| Revision as of 13:01, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465942500 of page Thioacetic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:40, 19 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users1,841 edits Fixes images in dark mode |
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{{Short description|Organosulfur compound (CH3C(O)SH)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 444225850 |
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| verifiedrevid = 470606827 |
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| ImageFileL1= AcSH.svg |
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|ImageFile= Thioacetic-acid-2D-skeletal.png |
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| ImageSizeL1=120 |
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|ImageFile1= Thioacetic-acid-3D-balls.png |
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| ImageClassL1 = skin-invert |
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|ImageSize= |
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| ImageAltL1=Skeletal formula of thioacetic acid |
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|IUPACName=Ethanethioic ''S''-acid |
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|OtherNames=Thioacetic ''S''-acid<br>Thiolacetic acid |
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| ImageFileR1= Thioacetic acid 3D ball.png |
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| ImageSizeR1=120 |
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| ImageAltR1=Ball-and-stick model of the thioacetic acid molecule |
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| PIN=Ethanethioic ''S''-acid<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=97 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames=Thioacetic ''S''-acid<br>Thiolacetic acid |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10052 |
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| ChemSpiderID = 10052 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=507-09-5 |
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| CASNo=507-09-5 |
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| PubChem=10484 |
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| PubChem=10484 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 46800 |
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| ChEBI = 46800 |
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| SMILES = O=C(S)C |
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| SMILES = O=C(S)C |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>2</sub>H<sub>4</sub>OS |
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| Formula={{chem2|CH3C(O)SH}} |
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| MolarMass=76.11756 |
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| MolarMass=76.11756 g/mol |
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| Density=1.08 g/mL |
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| Appearance= |
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| MeltingPtC=-58 |
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| Density=1.08 g/mL |
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| BoilingPtC=93 |
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| MeltingPtC=-58 |
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| Appearance = Transparent, colorless to light yellow liquid<ref name=pubchem>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Thioacetic-acid | title=Thioacetic acid }}</ref><ref name=sigmaaldrich>{{Cite web | url=https://www.sigmaaldrich.com/GB/en/sds/aldrich/t30805 | title=Identification of the substance/mixture and of the company/undertaking - Thioacetic acid | website=www.sigmaaldrich.com}}</ref> |
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| BoilingPtC=93 |
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| Odor = Unpleasant, strong thiol-like |
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| Solubility= |
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| RefractIndex = 1.465 |
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}} |
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| MagSus = −38.4·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section3={{Chembox Hazards |
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| ExternalMSDS = |
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|Section7={{Chembox Hazards |
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| FlashPt= |
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| LD50 = 75 mg/kg (mouse, intraperitoneal) |
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| Autoignition= |
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| MainHazards = May cause severe skin and eye burns. Highly flammable liquid. |
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}} |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|H225|H301|H302|H314|H317}} |
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| PPhrases = {{P-phrases|P210|P233|P240|P241|P242|P243|P260|P261|P264|P264+P265|P270|P272|P280|P301+P316|P301+P317|P301+P330+P331|P302+P352|P302+P361+P354|P303+P361+P353|P304+P340|P305+P354+P338|P316|P317|P321|P330|P333+P317|P362+P364|P363|P370+P378|P403+P235|P405|P501}} |
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| ExternalSDS = |
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'''Thioacetic acid''' is an ] with the ] {{chem2|CH3C(O)SH}}. It is a ]: the sulfur ] of ] ({{chem2|CH3C(O)OH}}), as implied by the '']'' prefix. It is a yellow liquid with a strong ]-like odor. It is used in ] for the introduction of thiol groups ({{chem2|\sSH}}) in molecules.<ref>Jeannie R. Phillips "Thiolacetic Acid" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley. {{doi|10.1002/047084289X.rt096}}</ref> |
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==Synthesis and properties== |
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Thioacetic acid is prepared by the reaction of ] with ]:<ref>{{cite journal|last1=Ellingboe|first1=E. K.|title=Thiolacetic acid|journal=Organic Syntheses|date=1951|volume=31|page=105|doi=10.15227/orgsyn.031.0105}}</ref> |
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:{{chem2|(CH3C(O))2O + H2S → CH3C(O)SH + CH3C(O)OH}} |
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It has also been produced by the action of ] on glacial ], followed by distillation.<ref>{{cite journal |last=Schiff |first=Robert |date=1895-08-09 |title=Preparation of Thioacetic Acid and its Importance for Chemical-Legal Investigations |url=https://books.google.com/books?id=lSLOAAAAMAAJ&pg=PA412 |journal=Chemical News and Journal of Industrial Science |volume=72 |pages=64 |access-date=2016-11-02}}</ref> |
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:{{chem2|CH3C(O)OH + P2S5 → CH3C(O)SH + P2OS4}} |
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Thioacetic acid is typically contaminated by acetic acid. |
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The compound exists exclusively as the thiol ], consistent with the strength of the {{chem2|C\dO}} double bond. Reflecting the influence of ], the ] (93 °C) and melting points are 20 and 75 K lower than those for ]. |
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==Reactivity== |
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===Acidity=== |
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With a p''K''<sub>a</sub> near 3.4, thioacetic acid is about 15 times more acidic than acetic acid.<ref>Matthys J. Janssen "Carboxylic Acids and Esters" in PATAI'S Chemistry of Functional Groups: Carboxylic Acids and Esters, Saul Patai, Ed. pp. 705–764, 1969. {{doi|10.1002/9780470771099.ch15}}</ref> The conjugate base is ]: |
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:{{chem2|CH3C(O)SH → CH3C(O)S− + H+}} |
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In neutral water, thioacetic acid is fully ionized. |
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===Reactivity of thioacetate=== |
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Most of the reactivity of thioacetic acid arises from the conjugate base, thioacetate. Salts of this anion, e.g. ], are used to generate thioacetate esters.<ref>{{cite journal | last = Ervithayasuporn | first = V. | year = 2011 | title = Synthesis and Characterization of Octakis(3-propyl ethanethioate)octasilsesquioxane | journal = ] | volume = 30 | pages = 4475–4478 | doi = 10.1021/om200477a | issue = 17}}</ref> Thioacetate esters undergo hydrolysis to give thiols. A typical method for preparing a thiol from an ] using thioacetic acid proceeds in four discrete steps, some of which can be conducted sequentially in the same flask: |
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:{{chem2|CH3C(O)SH + NaOH → CH3C(O)SNa + H2O}} |
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:{{chem2|CH3C(O)SNa + RX → CH3C(O)SR + NaX}}, where X = Cl, Br, I |
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:{{chem2|CH3C(O)SR + 2 NaOH → CH3CO2Na + RSNa + H2O}} |
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:{{chem2|RSNa + HCl → RSH + NaCl}} |
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In an application that illustrates the use of its radical behavior, thioacetic acid is used with ] in a ] mediated ] to an ] ] forming a ]:<ref>''Synthesis of methyl 6-deoxy-4-O-(sodium sulfonato)-α-L-talopyranoside, its C-4 epimer and both isosteric derivatives ''László Lázár, Magdolna Csávás, Anikó Borbás, Gyöngyi Gyémánt, and András Lipták '']'' '''2004''' (vii) 196-207 </ref> |
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:] |
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==== Reductive acetylation ==== |
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] can be used convert nitroarenes to aryl acetamides in one step. This is particularly useful in the preparation of pharmaceuticals, e.g., ] from ] or 4-nitro].<ref>{{cite journal |last=Bhattacharya |first=Apurba |display-authors=etal |date=2006 |title=One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen |url=http://www.cs.gordon.edu/~ijl/_lead_papers/One%20step%20reductive%20amidation%20of%20nitroarenes%20-%20Tylenol.pdf |journal=Tetrahedron Letters |volume=47 |pages=1861–1864 |doi=10.1016/j.tetlet.2005.09.196 |access-date=2016-11-02 |archive-date=2016-11-04 |archive-url=https://web.archive.org/web/20161104050626/http://www.cs.gordon.edu/~ijl/_lead_papers/One%20step%20reductive%20amidation%20of%20nitroarenes%20-%20Tylenol.pdf |url-status=dead }}</ref> |
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==References== |
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{{reflist}} |
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