Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 4-Toluenesulfonyl chloride: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477223509

| ImageFile1=P-Toluenesulfonyl chloride structure.svg

| ImageSize1=150

| ImageFile2=Tosyl-chloride-3D-vdW.png|ImageSize2=150

| PIN= 4-Methylbenzene-1-sulfonyl chloride

| OtherNames= Tosyl chloride, ''p''-toluenesulfonyl chloride, ''p''-TsCl, TsCl

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 027KYN78B4

| PubChem=7397

| SMILES = O=S(Cl)(=O)c1ccc(cc1)C

|Section2={{Chembox Properties

| Formula=C₇H₇ClO₂S

| MolarMass= 190.65 g/mol

| Appearance=White solid

| Density=

| MeltingPtC = 65 to 69

| MeltingPt_notes =

| BoilingPtC = 134

| BoilingPt_notes = at 10 mmHg

| Solubility= Reacts with water

|Section3={{Chembox Hazards

| Hazards_ref = <ref>{{Cite web | url=http://chemicalland21.com/specialtychem/finechem/p-TOLUENESULFONYL%20CHLORIDE.htm | title=P-TOLUENESULFONYL CHLORIDE (TOSYL CHLORIDE)}}</ref>

| MainHazards= Releases [[hydrochloric acid|HCl]] on contact with water

| FlashPtC =128

| AutoignitionPtC =

| NFPA-H = 3

| NFPA-F = 1

| NFPA-R = 0

'''4-Toluenesulfonyl chloride''' ('''''p''-toluenesulfonyl chloride''', '''toluene-''p''-sulfonyl chloride''') is an [[organic compound]] with the formula CH₃C₆H₄SO₂Cl. This white, malodorous solid is a [[reagent]] widely used in [[organic synthesis]].<ref name=eEROS>{{ cite encyclopedia | author = Whitaker, D. T. | author2 = Whitaker, K. S. | author3 = Johnson, C. R. | author4 = Haas, J. | title = ''p''-Toluenesulfonyl Chloride | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2006 | publisher = John Wiley | location = New York | doi = 10.1002/047084289X.rt136.pub2 | chapter-url = http://onlinelibrary.wiley.com/o/eros/articles/rt136/frame.html | access-date = 2013-05-28 | archive-url = https://web.archive.org/web/20160305090729/http://onlinelibrary.wiley.com/o/eros/articles/rt136/frame.html | archive-date = 2016-03-05 | url-status = dead | chapter = P-Toluenesulfonyl Chloride | isbn = 978-0471936237 }}</ref> Abbreviated '''TsCl''' or '''TosCl''', it is a derivative of [[toluene]] and contains a [[sulfonyl]] chloride (−SO₂Cl) [[functional group]].

==Uses==

{{main|Tosyl}}

In characteristic manner, TsCl converts [[Alcohol (chemistry)|alcohol]]s (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):

: CH₃C₆H₄SO₂Cl + ROH → CH₃C₆H₄SO₂OR + [[hydrogen chloride|HCl]]

Tosylates can be cleaved with lithium aluminium hydride:

: 4 CH₃C₆H₄SO₂OR + LiAlH₄ → LiAl(O₃SC₆H₄CH₃)₄ + 4 RH

Thus, tosylation followed by reduction allows for removal of a hydroxyl group.

Likewise, TsCl is used to prepare [[Sulfonamide (chemistry)|sulfonamides]] from amines:<ref>{{OrgSynth | author = Ichikawa, J. | author2 = Nadano, R. | author3 = Mori, T. | author4 = Wada, Y. | title = 5-''endo''-''trig'' Cyclization of 1,1-Difluoro-1-alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole | year = 2006 | volume = 83 | pages = 111 | collvol = 11 | collvolpages = 834 | prep = v83p0111 }}</ref>

:CH₃C₆H₄SO₂Cl + R₂NH → CH₃C₆H₄SO₂NR₂ + HCl

The resulting [[sulfonamide (chemistry)|sulfonamide]]s are non-basic and, when derived from primary amines, are even acidic.

TsCl reacts with hydrazine to give [[P-Toluenesulfonyl hydrazide|p-toluenesulfonyl hydrazide]].

The preparation of tosyl esters and amides are conducted in the presence of a base, which absorbs hydrogen chloride. The selection of the base is often crucial to the efficiency of tosylation. Typical bases include [[pyridine]] and [[triethylamine]]. Unusual bases are also used; for example, catalytic amounts of trimethylammonium chloride in the presence of triethylamine is highly effective by virtue of the [[trimethylamine]].<ref name=eEROS/>

==Other reactions==

Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make [[nitrile]]s, [[isocyanide]]s and [[diimide]]s.<ref name=eEROS/> In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH₃C₆H₄SO₂Na.<ref>{{OrgSynth | author = Whitmore, F. C. | author2 = Hamilton, F. H. | title = Sodium Toluenesulfinate | year = 1922 | volume = 2 | pages = 89 | collvol = 1 | collvolpages = 492 | prep = CV1P0492 }}</ref>

==Manufacture==

This reagent is inexpensively available for laboratory use. It is a by-product from the production of [[Arene substitution pattern|ortho]]-toluenesulfonyl chloride (a precursor for the synthesis of the common [[food additive]] and catalyst [[saccharin]]), via the chlorosulfonation of [[toluene]]:<ref>{{ Ullmann | author = Lindner, O. | author2 = Rodefeld, L. | title = Benzenesulfonic Acids and Their Derivatives | doi = 10.1002/14356007.a03_507 }}</ref>

: CH₃C₆H₅ + SO₂Cl₂ → CH₃C₆H₄SO₂Cl + HCl

== Hazards ==

Tosyl chloride is "a corrosive [[lachrymator]]."<ref name=eEROS/>

==References==

{{reflist}}

{{DEFAULTSORT:Toluenesulfonyl chloride, 4-}}

[[Category:Reagents for organic chemistry]]

[[Category:Sulfonyl halides]]

[[Category:p-Tosyl compounds]]

[[Category:Foul-smelling chemicals]]