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A p p e a r a n c e
● C r e a t e a c c o u n t ● L o g i n
P e r s o n a l t o o l s
● C r e a t e a c c o u n t ● L o g i n
P a g e s f o r l o g g e d o u t e d i t o r s l e a r n m o r e ● C o n t r i b u t i o n s ● T a l k
( T o p )
1 P r e p a r a t i o n a n d u s e s
2 T o s y l a t e s
3 R e a c t i o n s
4 S e e a l s o
5 R e f e r e n c e s
T o g g l e t h e t a b l e o f c o n t e n t s
p - T o l u e n e s u l f o n i c a c i d
2 4 l a n g u a g e s
● ت ۆ ر ک ج ه ● Č e š t i n a ● D e u t s c h ● Ε λ λ η ν ι κ ά ● E s p a ñ o l ● E s p e r a n t o ● ف ا ر س ی ● F r a n ç a i s ● ह ि न ् द ी ● B a h a s a I n d o n e s i a ● I t a l i a n o ● M a g y a r ● B a h a s a M e l a y u ● N e d e r l a n d s ● 日 本 語 ● O ʻ z b e k c h a / ў з б е к ч а ● P o l s k i ● P o r t u g u ê s ● Р у с с к и й ● С р п с к и / s r p s k i ● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и ● S u o m i ● S v e n s k a ● 中 文
E d i t l i n k s
● A r t i c l e ● T a l k
E n g l i s h
● R e a d ● E d i t ● V i e w h i s t o r y
T o o l s
T o o l s
A c t i o n s
● R e a d ● E d i t ● V i e w h i s t o r y
G e n e r a l
● W h a t l i n k s h e r e ● R e l a t e d c h a n g e s ● U p l o a d f i l e ● S p e c i a l p a g e s ● P e r m a n e n t l i n k ● P a g e i n f o r m a t i o n ● C i t e t h i s p a g e ● G e t s h o r t e n e d U R L ● D o w n l o a d Q R c o d e ● W i k i d a t a i t e m
P r i n t / e x p o r t
● D o w n l o a d a s P D F ● P r i n t a b l e v e r s i o n
I n o t h e r p r o j e c t s
● W i k i m e d i a C o m m o n s
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
p [1]
Slightly impure sample of the monohydrate
Names
Preferred IUPAC name
4-Methylbenzene-1-sulfonic acid
Other names
4-Methylbenzenesulfonic acidpara -Toluenesulfonic acidp
Identifiers
CAS Number
6192-52-5 Y
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.891
KEGG
PubChem CID
UNII
3BTO78GAFF Y
CompTox Dashboard (EPA )
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10) Y
Key: JOXIMZWYDAKGHI-UHFFFAOYSA-N Y
InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)
Key: JOXIMZWYDAKGHI-UHFFFAOYAG
Properties
Chemical formula
C 7 H 8 O 3 S
Molar mass
172.20 g/mol (anhydrous)
Appearance
colorless (white) solid
Density
1.24 g/cm3
Melting point
105 to 107 °C (221 to 225 °F; 378 to 380 K ) (monohydrate)[2] K ) (anhydrous)[2]
Boiling point
140 °C (284 °F; 413 K ) at 20 mmHg
Solubility in water
67 g/100 mL
Acidity (p K a −2.8 (water) reference for benzenesulfonic acid,[3]
8.5 (acetonitrile )[4]
Structure
Molecular shape
tetrahedral at S
Hazards
Occupational safety and health
Main hazards
skin irritant
GHS labelling[5]
Pictograms
Signal word
Warning
Hazard statements
H315 , H319 , H335
Precautionary statements
P302+P352 , P305+P351+P338
Safety data sheet (SDS)
External MSDS
Related compounds
Related sulfonic acids
Benzenesulfonic acid Sulfanilic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
p PTSA , pTSA , or p tosylic acid (TsOH ) is an organic compound with the formula CH 3 C 6 H 4 SO 3 H alcohols , and other polar organic solvents.[6] 3 C 6 H 4 SO 2 tosyl monohydrate , TsOH. H 2 [6]
As with other aryl sulfonic acids , TsOH is a strong organic acid . It is about one million times stronger than benzoic acid .[6]
Preparation and uses [ edit ]
TsOH is prepared on an industrial scale by the sulfonation of toluene . Common impurities include benzenesulfonic acid and sulfuric acid. TsOH monohydrate contains an amount of water. To estimate the total moisture present as impurity, the Karl Fischer method is used.[citation needed Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.[2]
TsOH finds use in organic synthesis as an "organic-soluble" strong acid. Examples of uses include:
Tosylates [ edit ]
Alkyl tosylates are alkylating agents because tosylate is electron-withdrawing as well as a good leaving group . Tosylate is a pseudohalide . Toluenesulfonate esters undergo nucleophilic attack or elimination . Reduction of tosylate esters gives the hydrocarbon. Thus, tosylation followed by reduction allows for the deoxygenation of alcohols.
Structures of the 7-norbornenyl cation with p-orbital stabilization.
In a famous and illustrative use of tosylate, 2-norbornyl cation was displaced from the 7-norbornenyl tosylate. The elimination occurs 1011 anti -7-norbornyl p [10]
Tosylates are also protecting group for alcohols . They are prepared by combining the alcohol with 4-toluenesulfonyl chloride , usually in an aprotic solvent , often pyridine .[11]
Reactions [ edit ]
CH 3 C 6 H 4 SO 3 2 6 H 5 CH 3 2 SO 4
This reaction is general for aryl sulfonic acids .[13] [14]
See also [ edit ]
References [ edit ]
^ Merck Index , 11th Edition, 9459 .
^ a b c Armarego, W. L. F. (2003). Purification of Laboratory Chemicals (8th ed.). Oxford: Elsevier Science. p. 612. ISBN 978-0-12-805457-4
^ Guthrie, J. P. Hydrolysis of esters of oxy acids: pK a Can. J. Chem . 1978 , 56
^ Eckert, F.; Leito, I.; Kaljurand, I.; Kütt, A.; Klamt, A.; Diedenhofen, M. Prediction of Acidity in Acetonitrile Solution with COSMO-RS. J. Comput. Chem . 2009 , 30 doi :10.1002/jcc.21103
^ GHS: GESTIS 510754
^ a b c Baghernejad, Bita (31 August 2011). "Application of p-toluenesulfonic Acid (PTSA) in Organic Synthesis". Current Organic Chemistry . 15 17 ): 3091–3097. doi :10.2174/138527211798357074 .
^ H. Griesser, H.; Öhrlein, R.; Schwab, W.; Ehrler, R.; Jäger, V. (2004). "3-Nitropropanal, 3-Nitropropanol, and 3-Nitropropanal Dimethyl Acetal" . Organic Syntheses Collected Volumes , vol. 10, p. 577
^ Furuta, K.; Gao, Q.-z.; Yamamoto, H. (1998). "Chiral (Acyloxy)borane Complex-catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-cyclohexene-1-carboxaldehyde" . Organic Syntheses Collected Volumes , vol. 9, p. 722
^ Imwinkelried, R.; Schiess, M.; Seebach, D. (1993). "Diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate" . Organic Syntheses Collected Volumes , vol. 8, p. 201
^ Winstein, S.; Shatavsky, M.; Norton, C.; Woodward, R. B. (1955-08-01). "7-Norbornenyl and 7-Norbornyl cations". Journal of the American Chemical Society . 77 15 ): 4183–4184. doi :10.1021/ja01620a078 . ISSN 0002-7863 .
^ "Nucleophilic Substitution" .
^ L. Field & J. W. McFarland (1963). "p . Organic Syntheses Collected Volumes , vol. 4, p. 940
^ C. M. Suter (1944). The Organic Chemistry of Sulfur . New York: John Wiley & Sons. pp. 387–388.
^ J. M. Crafts (1901). "Catalysis in concentrated solutions" . J. Am. Chem. Soc . 23 4 ): 236–249. doi :10.1021/ja02030a007 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=P-Toluenesulfonic_acid&oldid=1206619628 " C a t e g o r i e s : ● B e n z e n e s u l f o n i c a c i d s ● R e a g e n t s f o r o r g a n i c c h e m i s t r y ● A c i d c a t a l y s t s ● S u l f o n i c a c i d s ● P - T o s y l c o m p o u n d s H i d d e n c a t e g o r i e s : ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e C A S r e g i s t r y n u m b e r s ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s ● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m J a n u a r y 2 0 2 1
● T h i s p a g e w a s l a s t e d i t e d o n 1 2 F e b r u a r y 2 0 2 4 , a t 1 7 : 2 1 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
Y
