N-Propylsulfamide
[CAS# 147962-41-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-Propylsulfamide
• Synonyms: Propylsulfamide
• Molecular Formula: C₃H₁₀N₂O₂S
• Molecular Weight: 138.19
• CAS Registry Number: 147962-41-2
• EC Number: 808-285-0
• SMILES: CCCNS(=O)(=O)N

Properties

• Solubility: Soluble (53 g/L) (25 °C), Calc.^*
• Density: 1.238±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.486, Calc.^*
• Boiling Point: 249.0±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 104.4±22.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

N-Propylsulfamide is an organic compound belonging to the class of sulfamides, which are widely recognized for their versatile biological and chemical properties. This particular compound features a sulfamide group attached to a propyl chain, making it a simple yet effective molecule for various applications. The discovery of N-propylsulfamide emerged from research into the synthesis of sulfamide derivatives, which are known for their potential in pharmaceutical and industrial chemistry.

Sulfamides, in general, are important intermediates in the synthesis of various bioactive compounds. Their structure, which consists of a nitrogen atom bonded to a sulfonyl group and an amide group, allows them to participate in a variety of reactions, such as nucleophilic substitution and electrophilic addition. The introduction of the propyl group in N-propylsulfamide enhances its solubility and stability compared to smaller alkyl sulfamides, which has made it particularly useful in certain chemical and biological contexts.

One of the main applications of N-propylsulfamide is in medicinal chemistry. Sulfamides are known for their antibacterial properties, particularly in the development of sulfonamide-based drugs. N-Propylsulfamide has been investigated for its potential as a precursor in the synthesis of more complex sulfonamide derivatives with enhanced activity against bacterial infections. The compound's ability to interact with bacterial enzymes, such as dihydropteroate synthase, makes it a valuable intermediate in drug development, particularly for designing novel antimicrobial agents.

In addition to its medicinal applications, N-propylsulfamide has been explored as a building block in the synthesis of agrochemicals. The sulfur-containing structure of sulfamides allows them to be used in the development of herbicides, fungicides, and pesticides. By modifying the propylsulfamide structure, researchers can optimize its ability to interact with specific biochemical pathways in plants and pests, leading to the development of more effective and selective agrochemical agents. The relatively simple structure of N-propylsulfamide makes it a versatile starting material for the synthesis of such compounds.

Furthermore, N-propylsulfamide has potential applications in materials science, particularly in the development of novel polymers and coatings. The sulfamide group can act as a reactive site for polymerization, enabling the formation of crosslinked structures with enhanced durability and resistance to environmental factors. This has led to interest in using N-propylsulfamide in the production of specialty polymers for industrial applications, such as in coatings for corrosion protection or in adhesives with high thermal stability.

In summary, N-propylsulfamide is a simple yet versatile compound with a wide range of applications in medicinal chemistry, agrochemicals, and materials science. Its structure allows it to serve as a valuable intermediate in the development of bioactive molecules, while its chemical properties make it useful in the synthesis of functional materials. Ongoing research continues to explore the potential of N-propylsulfamide and its derivatives in various fields, highlighting its importance as a building block in chemical synthesis.

References

2018. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms. Topics in current chemistry (Cham), 376, 6.
DOI: 10.1007/s41061-018-0184-5

2018. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms. Topics in Current Chemistry Collections, 1, 1.
DOI: 10.1007/978-3-030-25598-5_1

2018. Improved and single-pot process for the synthesis of macitentan, an endothelin receptor antagonist, via lithium amide-mediated nucleophilic substitution. Monatshefte fur Chemie - Chemical Monthly, 149, 3.
DOI: 10.1007/s00706-017-2098-2