod | title = The fate of acetanilide in man | url = http://profiles.nlm.nih.gov/HH/A/A/A/D/_/hhaaad.pdf | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 29–38 | pmid = 18885611}} | |||
*{{citation | first1 = Frederick B. | last1 = Flinn | first2 = Bernard B. | last2 = Brodie | title = The effect on the pain threshold of ''N''-acetyl ''p''-aminophenol, a product derived in the body from acetanilide | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 76–77 | pmid = 18885618}}.</ref> The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is ] to aniline in the body. | |||
== |
==See also== | ||
*] | |||
{{reflist|group="note"}} | |||
==References== | ==References== | ||
{{reflist}} | {{reflist|30em}} | ||
==External links== | |||
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{{cite AV media|url=https://www.youtube.com/watch?v=eQNLmkj_GBo|date=May 21, 2017|title="Making an old pain and fever medication" by NileRed|website=]|people=]}} | |||
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Latest revision as of 04:56, 30 September 2024
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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 | ||
EC Number |
| ||
Gmelin Reference | 82833 | ||
KEGG | |||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
CompTox Dashboard (EPA) | |||
InChI
| |||
SMILES
| |||
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 | |||
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). Y verify (what is ?) Infobox references |
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
- ^ "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.
- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
- 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..
- Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003.
- ^ "Safety data for acetanilide". Physical Chemistry Laboratory, University of Oxford. Archived from the original on 2002-06-23..
- "HSNO Chemical Classification Information Database". New Zealand: Environmental Risk Management Authority. Archived from the original on October 13, 2022. Retrieved August 26, 2009.
- ^ 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.
- 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.
- PubChem. "Acetanilide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-10.
- Ashford's Dictionary of Industrial Chemicals (Third ed.). 2011. p. 33.
- Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med., 7: 561–64.
- ^ 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.
- 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.
- 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.
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