2386-47-2

Basic information

• Product Name: 1-Butanesulfonic acid
• Synonyms: butane-1-sulfonic acid;BUTANESULFONIC ACID;1-BUTANESULFONIC ACID;Butane-1-sulphonic acid;BUTANESULPHONICACID;1-Butanesulfonic acid,99%,pract.;2386-54-1 (Hydrochloride salt);Einecs 219-198-7
• CAS NO: 2386-47-2
• Molecular Formula: C₄H₁₀O₃S
• Molecular Weight: 138.19
• EINECS: 219-198-7
• Mol File: 2386-47-2.mol

Chemical Properties

• Melting Point: -15.1°C
• Boiling Point: 223.6°C (rough estimate)
• Appearance: /liquid
• Density: 1.1850
• Refractive Index: 1.4640 (estimate)
• PKA: 1.92±0.50(Predicted)
• Stability: Incompatible with strong oxidizing agents, bases.
• CAS DataBase Reference: 1-Butanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanesulfonic acid(2386-47-2)
• EPA Substance Registry System: 1-Butanesulfonic acid(2386-47-2)

Safety Data

• Hazardous Substances Data: 2386-47-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Butanesulfonic acid is used as a reagent in the chemical synthesis of various organic compounds. Its strong acidic properties and solubility in organic solvents make it a suitable catalyst or reactant in the production of pharmaceuticals, dyes, and other specialty chemicals.
Used in Analytical Chemistry:
1-Butanesulfonic acid is used as a mobile phase additive in high-performance liquid chromatography (HPLC) and other analytical techniques. Its ability to interact with various analytes and improve peak shape and resolution makes it a valuable tool in the separation and identification of complex mixtures.
Used in Environmental Applications:
1-Butanesulfonic acid is used as a component in the treatment of industrial wastewater and soil remediation processes. Its strong acidic properties and ability to form complexes with heavy metals and other pollutants make it an effective agent for the removal of contaminants from the environment.
Used in Material Science:
1-Butanesulfonic acid is used as a functional group in the synthesis of novel materials, such as ion-exchange resins and specialty polymers. Its unique chemical properties contribute to the development of materials with enhanced performance characteristics, such as improved thermal stability and chemical resistance.

Synthesis Reference(s)

Tetrahedron Letters, 4, p. 1131, 1963 DOI: 10.1039/jr9630005127

InChI:InChI=1/C4H10O3S.Na/c1-2-3-4-8(5,6)7;/h2-4H2,1H3,(H,5,6,7);/q;+1/p-1

Upstream product

• 109-65-9 1-bromo-butane 
• 109-79-5 n-butanethiol 
• 109-69-3 n-Butyl chloride 
• 629-45-8 dibutyl disulfide 
• 54829-33-3 S-n-butyl cyclohexanecarbothioate 
• 18032-97-8 diethyl-thiophosphinsaeure-S-n-butylester 
• 50728-05-7 Ethyl-thiophosphonsaeure-O-ethyl-S-n-butylester 
• 56-23-5 tetrachloromethane 
• 106-97-8 n-butane 
• 1404369-06-7 1-(butane-1-ylsulfonoyloxy)-2(1H)-quinolone 
• 1413781-13-1 N-(1-butanesulfonyloxy)anthracene-1,9-dicarboximide 
• 1309926-94-0 o-(butanesulfonoxy) benzanilide 
• 1309926-91-7 o-(butanesulfonoxy) acetanilide 
• 544-40-1 Dibutyl sulfide 

Downstream Products

• 629-45-8 dibutyl disulfide 
• 62926-90-3 2-Methoxy-6-<(methylthio)methyl>aniline 
• 103578-32-1 N-(p-chloro-α,α,α-trifluoro-o-tolyl)S,S-dimethylsulfilimine 
• 179863-07-1 4-(3-methylimidazolium)butanesulfonate 
• 4299-07-4 2-butyl-1,2-benzothiazolin-3-one 
• 2374-69-8 butane-1-sulfonic acid methyl ester 
• 7269-35-4 S-(n-butyl) benzothioate 
• 2386-60-9 perfluoro-1-butanesulfonyl fluoride 

Relevant articles and documents

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles

H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.

Development of 1-Hydroxy-2(1H)-quinolone-Based Photoacid Generators and Photoresponsive Polymer Surfaces

A new class of carboxylate and sulfonate esters of 1-hydroxy-2(1H)- quinolone has been demonstrated as nonionic photoacid generators (PAGs). Irradiation of carboxylates and sulfonates of 1-hydroxy-2(1H)-quinolone by UV light (γ≥310 nm) resulted in homolysis of weak N-O bond leading to efficient generation of carboxylic and sulfonic acids, respectively. The mechanism for the homolytic N-O bond cleavage was supported by time-dependent DFT calculations. Photoresponsive 1-(p-styrenesulfonyloxy)-2-quinolone-methyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolone-lauryl acrylate (SSQL-LA) copolymers were synthesized from PAG monomer 1-(p-styrenesulfonyloxy) -2-quinolone, and subsequently controlled surface wettability was demonstrated for the above-mentioned photoresponsive polymers. Copyright

Synthesis, photophysical and photochemical properties of photoacid generators based on N-hydroxyanthracene-1,9-dicarboxyimide and their application toward modification of silicon surfaces

We have introduced a series of nonionic photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-hydroxyanthracene-1,9-dicarboxyimide (HADI). The newly synthesized PAGs exhibited positive solvachromatic emission (λmax(hexane) 461 nm, λmax(ethanol) 505 nm) as a function of solvent polarity. Irradiation of PAGs in acetonitrile (ACN) using UV light above 410 nm resulted in the cleavage of weak Na-O bonds, leading to the generation of carboxylic and sulfonic acids in good quantum and chemical yields. Mechanism for the homolytic Na-O bond cleavage for acid generation was supported by time-dependent density functional theory (TD-DFT) calculations. More importantly, using the PAG monomer N-(p-vinylbenzenesulfonyloxy)anthracene- 1,9-dicarboxyimide (VBSADI), we have synthesized N-(p-vinylbenzenesulfonyloxy) anthracene-1,9-dicarboxyimidea-methyl methacrylate (VBSADI-MMA) and N-(p-vinylbenzenesulfonyloxy)anthracene-1,9-dicarboxyimidea-ethyl acrylate (VBSADI-EA) copolymer through atom transfer radical polymerization (ATRP). Finally, we have also developed photoresponsive organosilicon surfaces using the aforementioned polymers.

Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids

Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (≥254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N- phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids.

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.

4-Benzoylbenzoate intercalated in layered double hydroxides: A new catalyst for photo-oxidation of sulfides in solution and in the gas phase

A new mixed organic-inorganic photosensitizer, based on 4-benzoylbenzoate intercalated into a layered double hydroxide has been prepared, characterized and successfully tested for the photo-oxidation of dialkylsulfides, both in acetonitrile and in the gas phase.

Exploiting differences in solution vs solid-supported reactivity for the synthesis of sulfonic acid derivatives

(matrix presented) Quantitative We describe a method herein for the protection of aryl and alkyl sulfonates during synthesis which employs commercially available Wang or MBOH resin, both of which terminate as benzyl alcohols, as both a protecting group and "traceless" linker. Given the known instability of benzylic sulfonate esters to nucleophilic displacement in solution, this linkage is surprisingly stable: no loss of either aryl or alkyl sulfonates is observed when the resin is exposed to a wide variety of organic bases and solvents at room temperature. Further elaboration of the resin-bound sulfonates via Suzuki coupling is also described.

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.