6214-18-2

Basic information

• Product Name: Isopropyl Benzenesulfonate
• Synonyms: Benzenesulfonic Acid 1-Methylethyl Ester;Benzenesulfonic Acid Isopropyl Ester;BENZENESULPHONICACIDISOPROPYLESTER;Isopropyl Besylate
• CAS NO: 6214-18-2
• Molecular Formula: C₉H₁₂O₃S
• Molecular Weight: 200.25500
• Product Categories: Aromatics Compounds;Aromatics;Sulfur & Selenium Compounds;Mutagenesis Research Chemicals
• Mol File: 6214-18-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 307.278°C at 760 mmHg (Cal.) ref.
• Flash Point: 39.637°C (Cal.) ref.
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.143g/cm3 (Cal.) ref.
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.5020
• Storage Temp.: Refrigerator
• Solubility: Soluble in chloroform and ethyl acetate.
• CAS DataBase Reference: Isopropyl Benzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl Benzenesulfonate(6214-18-2)
• EPA Substance Registry System: Isopropyl Benzenesulfonate(6214-18-2)

Safety Data

• RTECS: DB7151080
• Hazardous Substances Data: 6214-18-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Oil

Uses

Different sources of media describe the Uses of 6214-18-2 differently. You can refer to the following data:
1. A sulfonate ester as potential genotoxic impurity in drug substances.
2. A sulfonate ester that acts as a potential effects in drug substances impurity.

InChI:InChI=1/C9H12O3S/c1-8(2)12-13(10,11)9-6-4-3-5-7-9/h3-8H,1-2H3

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 67-63-0 isopropyl alcohol 
• 75-30-9 2-iodo-propane 
• 98-11-3 benzenesulfonic acid 

Downstream Products

• 16596-03-5 N,N'-di-p-tolylformamidine 
• 102537-96-2 isopropyl 2-formylbenzenesulfonate 
• 98-11-3 benzenesulfonic acid 
• 515-42-4 sodium phenylsulfonate 
• 2741-16-4 isopropoxybenzene 
• 102537-97-3 isopropyl toluenesulphonate 
• 102537-98-4 isopropyl 2-(phenylthio)benzenesulfonate 

Relevant articles and documents

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.

Process for preparation of oxyglutaric acid ester derivatives

A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.

Studies on chemical carcinogens and mutagens. XXV. Chemoselectivity of alkyl sulfonates toward 4-(p-nitrobenzyl)pyridine (NBP) in phosphate buffer

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