2386-60-9

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Butanesulfonyl chloride is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its application is due to its ability to react with amines to form sulfonamides, which are important in the development of drugs with diverse therapeutic properties.
2. Used in Chemical Synthesis:
1-Butanesulfonyl chloride is used as a reagent in the synthesis of various organic compounds, such as ethyl 2-(1-butanesulfonamido)pent-4-yn-l-oate, 1-butanesulfonamid-N,N′-1,2-ethanediylbis, and 1-butanesulfonamide-N,N′-1,3-propanediylbis. Its application in this field is attributed to its reactivity and versatility in forming different types of chemical bonds.
3. Used in Research and Development:
1-Butanesulfonyl chloride is utilized in research and development for the exploration of new chemical reactions and the synthesis of novel compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals. Its use in this context is due to its unique chemical properties and the possibility of creating a wide range of products through its reactions.

Purification Methods

It has a pungent odour and is LACHRYMATORY. If IR shows OH bands, then dissolve in Et2O, wash with cold saturated aqueous NaHCO3 (care since CO2 will be generated) then H2O, dry it over solid Na2SO4, filter, evaporate and distil the residue twice. Characterise it by shaking a solution in Et2O or *C6H6 with aqueous NH3, collect the solid 1-butanesulfonamide with m 48o after recrystallisation from CHCl3, CCl4 or Et2O/pet ether. [Douglass & Johnson J Am Chem Soc 60 1488 1938, Lee & Dougherty J Org Chem 5 83 1940, Beilstein 4 IV 45.]

InChI:InChI=1/C11H13ClO3/c1-14-10-4-3-8(7-11(10)15-2)9(13)5-6-12/h3-4,7H,5-6H2,1-2H3

Upstream product

• 628-83-1 n-butylthiocyanate 
• 109-79-5 n-butanethiol 
• 544-40-1 Dibutyl sulfide 
• 629-45-8 dibutyl disulfide 
• 2168-93-6 butyl sulfoxide 
• 2386-47-2 butane-1-sulfonic acid 
• 18939-69-0 n-butylisothiouronium chloride 
• 106-97-8 n-butane 
• 55716-09-1 S,S-Di(n-butyl) dithiocarbonate 
• 2386-54-1 1-butanesulfonic acid sodium salt 
• 5184-47-4 benzyl butyl sulfide 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 56-23-5 tetrachloromethane 

Downstream Products

• 109-79-5 n-butanethiol 
• 109-69-3 n-Butyl chloride 
• 660-12-8 n-butyl sulfonyl fluoride 
• 3144-04-5 butane-1-sulfonamide 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 6655-26-1 N-phenylbutane-1-sulfonamide 
• 784189-59-9 (butane-1-sulfonyl)-sulfanilyl-amine 
• 78-40-0 triethyl phosphate 
• 20195-07-7 S-butyl O,O-diethyl phosphorothioate 
• 75-00-3 chloroethane 
• 38804-95-4 butane-1-sulfonic acid phenyl ester 
• 102809-79-0 (butane-1-sulfonyl)-triphenoxyphosphoranyliden-amine 
• 2374-69-8 butane-1-sulfonic acid methyl ester 
• 38789-03-6 Butansulfonsaeure-m-anisylester 

Relevant academic research and scientific papers

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation

Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)-H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams.

Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides

C6F5SO2Cl reacts with organolithiums and organomagnesium halides RM (R = Me, Bu, Ph; M = Li, MgX) to give mainly C6F5H and C6F5Cl. C6F5SO2Br and

Experimental study on deep desulfurization of MTBE by electrochemical oxidation and distillation

With the increasing awareness of environmental protection, deep desulfurization of methyl tert-butyl ether (MTBE), which is the most important octane booster in gasoline, is extremely urgent. Herein, a new desulfurization method, involving the combination of electrochemical oxidation and distillation, is proposed to reduce the sulfur content in MTBE. Under optimum operating conditions, the sulfur content of real MTBE decreases from 132.5 μg g-1 to 2.3 μg g-1 and the desulfurization efficiency reaches 98.25%. The oxidation products with high boiling points can be separated by distillation. FTIR analyses prove that electrochemical oxidation has no influence on the main properties of MTBE. Moreover, GC/MS is used to study the conversion of model organic sulfides (dimethyl disulfide, diethyl sulfide and butyl mercaptan) in the electrochemical oxidative desulfurization process. Finally, the possible reaction mechanism of the electrochemical oxidative desulfurization of MTBE is proposed.

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.

Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation

A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.

Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation

A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T

A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.

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.

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4

A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.