10151-46-9

Basic information

• Product Name: 2-NAPHTHYLSULFONYLHYDRAZIDE
• Synonyms: 2-NAPHTHYLSULFONYLHYDRAZIDE;AKOS B015546;ART-CHEM-BB B015546;Naphthalene-2-sulfonohydrazide;AK-968/40204653;NSC274887;STK315923;ZINC02566734
• CAS NO: 10151-46-9
• Molecular Formula: C₁₀H₁₀N₂O₂S
• Molecular Weight: 222.26
• Mol File: 10151-46-9.mol
• Article Data: 44

Chemical Properties

• Melting Point: 131 °C(Solv: ethanol (64-17-5))
• Boiling Point: 438.4°Cat760mmHg
• Flash Point: 218.9°C
• Appearance: /
• Density: 1.377g/cm³
• Vapor Pressure: 6.94E-08mmHg at 25°C
• Refractive Index: 1.672
• PKA: 9.45±0.40(Predicted)
• CAS DataBase Reference: 2-NAPHTHYLSULFONYLHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NAPHTHYLSULFONYLHYDRAZIDE(10151-46-9)
• EPA Substance Registry System: 2-NAPHTHYLSULFONYLHYDRAZIDE(10151-46-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 10151-46-9(Hazardous Substances Data)

Usage

Description

2-NAPHTHYLSULFONYLHYDRAZIDE, also known as Naphthalene-2-sulfonohydrazide, is an organic compound with the molecular formula C10H10N2O2S. It is a white crystalline solid that is soluble in water and has a characteristic chemical structure featuring a naphthalene ring with a sulfonyl and hydrazide functional group. 2-NAPHTHYLSULFONYLHYDRAZIDE is known for its potential applications in the synthesis of various chemical compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
2-NAPHTHYLSULFONYLHYDRAZIDE is used as a reagent for the preparation of sulfonated pyrazoles, which are important intermediates in the development of new antibacterial agents. These sulfonated pyrazoles have shown potential in the discovery and synthesis of novel compounds with antibacterial properties, contributing to the fight against drug-resistant bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-NAPHTHYLSULFONYLHYDRAZIDE serves as a versatile building block for the creation of various organic compounds. Its unique chemical structure allows for further functionalization and modification, making it a valuable component in the synthesis of complex molecules with diverse applications.

InChI:InChI=1/C10H10N2O2S/c11-12-15(13,14)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12H,11H2

Upstream product

• 93-11-8 2-Naphthalenesulfonyl chloride 

Downstream Products

• 1393674-72-0 4-(naphthalen-2-yl)-4-phenylbutan-2-one 
• 1554261-74-3 C₂₀H₂₀OS 
• 30166-84-8 2-[(E)-2-phenylethenesulfonyl]naphthalene 
• 1208374-70-2 2-(2-(4-bromophenyl)ethynyl)naphthalene 
• 35330-75-7 2-(methylsulfonyl)naphthalene 
• 1242673-97-7 naphth-2-yl-2’,4’,6’-trimethoxyphenylsulfide 
• 91-20-3 naphthalene 
• 612-78-2 2,2'-binaphthalene 
• 7570-96-9 2-naphthyl phenyl sulfide 
• 52258-16-9 4-methylphenyl 2-naphthyl sulfide 
• 51739-39-0 (4-methoxyphenyl) (naphthalen-2-yl)sulfane 
• 612-94-2 2-phenylnaphthalene 
• 158752-55-7 2-(naphthalen-2-ylsulfonyl)-1-phenylethan-1-one 

Relevant articles and documents

Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water

A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

Electrochemical Annulation-Iodosulfonylation of 1,5-Enyne-containing para-Quinone Methides (p-QMs) to Access (E)-Spiroindenes

A new electrochemical three-component annulation-iodosulfonylation of 1,5-enyne-containing para-quinone methides (p-QMs) has been established by using available arylsulfonyl hydrazides and potassium iodide under environmentally benign conditions. The electrosynthesis offers sustainable and efficient access to construct spirocyclohexadienone-containing (E)-indenes without any additional catalyst or oxidant through a sulfonyl-radical-triggered 1,6-addition and an I+-mediated ipso-cyclization cascade. Notably, potassium iodide plays the triple role of an electrolyte, a redox catalyst, as well as an iodination reagent.

Synthesis of 3,4-Dihydrobenzo[f]phthalazines via Iodine/tert-Butyl Hydroperoxide-Mediated Annulation Cascade of Yne-Allenones

An iodine (I2)/tert-butyl hydroperoxide (TBHP)-mediated annulation cascade between yne-allenones and sulfonyl hydrazides has been established, in which a wide set of dihydrobenzo[f]phthalazines were synthesized through one-pot, two-step strategy under metal-free conditions. The synthetic utility of these transformations leads to subsequent C?C and C?N bond-forming reactions to effectively build up functional aza-heterocycle with potential significance. (Figure presented.).

Gold-Catalyzed Dehydrazinative C(sp)–S Coupling Reactions of Arylsulfonyl Hydrazides with Ethynylbenziodoxolones for Accessing Alkynyl Sulfones

A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.

Electrochemical Sulfonylation-Induced Lactonization of Alkenes: Synthesis of Sulfonyl Phthalides

An electrochemical cascade sulfonylation and lactonization process of alkenes and a most widely used arylsulfonylation reagent─sulfonyl hydrazines─was developed for the first time. This electrochemical sulfonyl lactonization avoided the use of toxic metal

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.