14159-48-9

Basic information

• Product Name: propane-2-sulphonic acid
• Synonyms: propane-2-sulphonic acid;Propane-2-sulfonic acid;Einecs 238-001-5
• CAS NO: 14159-48-9
• Molecular Formula: C₃H₈O₃S
• Molecular Weight: 124.15882
• EINECS: 238-001-5
• Mol File: 14159-48-9.mol

Chemical Properties

• Melting Point: -37°C
• Boiling Point: 200.95°C (rough estimate)
• Flash Point: °C
• Appearance: /liquid
• Density: 1.1870
• Refractive Index: 1.4332 (estimate)
• CAS DataBase Reference: propane-2-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: propane-2-sulphonic acid(14159-48-9)
• EPA Substance Registry System: propane-2-sulphonic acid(14159-48-9)

Safety Data

• Hazardous Substances Data: 14159-48-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Propane-2-sulphonic acid is used as a reagent in chemical synthesis for its strong acidic properties, which can facilitate various reactions and improve the yield of desired products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, propane-2-sulphonic acid is used as a buffering agent in the formulation of drugs. Its strong acidic nature allows it to maintain a stable pH environment, which is crucial for the stability and efficacy of certain medications.
Used in Analytical Chemistry:
Propane-2-sulphonic acid is employed as a mobile phase additive in high-performance liquid chromatography (HPLC) and other analytical techniques. Its acidic properties help in the separation and identification of various compounds, making it a valuable tool in research and quality control.
Used in Environmental Applications:
In environmental applications, propane-2-sulphonic acid can be used as a component in the treatment of wastewater. Its strong acidity can help in the removal of pollutants and heavy metals, contributing to a cleaner and safer environment.
Used in Material Science:
In material science, propane-2-sulphonic acid can be used as a modifying agent to alter the properties of polymers and other materials. Its acidic nature can facilitate the formation of new bonds and improve the overall performance of the material.
Overall, propane-2-sulphonic acid is a versatile compound with a wide range of applications across various industries, thanks to its strong acidic properties and ability to interact with different types of molecules.

InChI:InChI=1/C3H8O3S/c1-3(2)7(4,5)6/h3H,1-2H3,(H,4,5,6)

Upstream product

• 75-30-9 2-iodo-propane 
• 625-80-9 diisopropylsulfide 
• 4253-89-8 diisopropyl sulfide 
• 75-33-2 2-propanethiol 
• 75-26-3 isopropyl bromide 
• 64-17-5 ethanol 
• 65167-53-5 Methyl-phosphonothioic acid O-ethyl ester S-isopropyl ester 
• 73761-60-1 propane-2-sulfinic acid 
• 10147-37-2 Isopropylsulfonyl chloride 
• 63873-21-2 O,O-diethyl-S-isopropyl phosphorothiolate 
• 100-51-6 benzyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 31443-08-0 tetramethyl-[1,3]dithietane 
• 7697-37-2 nitric acid 

Downstream Products

• 10147-37-2 Isopropylsulfonyl chloride 

Relevant articles and documents

13C NMR Chemical Shifts of Thiols, Sulfinic Acids, Sulfinyl Chlorides, Sulfonic Acids and Sulfonic Anhydrides

13C NMR spectra of thiols, sulfinic acids, sulfinyl chlorides, sulfonic acids and sulfonic anhydrides have been obtained.The data are dicussed in terms of the additivity of the deshielding effects exerted by the sulfur functionality at the α- or β-position, and the shielding effects produced by the sulfur function at the γ-position.

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

Selective oxidation reactions of diaryl- and dialkyldisulfides to sulfonic acids by CH3ReO3/hydrogen peroxide

Diaryl- and dialkyl disulfides were oxidized in acetonitrile at 20 °C by CH3ReO3/H2O2 oxidant system to yield selectively the corresponding sulfonic acids in short reaction times and in high yields.

The reaction of mercaptans with dimethyldioxirane. A facile synthesis of alkanesulfinic acids

Dimethyldioxirae oxidizes aliphatic thiols to sulfinic acids in very good yield. Benzylic and aromatic thiols give a variety of other oxidation products using DMD.

Mechanisms of hydrolysis and related nucleophilic displacement reactions of alkanesulfonyl chlorides: pH dependence and the mechanism of hydration of sulfenes

pH-rate profiles, primary kinetic isotope effects, deuterium substitution patterns, and pH-product ratios in the presence of added nucleophiles provide evidence for the following overlapping set of mechanisms for the hydrolysis of methanesulfonyl chloride (1) (in 0.1 M KCl at 25 °C): (a) pH ≤ 1-6.7, reaction with water by direct nucleophilic attack on the sulfonyl chloride; (b) pH ≥ 6.7-11.8, rate-determining attack by hydroxide anion to form sulfene (2), which is then trapped by water in a fast step; and (c) pH ≥ 11.8, sulfene formation and sulfene trapping by hydroxide anion; careful inspection showed no sign of sulfene formation in the reaction with water or of direct displacement by hydroxide anion. This pattern, with appropriate variations in the values of pHi (the pH at which two competing mechanisms have the same rate), is apparently general for simple alkanesulfonyl chlorides having at least one hydrogen on the carbon bearing the sulfonyl group. Azide and acetate anions react with 1 below pHi for 1 (6.7) by direct nucleophilic substitution at the sulfur, but above pHi by trapping of the sulfene. 2-Chlorophenoxide anion reacts with 1 below pH 6.7 by both (a) direct displacement to form the ester and (b) elimination to form the sulfene. Above pH 6.7, sulfene is formed from the sulfonyl chloride by reaction with either 2-chlorophenoxide or hydroxide ion; this is followed by trapping of the sulfene with 2-chlorophenoxide, water, or hydroxide. The possibility of the 2-chlorophenoxide anion acting as a general base promoting the reaction of water with either 1 and 2 was examined, but no sign of either process was detected.

MECHANISTIC VARIATION IN ALKANESULFONYL CHLORIDE HYDROLYSIS AND RELATED REACTIONS

Kinetic and product ratio studies are consistent with the following mechanisms for the hydrolysis of methanesulfonyl chloride: (a) in acidic medium (pH 1-6) via a direct substitution on sulfur (SN2-S), (b) in mildly basic medium (pH 8-10) by way of sulfene (CH2=SO2) formation followed by trapping with water, and (c) in strongly basic solution (pH >10) via sulfene with trapping by the hydroxide ion.The reactions of primary and secondary alkanesulfonyl chlorides are qualitatively similar.

REACTION OF PROPOSED PHOSPHOROTHIOLATE S-OXIDE INTERMEDIATES WITH ALCOHOLS

S-Oxide 2 is an extremely reactive intermediate.Its phosphorylation vs rearrangement rates, strongly depend upon the nature of the nucleophile.

Oxidation of thiols and disulfides to sulfonic acids

A process for formation of a sulfonic acid through oxidation of a thiol or disulfide. The process is carried out in the presence of a sulfoxide such as dimethyl sulfoxide, a halogen or hydrogen halide catalyst, and an excess quantity of water. The water acts as a moderator for the oxidation reaction to reduce the level of decomposition of the sulfoxide and, thereby, to improve the overall efficiency of the process. An intermolecular compound of an amino acid containing a sulfonic acid group and a carboxylic acid group with a sulfoxide in which the amino acid is at least moderately soluble. A method which comprises reacting an amino acid containing a sulfonic acid group and a carboxylic acid group with a sulfoxide in which the amino acid is at least moderately soluble. A method for recovering an amino acid containing a sulfonic acid group and a carboxylic acid group from an admixture of the amino acid with other ingredients by adding thereto a sulfoxide in which the amino acid is moderately soluble, with the sulfoxide being added in a sufficient amount to solubilize the amino acid, separating an intermolecular compound of the amino acid with the sulfoxide, and then recovering the amino acid from its intermolecular compound.