85-46-1 Usage
Description
1-Naphthalenesulfonyl chloride is a white to beige crystalline powder that undergoes desulfitative carbonylative Stille cross-coupling reaction with tinglucal derivative. It is a chemical compound with the molecular formula C10H7ClO2S and is known for its unique chemical properties.
Uses
1-Naphthalenesulfonyl chloride is used in the preparation of 5'-O-naphthaleneiulfonyldeoxyuridine and 1-sulfonylindazole derivatives. These derivatives are utilized for quantitative metabolome analysis, which is a crucial technique in the study of metabolic pathways and their regulation in biological systems.
Used in Metabolomics Research:
1-Naphthalenesulfonyl chloride is used as a reagent for the synthesis of new sets of isotope reagents, such as 12C4-, 12C2,13C2-, and 13C4-5-diethylamino-naphthalene-1-sulfonyl chloride (DensCl). These reagents, in combination with liquid chromatography Fourier-transform ion cyclotron resonance mass spectrometry (LC-FTICR-MS), are employed for improved analysis of the amineand phenol-containing submetabolome. This application aids in the identification and quantification of metabolites, which is essential for understanding the biochemical processes in living organisms and their response to various stimuli or diseases.
Purification Methods
If the IR indicates the presence of OH, then treat it with an equal weight of PCl5 and heat it at ca 100o for 2hours, cool and pour onto ice + H2O, stir well and filter off the solid. Wash the solid with cold H2O and dry the solid in a vacuum desiccator over P2O5 + solid KOH. Extract the solid with pet ether (b 40-60o), filter off any insoluble solid and cool. Collect the crystalline sulfonyl chloride and recrystallise it from dry Et2O, pet ether or *C6H6/pet ether. If large quantities are available, then it can be distilled under high vacuum. [Fierz-Davaid & Weissenbach Helv Chim Acta 3 2312 1920.] The sulfonamide crystallises from EtOH (m 150.5o) or H2O (m 153o). [Beilstein 11 H 175, 11 II 93, 11 IV 383.]
Check Digit Verification of cas no
The CAS Registry Mumber 85-46-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 5 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 85-46:
(4*8)+(3*5)+(2*4)+(1*6)=61
61 % 10 = 1
So 85-46-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H7ClO2S/c11-14(12,13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
85-46-1Relevant articles and documents
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
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 aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
supporting information, p. 10638 - 10641 (2013/08/23)
A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
supporting information; experimental part, p. 5095 - 5101 (2012/07/28)
Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.