p-Toluenesulfonyl chloride, 98%, Thermo Scientific Chemicals

Name: p-Toluenesulfonyl chloride, 98%, Thermo Scientific Chemicals
SKU: ALFA14547.30

CAS: 98-59-9 | C7H7ClO2S | 190.64 g/mol

Change view

Quantity:

250 g

500 g

1000 g

Catalog number ALFA14547.30

View Price:

Quantity:

250 g

Request bulk or custom format

Chemical Identifiers

CAS104-88-1

IUPAC Name4-chlorobenzaldehyde

Molecular FormulaC7H5ClO

InChI KeyAVPYQKSLYISFPO-UHFFFAOYSA-N

SMILESClC1=CC=C(C=O)C=C1

Specifications

Specification Sheet

Appearance (Color)White to pale cream or pale yellow

FormCrystals or powder or crystalline powder or fused solid or chunks

Free acid (titration)≤2.5%

Identification (FTIR)Conforms

Melting Point45-49°C (May be cloudy/incomplete melt due to 4-chlorobenzoic acid)

p-Toluenesulfonyl chloride is used as a precursor in the production of dyes and saccharin. It acts as a dehydrating agent in the conversion of urea to carbodiimide and converts alcohols into the corresponding toluenesulfonate esters. It is also employed as a flow-promoting agent for paints, an adhesive, nitrocellulose, coating material and as a plasticizer for polyamides. Furthermore, it serves as an antistatic agent, as a gloss enhancer in plastic film preparations and as a basic material of electroplating solutions.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
p-Toluenesulfonyl chloride is used as a precursor in the production of dyes and saccharin. It acts as a dehydrating agent in the conversion of urea to carbodiimide and converts alcohols into the corresponding toluenesulfonate esters. It is also employed as a flow-promoting agent for paints, an adhesive, nitrocellulose, coating material and as a plasticizer for polyamides. Furthermore, it serves as an antistatic agent, as a gloss enhancer in plastic film preparations and as a basic material of electroplating solutions.

Solubility
Soluble in alcohol, benzene and ether. Insoluble in water.

Notes
Moisture sensitive. Incompatible with strong oxidizing agents and strong bases.

RUO – Research Use Only

General References:

For a detailed study of the optimum conditions for the tosylation of primary and secondary alcohols in pyridine, see: J. Org. Chem., 51, 2386 (1986). For use of 1,4-Diazabicyclo[2.2.2]octane, A14003, as an alternative to pyridine in the tosylation of alcohols, see: Synthesis, 1433 (1997). In the presence of a carboxylic acid, the ester is formed in high yield: J. Am. Chem. Soc., 77, 6214 (1955); 79, 2146 (1957). Esterification of an unprotected amino acid can be effected by heating the tosylate salt with tosyl chloride in an alcohol solvent: J. Org. Chem., 48, 121 (1983).
In the presence of strong bases, 1,2-diols can be converted to epoxides: Synthesis, 706 (1977); 983 (1985); Synth. Commun., 23, 285 (1993), and 1,3-diols to oxetanes: Synthesis, 550 (1981).
N-Tosylation has been used to block the imidazole nucleus in histidine: Bull. Chem. Soc. Jpn., 42, 1466 (1969); 47, 3146 (1974), and arginine residues: Experientia, 24, 661 (1968), during peptide synthesis. Cleavage can be effected with HF. See Appendix 6.
Dehydrating agent, e.g. for conversion of ureas to carbodiimides: Org. Synth. Coll., 5, 555 (1973); Synthesis, 520 (1987).
Cooley, T. A.; Riley, S.; Biros, S. M.; Staples, R. J.; Ngassa, F. N. Crystal structure of 2, 4-dinitrophenyl 4-methylbenzenesulfonate: a new polymorph. Nano lett. 2015, 71 (9), 1085-1088.
Jiang, X.; Yu, G. W.; Li, Z. G.; Chu, S. P.; Wang, S. P. Synthesis and characterisation of phosphazene derivatives containing dioxybiphenyl and 4-sulfanylquinazoline groups. J. Chem. Res., Synop. 2015, 39 (3), 162-165.