14532-24-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Hexanesulfonyl chloride is used as a sulfonylating agent for the synthesis of pharmaceutical compounds, facilitating the introduction of the sulfonate group into organic molecules to enhance their therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Hexanesulfonyl chloride is utilized as a key intermediate in the production of various agrochemicals, contributing to the development of effective pest control agents.
Used in Synthesis of Specialty Chemicals and Polymers:
1-Hexanesulfonyl chloride is employed as a reagent in the synthesis of specialty chemicals and polymers, where its ability to form sulfonate esters and sulfonamides is crucial for creating materials with specific properties.
Used in Preparation of Sulfonamide Drugs:
1-Hexanesulfonyl chloride is used as a precursor in the preparation of sulfonamide drugs, playing a critical role in the development of antibiotics and other medicinal compounds.

InChI:InChI=1/C6H13ClO2S/c1-2-3-4-5-6-10(7,8)9/h2-6H2,1H3

Upstream product

• 111-31-9 Hexanethiol 
• 6803-40-3 1-hexylthiocyanate 
• 13595-73-8 hexane-1-sulfonic acid 
• 34005-03-3 ((hexylthio)methyl)benzene 
• 2832-45-3 sodium hexyl sulfate 
• 4270-01-3 2-hexylisothiourea hydrobromide 
• 10496-15-8 dihexyl disulfide 
• 111-25-1 1-bromo-hexane 
• 17356-08-0 thiourea 

Downstream Products

• 423-50-7 tridecafluorohexanesulfonyl fluoride 
• 3144-11-4 1-hexanesulfonamide 
• 97526-78-8 Aethyl-4-hexansulfonamidobenzoat 
• 88413-11-0 N-<3-(methylamino)-4-nitrophenyl>hexanesulfonamide 
• 80259-02-5 N-(4-acetamidophenyl)sulfamoylhexane 
• 106273-92-1 Hexyl-sulfonsaeure-<4-nitro-phenylester> 
• 65269-96-7 hexane-1-sulfonyl fluoride 
• 95953-92-7 Tris-<4-nitro-phenoxy>-phosphazosulfonylhexyl 
• 101957-73-7 N--hexan-sulfonimidsaeure-(1)-<4-nitro-phenylester> 
• 95805-83-7 Trianilinophosphazosulfonylhexyl 
• 13002-01-2 chlorosulfuric acid pentafluoropropenyl ester 
• 1216905-10-0 benzyl 3-O-benzyl-6-O-hexylsulfonyl-D-glucopyranoside 
• 96198-84-4 (4-Hexansulfonamidobenzoyl)hydrazin 
• 355-46-4 perfluorohexane-1-sulfonic acid 

Relevant academic research and scientific papers

From off-to on-target: New BRAF-inhibitor-template-derived compounds selectively targeting mitogen activated protein kinase kinase 4 (MKK4)

The mitogen-activated protein kinase (MAP) kinase 4 (MKK4) was found to be a major regulator of liver regeneration and could be a valuable drug target addressing liver related diseases by restoring its intrinsic regenerative capacity. We report on the synthesis and optimization of novel MKK4 inhibitors following a target-hopping strategy from the FDA-approved BRAFV600E inhibitor PLX4032 (8). Applying an iterative multi-parameter optimization process we carved out essential structural features yielding in compounds with a low nanomolar affinity for MKK4 and excellent selectivity profiles against the main off-targets MKK7 and JNK1, which, upon relevant inhibition, would totally abrogate the pro-regenerative effect of MKK4 inhibition, as well as against the off-targets MAP4K5, ZAK and BRAF with selectivity factors ranging from 40 to 430 for our best-balanced compounds 70 and 73.

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.

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.

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%.

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.

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.

A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides

This study describes a new and advantageous procedure for the synthesis of alkanesulfonyl chlorides (2) by the reaction of alkyl thiocyanates (1) with sulfuryl chloride in a mixture of acetic acid and water. The alkanesulfonyl chlorides were obtained in good yields.

Pharmaceutical Compositions Based on Fluorinated Sulphamides and Sulphinimides

Pharmacuetical composition comprising compounds of formula (I): [in-line-formulae]NZ1Z2Z3 ??(I) [/in-line-formulae] in which: Z1, Z2, Z3 each independently of the others represents: a hydrogen atom; C1-C6-alkyl group; a group —SO2R3 wherein R3 represents a linear or branched C1-C12-alkyl, -alkenyl or -alkynyl group, a C3-C10-cycloalkyl group or a C6-C10-aryl group, a (C1-C6)-alkyl-(C6-C14)-aryl group, or a C5-C10-heteroaryl group; it being understood that at least one of the groups Z1, Z2, Z3 represents a group of formula (II) [in-line-formulae]X—RF—(CH2)n—SO2—??(II) [/in-line-formulae] X, RF and n being as defined in claim 1.

N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing

A series of 11 N-sulfonyl homoserine lactones has been synthesised. Some of them were found to competitively inhibit the action of 3-oxohexanoyl-L- homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri. Molecular modeling suggests a possible explanation based on the prevention of structural rearrangements necessary for the formation of the active dimer of LuxR.