240877
p-Toluenesulfonyl chloride
≥99%, solid, ReagentPlus®
Sinónimos:
TsCl, Tosyl chloride
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Fórmula lineal:
CH3C6H4SO2Cl
Número CAS:
Peso molecular:
190.65
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
202-684-8
MDL number:
Beilstein/REAXYS Number:
607898
Assay:
≥99%
Form:
solid
Servicio técnico
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Permítanos ayudarleNombre del producto
p-Toluenesulfonyl chloride, ReagentPlus®, ≥99%
vapor pressure
1 mmHg ( 88 °C)
Quality Level
product line
ReagentPlus®
assay
≥99%
form
solid
bp
134 °C/10 mmHg (lit.)
mp
65-69 °C (lit.)
solubility
benzene: freely soluble(lit.), chloroform: freely soluble(lit.), ethanol: freely soluble(lit.), water: insoluble(lit.)
SMILES string
Cc1ccc(cc1)S(Cl)(=O)=O
InChI
1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
InChI key
YYROPELSRYBVMQ-UHFFFAOYSA-N
General description
p-Toluenesulfonyl chloride is an organic sulfonyl chloride mainly used to convert hydroxyl groups into good leaving group by forming sulfonates.
Application
p-Toluenesulfonyl chloride may be used in the following processes:
- In combination with N-methylimidazole for the esterification or thioesterification of carboxylic acids and alcohols or thiols.
- As an additive to enhance the yield of symmetrical biaryls via palladium chloride catalyzed homo-coupling of arylboronic acids in the absence of ligands.
- As a positive chlorine source for the ?-chlorination of ketones.
- Solvent-free tosylation of alcohols and phenols in the presence of heterodoxy acids.
- As an activator for reaction between 2-alkynylbenzaldoxime and phenols to form 1-aroxyisoquinolines in the presence of silver triflate.
- As a catalyst for the solvent-free preparation of symmetrical bis(benzhydryl)ethers from benzhydrols.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
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
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Clase de almacenamiento
11 - Combustible Solids
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Immobilization of ligands with organic sulfonyl chlorides
Nilsson K & Mosbach K
Methods in Enzymology, 104, 56-69 (1984)
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)
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)