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p-Toluenesulfonic acid

p-Toluenesulfonic acid (PTSA or pTsOH) or tosylic acid (TsOH) is an


organic compound with the formula CH3C6H4SO3H. It is a white solid that p-Toluenesulfonic acid[1]
is soluble in water, alcohols, and other polar organic solvents. The
CH3C6H4SO2– group is known as the tosyl group and is often abbreviated
as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH.H2O.

As with other sulfonic acids, TsOH is a strong organic acid. It is about one
million times stronger than benzoic acid. It is one of the few strong acids that
is solid and, hence, conveniently weighed.

Contents
Preparation and handling
Tosylates
Reactions
See also Names
References Preferred IUPAC name
4-Methylbenzene-1-sulfonic acid
Other names
Preparation and handling 4-Methylbenzenesulfonic acid
TsOH is prepared on an industrial scale by the sulfonation of toluene. It Tosylic acid
hydrates readily. Common impurities include benzenesulfonic acid and tosic acid
sulfuric acid. Impurities can be removed by recrystallization from its PTSA
concentrated aqueous solution followed by azeotropic drying with toluene.[5] Identifiers

TsOH finds use in organic synthesis as an "organic-soluble" acid catalyst. CAS 104-15-4 (http://www.com
Number
Examples of uses include: monchemistry.org/Chemi
calDetail.aspx?ref=104-1
Acetalization of an aldehyde.[6] 5-4)
Esterification of carboxylic acids.[7]
6192-52-5 (http://www.co
Transesterification of an ester.[8]
mmonchemistry.org/Che
micalDetail.aspx?ref=619
Tosylates 2-52-5) (monohydrate)

Alkyl tosylates are alkylating agents because tosylate is electron- 3D model Interactive image (https://
withdrawing, which makes the tosylate anion a good leaving group. Tosylate
(JSmol)
chemapps.stolaf.edu/jmo
is a pseudohalide. Toluenesulfonate esters undergo nucleophilic attack or l/jmol.php?model=Cc1cc
elimination. Reduction of tosylate esters gives the hydrocarbon. Thus, c%28cc1%29S%28%3D
tosylation followed by reduction allows for the deoxygenation of alcohols. O%29%28%3DO%29O)
ChEBI CHEBI:27849 (https://ww
w.ebi.ac.uk/chebi/searchI
d.do?chebiId=27849)
In a famous and illustrative use of tosylate, 2-norbornyl cation was displaced ChEMBL ChEMBL541253 (https://
from the 7-norbornenyl tosylate. The elimination occurs 1011 faster than the
www.ebi.ac.uk/chembldb/
solvolyisis of anti-7-norbornyl p-toluenesulfonate.[9]
index.php/compound/insp
ect/ChEMBL541253)
ChemSpider 5876 (http://www.chemsp
ider.com/Chemical-Struct
ure.5876.html)
Structures of the 7-norbornenyl DrugBank DB03120 (https://www.dr
cation with p-orbital stabilization.
ugbank.ca/drugs/DB0312
0)
Tosylates are also protecting group for alcohols. They are prepared by
ECHA 100.002.891 (https://ech
combining the alcohol with 4-toluenesulfonyl chloride, usually in an aprotic
InfoCard a.europa.eu/substance-in
solvent, often pyridine.[10]
formation/-/substanceinf
o/100.002.891)
Reactions KEGG C06677 (https://www.keg
g.jp/entry/C06677)

TsOH may be converted to p-toluenesulfonic anhydride by PubChem 6101 (https://pubchem.nc


heating with phosphorus pentoxide.[11]
CID
bi.nlm.nih.gov/compound/
When heated with acid and water, TsOH undergoes hydrolysis to 6101)
toluene:
UNII QGV5ZG5741 (https://fda
CH3C6H4SO3H + H2O → C6H5CH3 + H2SO4 sis.nlm.nih.gov/srs/srsdir
ect.jsp?regno=QGV5ZG5
This reaction is general for aryl sulfonic acids.[12][13]
741)
CompTox DTXSID0026701 (https://
See also Dashboard
comptox.epa.gov/dashbo
(EPA)
Tosyl ard/DTXSID0026701)
Collidinium p-toluenesulfonate
InChI
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h
References 2-5H,1H3,(H,8,9,10)
Key: JOXIMZWYDAKGHI-UHFFFAOYSA-N

InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2
1. Merck Index, 11th Edition, 9459. -5H,1H3,(H,8,9,10)
Key: JOXIMZWYDAKGHI-UHFFFAOYAG
2. Armarego, Wilfred (2003). Purification of Laboratory Chemicals.
Elsevier Science. p. 370. ISBN 0-7506-7571-3. SMILES
3. Guthrie, J. P. Hydrolysis of esters of oxy acids: pKa values for Cc1ccc(cc1)S(=O)(=O)O
strong acids. Can. J. Chem. 1978, 56, 2342-2354.
Properties
4. Eckert, F.; Leito, I.; Kaljurand, I.; Kütt, A.; Klamt, A.; Diedenhofen,
M. Prediction of Acidity in Acetonitrile Solution with COSMO-RS. Chemical C7H8O3S
J. Comput. Chem. 2009, 30, 799-810. doi:10.1002/jcc.21103 (htt formula
ps://doi.org/10.1002%2Fjcc.21103) Molar mass 172.20 g/mol (anhydrous)
5. Perrin, D. D. & Armarego, W. L. F. (1988). Purification of 190.22 g/mol
Laboratory Chemicals. Oxford: Pergamon Press. (monohydrate)
6. H. Griesser, H.; Öhrlein, R.; Schwab, W.; Ehrler, R.; Jäger, V.
Appearance colorless (white) solid
(2004). "3-Nitropropanal, 3-Nitropropanol, and 3-Nitropropanal
Dimethyl Acetal" (http://www.orgsyn.org/demo.aspx?prep=v77p0 Density 1.24 g/cm3
236). Organic Syntheses.; Collective Volume, 10, p. 577
7. Furuta, K. Gao, Q.-z.; Yamamoto, H. (1998). "Chiral Melting 38 °C (100 °F; 311 K)
(Acyloxy)borane Complex-catalyzed Asymmetric Diels-Alder point (anhydrous)[2]
Reaction: (1R)-1,3,4-Trimethyl-3-cyclohexene-1-carboxaldehyde" 103 to 106 °C (217 to
(http://www.orgsyn.org/demo.aspx?prep=cv9p0722). Organic
223 °F; 376 to 379 K)
Syntheses.; Collective Volume, 9, p. 722
(monohydrate)
8. Imwinkelried, R.; Schiess, M.; Seebach, D. (1993). "Diisopropyl
(2S,3S)-2,3-O-isopropylidenetartrate" (http://www.orgsyn.org/de Boiling point 140 °C (284 °F; 413 K) at
mo.aspx?prep=cv8p0201). Organic Syntheses.; Collective 20 mmHg
Volume, 8, p. 201
Solubility in 67 g/100 mL
9. Winstein, S.; Shatavsky, M.; Norton, C.; Woodward, R. B. (1955- water
08-01). "7-Norbornenyl and 7-Norbornyl cations". Journal of the
Acidity (pKa) −2.8 (water) reference for
American Chemical Society. 77 (15): 4183–4184.
doi:10.1021/ja01620a078 (https://doi.org/10.1021%2Fja01620a0 benzenesulfonic acid,[3]
78). ISSN 0002-7863 (https://www.worldcat.org/issn/0002-7863). 8.5 (acetonitrile)[4]
10. "Nucleophilic Substitution" (http://www.chem.ucalgary.ca/courses/
350/Carey5th/Ch08/ch8-10-1.html). Structure
11. L. Field and J. W. McFarland (1963). "p-Toluenesulfonic Molecular tetrahedral at S
Anhydride" (http://www.orgsyn.org/demo.aspx?prep=cv4p0940). shape
Organic Syntheses.; Collective Volume, 4, p. 940
Hazards
12. C. M. Suter (1944). The Organic Chemistry of Sulfur. New York:
John Wiley & Sons. pp. 387–388. Main skin irritant
13. J. M. Crafts (1901). "Catalysis in concentrated solutions". J. Am. hazards
Chem. Soc. 23: 236–249. Safety data External MSDS (http://ha
sheet zard.com/msds/mf/baker/
baker/files/t4030.htm)
R-phrases R36/37/38
(outdated)

S-phrases S26
(outdated)

Related compounds
Related Benzenesulfonic acid
sulfonic Sulfanilic acid
acids
Except where otherwise noted, data are
given for materials in their standard
state (at 25 °C [77 °F], 100 kPa).
verify (what is ?)
Infobox references

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