240423-09-0

Basic information

• Product Name: 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE
• Synonyms: N-(3-AMINOPROPYL)-2-NITROBENZENESULFONAMIDE;N-(2-NITROBENZENESULFONYL)-1,3-PROPANEDIAMINE;1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE;1-Amino-3-(2-nitrobenzenesulfonamido)propane N-(2-Nitrobenzenesulfonyl)-1,3-propanediamine N-(o-Ns)-1,3-diaminopropane
• CAS NO: 240423-09-0
• Molecular Formula: C₉H₁₃N₃O₄S
• Molecular Weight: 259.28
• Product Categories: Monoprotected Diaminoalkanes;N-(o-Ns)-diaminoalkanes
• Mol File: 240423-09-0.mol

Chemical Properties

• Boiling Point: 448.997°C at 760 mmHg
• Flash Point: 225.346°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.18±0.40(Predicted)
• CAS DataBase Reference: 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE(240423-09-0)
• EPA Substance Registry System: 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE(240423-09-0)

Safety Data

• Hazardous Substances Data: 240423-09-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE is used as a key intermediate in the synthesis of new drugs, contributing to the advancement of pharmaceutical chemistry. Its unique structure allows for the development of compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE serves as a crucial component for creating a variety of complex organic molecules. Its reactivity and functional groups enable the formation of diverse chemical products.
Used in Chemical Product Manufacturing:
Beyond its applications in pharmaceuticals and organic synthesis, 1-AMINO-3-(2-NITROBENZENESULFONAMIDO)PROPANE is also utilized in the manufacturing of other chemical products, highlighting its broad applicability across different industries.

InChI:InChI=1/C9H13N3O4S/c10-6-3-7-11-17(15,16)9-5-2-1-4-8(9)12(13)14/h1-2,4-5,11H,3,6-7,10H2

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 109-76-2 Trimethylenediamine 

Downstream Products

• 240423-18-1 N-(tert-butoxycarbonyl)-N'-(2-nitrobenzenesulfonyl)-1,3-propanediamine 
• 318466-85-2 3-[{3-[(5-bromopentyl)(2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]-N-[3-(2-nitrobenzenesulfonylamino)propyl]butyramide 
• 318466-89-6 3-[{3-[[5-(tert-butyldimethylsilanyloxy)pentyl](2-nitrobenzenesulfonyl)amino]propyl}(2-nitrobenzenesulfonyl)amino]-N-[3-(2-nitrobenzenesulfonylamino)propyl]butyramide 
• 312283-38-8 N-[3-(2-nitrobenzenesulfonyl)amino-propan-1-yl]-1H-indole-3-acetamide 
• 312283-45-7 N-(2-nitrobenzenesulfonyl)-N'-(allyloxycarbonyl)-1,3-diaminopropane 
• 349649-34-9 N-(4-methoxy-3-methylcarbamoyl-phenyl)-N'-[3-(2-nitro-benzenesulfonylamino)-propyl]-oxalamide 
• 437718-40-6 N-(2-nitrobenzenesulfonyl)-N'-(benzyloxycarbonyl)-1,3-diaminopropane 
• 906734-90-5 N-[3-(2-nitro-benzenesulfonylamino)-propyl]-propionamide 
• 1026499-15-9 7-(allyloxycarbonylamino)-4-(2-nitrobenzenesulfonyl)-4-azaheptan-1-yl bromide 
• 1026386-49-1 {3-[{3-[[5-(2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-pentyl]-(2-nitro-benzenesulfonyl)-amino]-propyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid allyl ester 
• 1054656-12-0 C₆₂H₇₈N₁₂O₁₉S₂ 
• 437718-27-9 7-((benzyloxycarbonyl)amino)-4-(2-nitrobenzrnesulfonyl)-4-azaheptan-1-yl bromide 
• 437718-39-3 methyl 7-(2-nitrobenzenesulfonylamino)-4-(benzyloxycarbonyl)-4-azaheptanoate 
• 437718-33-7 7-(2-nitrobenzenesulfonylamino)-4-(benzyloxycarbonyl)-4-azaheptanoic acid 

Relevant articles and documents

Heteroatom-embedded medium-sized cycloalkynes: Concise synthesis, structural analysis, and reactions

A variety of medium-sized cycloalkynes were efficiently synthesized by the double Nicholas reaction of cobalt complex and bis(hetero)substituted acyclic compound. The alkyne moiety within the ring has a unique bent structure and high reactivity toward cycloaddition reactions. Furthermore, preparation of multifunctionalized alkynes was achieved by embedding the cycloalkyne within a peptide chain.

Novel preloaded resins for solid-phase biotinylation of carboxylic acids

Use of solid-phase synthesis for the derivatization of carboxylic acids with biotinylated spacers consisting of ethylenoxy units is described. An aminomethylated resin provided with an acid-labile aldehyde linker is used as the polymer support and three different systems with a reactive amino group are introduced. Acylation of each system was tested with a set of model carboxylic acids and afforded crude products of excellent purity. The preloaded resins are similar to the Biotin-PEG-NovaTagTM resin but offer several advantages including simple elongation of the spacer arm. The protocols described represent a very efficient way of modifying compounds to obtain ligands for affinity chromatography studies.

Syntheses and biological activities of fluorescent-labeled analogs of acylpolyamine toxin NPTX-594 isolated from the venom of Madagascar Joro spider

Acylpolyamine-type spider toxins are known to be potent and specific blockers against glutamate receptors (GluRs). The present study describes the syntheses and biological activities of several fluorescent-labeled analogs related to a Madagascar Joro spider toxin NPTX-594 to analyze visually the unknown interaction between spider toxins and GluRs.

Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range.

Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles

A versatile synthetic route to potentially useful fused-ring [1,2,4]thiadiazole scaffolds (e.g., 7a and 10b) via exchange reactions of the precursor [1,2,4]thiadiazol-3-(2H)one derivatives (e.g., 6 and 9) with appropriately substituted nitriles (e.g., cyanogen bromide or p-toluenesulfonyl cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively derivatized at the N1 and/or N2 positions in a linear fashion. The X-ray crystal structure of the 3-methyl bicyclic [1,2,4]THD (21) was obtained, and selective methylation at the N1 position via a protection-alkylation-deprotection protocol, as illustrated in Scheme 6, was confirmed. Alternatively, a short convergent synthesis of N1-functionalized derivatives from the reaction of 10b with appropriately substituted secondary amines was also developed. Hence, these synthetic strategies were advantageously exploited to provide access to a variety of diversely derivatized 3-substituted fused-ring [1,2,4]thiadiazole derivatives.

The choice of phosphane reagent in Fukuyama-Mitsunobu alkylation: Intramolecular selectivity between primary and secondary alcohols in the preparation of asymmetric tetraamine building blocks for synthesis of philanthotoxins

Philanthotoxin-433 (PhTX-433) is a polyamine wasp toxin that antagonizes certain ionotropic receptors noncompetitively. Four analogues of PhTX-433, C-methylated in the polyamine chain, were synthesized from (RS)-1,3-butanediol, two diamine building blocks, and an activated/protected tyrosine derivative. Use of a phosphane reagent more bulky than trimethylphosphane gave a high intramolecular selectivity between primary and secondary hydroxy groups in the Fukuyama-Mitsunobu reaction. Thus, trimethylphosphane proved to be the only phosphane reagent that enabled alkylation of 2-nitrobenzenesulfonamides with a wide range of secondary alcohols, whereas tributylphosphane was selective for primary alcohol groups. This selectivity was utilized to obtain orthogonally protected, asymmetric, branched tetraamines, employed for solution-phase synthesis of philanthotoxin analogues. The branched philanthotoxin analogues thus obtained were tested in an electrophysiological assay using rat brain ionotropic glutamate receptors expressed in Xenopus laevis oocytes. Their potencies proved to be similar to the corresponding nonbranched analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy

Total synthesis of spider toxins HO-416b (1) and Agel-489 (2) was accomplished using the 2-nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. In this strategy, the C-N bonds were constructed by alkylation of sulfonamides with alkyl halides or Mitsunobu reaction with the corresponding alcohol. Beginning with monoprotection of the symmetrical diamine, the construction of the backbone from diamine 3 was efficiently accomplished in 7 steps for 14 and 9 steps for 29. Removal of the Ns group while the substrate was attached to a novel solid support enabled the efficient isolation of this highly polar compound.

Total synthesis of polyamine toxin HO-416b utilizing the 2- nitrobenzenesulfonamide protecting group

The total synthesis of HO-416b (1) was accomplished using the 2- nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. Starting with monosulfonylated diamines 2 and 3, three C-N bonds were constructed via alkylation of sulfonamides with alkyl halides. Removal of the Ns groups while the substrate was attached to a novel solid support enabled the efficient isolation of pure 1.