V001581
p-Toluenesulfonyl chloride
99%
Synonym(s):
Tosyl chloride
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About This Item
Linear Formula:
CH3C6H4SO2Cl
CAS Number:
Molecular Weight:
190.65
EC Number:
202-684-8
MDL number:
Beilstein/REAXYS Number:
607898
InChI
1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
InChI key
YYROPELSRYBVMQ-UHFFFAOYSA-N
SMILES string
Cc1ccc(cc1)S(Cl)(=O)=O
vapor pressure
1 mmHg ( 88 °C)
assay
99%
bp
134 °C/10 mmHg (lit.)
Quality Level
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General description
p-Toluenesulfonyl chloride (tosyl chloride or p-TsCl) is an organic sulfonyl chloride mainly used to convert hydroxyl and amine groups into good leaving groups by forming sulfonates.
Application
p-Toluenesulfonyl chloride can be used as:
- An additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of aryl boronic acids in the absence of ligands.
- A chlorine source for the α-chlorination of ketones in the presence of LDA.
- A reactant in the tosylation of alcohols and phenols in the presence of heteropoly acids.
- An activator for the reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.
- A catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1
flash_point_f
262.4 °F - closed cup
flash_point_c
128 °C - closed cup
Storage Class
11 - Combustible Solids
Regulatory Information
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Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts
Fazaeli R, et al.
Canadian Journal of Chemistry, 84(5), 812-818 (2006)
Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p-toluenesulfonyl chloride
Xiao Q, et al.
Tetrahedron, 69(25), 5119-5122 (2013)
Ligandless palladium chloride-catalyzed homo-coupling of arylboronic acids in aqueous media
Kabalka GW & Wang L.
Tetrahedron Letters, 43(16), 3067-3068 (2002)
Facile synthesis of symmetrical bis (benzhydryl) ethers using p-toluenesulfonyl chloride under solvent-free conditions
Brahmachari G & Banerjee B
Organic and Medicinal Chemistry Letters, 3(1), 1-1 (2013)
α-Chlorination of ketones using p-toluenesulfonyl chloride.
Brummond KM and Gesenberg KD.
Tetrahedron Letters, 40(12), 2231-2234 (1999)
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