3-Nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide
[CAS# 1228779-96-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: 3-Nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide
• Molecular Formula: C₁₂H₁₇N₃O₅S
• Molecular Weight: 315.35
• CAS Registry Number: 1228779-96-1
• EC Number: 833-813-1
• SMILES: C1COCCC1CNC2=C(C=C(C=C2)S(=O)(=O)N)[N+](=O)[O-]

Properties

• Solubility: Very slightly soluble (0.27 g/L) (25 °C), Calc.^*
• Density: 1.412±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS03;GHS07;GHS08;GHS09 Danger
• Risk Statements: H272-H315-H319-H335-H361-H373-H411
• Safety Statements: P203-P210-P220-P260-P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Oxidising solids	Ox. Sol.	3	H272
Oxidising solids	Ox. Sol.	2	H272
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-Nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide, with the chemical formula C₁₁H₁₅N₃O₅S, is a complex organic compound known for its distinctive chemical structure and reactivity. This molecule features a sulfonamide group, a nitro group, and a tetrahydropyran moiety, making it an interesting subject of study in organic chemistry.

The discovery of 3-nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide is tied to the exploration of multifunctional organic compounds and their applications in medicinal chemistry. Its synthesis involves several steps, beginning with the introduction of a nitro group and a sulfonamide group to a benzene ring, followed by the attachment of a tetrahydropyran-4-ylmethylamino group. This multi-step synthesis reflects the compound's complex structure and functional groups.

One of the primary applications of 3-nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide is in medicinal chemistry, where it serves as an intermediate in the synthesis of pharmaceutical agents. The compound's unique functional groups contribute to its potential as a drug candidate with specific therapeutic properties. For example, the sulfonamide group is known for its role in antibiotic drugs, while the nitro group can be involved in various biological activities.

The compound is also used in the development of targeted therapies. Its chemical structure allows for the design of molecules that can interact with specific biological targets, making it useful in the creation of drugs with high selectivity and efficacy. The tetrahydropyran moiety provides additional structural diversity, which can be leveraged to improve the compound's interaction with biological systems.

In addition to its pharmaceutical applications, 3-nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide is explored for its potential use in other areas of organic synthesis. The compound's functional groups make it a valuable intermediate in the creation of more complex molecules, which can be used in various chemical processes and material science applications.

Overall, 3-nitro-4-[[(tetrahydropyran-4-yl)methyl]amino]benzenesulfonamide exemplifies the complexity and utility of multifunctional organic compounds in modern chemistry. Its discovery and subsequent applications in medicinal chemistry and organic synthesis underscore its importance as a versatile reagent and potential therapeutic agent.

References

2017. Venetoclax. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-22-0046

2019. Synthesis of Venetoclax. Synfacts.
DOI: 10.1055/s-0039-1689868